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Beyond the Uniform

Beyond the Uniform is a show to help military veterans navigate their civilian career. Each week, I meet with different veterans to learn more about their civilian career, how they got there, and what advice they'd give to other military personnel.
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Now displaying: August, 2017
Aug 30, 2017

"No matter what job you're doing or where you're going, you always want to be the best at your current role. I never imagined that I'd be in the sports industry, let alone the President of an NHL Hockey Team. I never imagined that I'd be at Goldman Sachs. When I was in the Army I just worked really hard, and then identified that my next step would be getting into the best grad school, and then I just focused on that. You just have to have this balance of short term and long term planning."
- Matthew Caldwell

Matthew Caldwell is the President and CEO of the Florida Panthers and Sunrise Sports & Entertainment. Matthew started out at West Point, after which he served in the U.S. Army for five years, conducting combat operations in Iraq and peacekeeping operations in Kosovo. Matthew worked as a Vice President at Goldman Sachs in their Investment Management Division, and then transitioned to Chief Operating Officer for the Panthers before being elevated to President and CEO. Matthew holds a JD/MBA from Northwestern University School of Law and the Kellogg School of Management

Our Sponsor:

  • Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at BeyondTheUniform.io/books

Selected Resources

  • A guy that I most recently have really started following and has been Simon Sinek. About six months ago I found him, and he's done so much research and it's not specific to sports, or finance, or technology. His TED talk is: Start With Why - it's why great leaders inspire people to take action. It's a simple kind of concept but it's all about understanding why you exist. Whether you're working at Apple or wherever you have to figure out why... your purpose... your vision for the future. These are things we kind of did in the military but it's so important. A company like Apple, they exist because they're always challenging the status quo.  The book is fascinating because he covers sports teams, Martin Luther King, Google, Apple... it's very interesting.
  • He also has another book - Leaders Eat Last. I think people in the military will appreciate it.
  • iv'e gotten into sports books - culture and how people operate is so important to them. I read recently the Real Madrid Way - its the most valuable sports franchise out there. Steven Mandis is a Goldman alum too, and i reached out to him and we talked for an hour about why Real Madrid was so valuable and what they've done in the community.

Show Notes

Please note that I type these notes during the interview so there are likely to be misspellings, grammatical errors, and misquotes. This is not meant to be a verbatim account of our conversation, but a VERY basic text transcript of our discussion.

  • How did you approach the decision to leave the Army?
    • It was the toughest decision I've ever had professionally. I went back and forth on it a bunch of times. I was in the Army for five years - the first three I was deployed, in Iraq, Kosovo, or a build up for that. It was very high tempo. Ironically, when I was deployed, I actually really enjoyed it and felt like I was making a difference and serviging a highe rpurpose. When I got back, I was stablized for a year, the garrison lifesytle at my base in Germany. I went back and forth for a year but realized I enjoyed teh Army most during dpeloyments, and that's not all the time. I didn't know if I wanted to go special ops and sustain that op tempo for long-term. Ultimatley I decided I wanted other things besides the Army. I didn't think I could deploy every year even though I enjoyed it. I thought graduate school was a natural next step and then se
  • How did you decide on a JD / MBA program?
    • I always liked business and reading the Wall Street Journal and hearing what companies are doign and reading Good to Great. I thought an MBA was very suitable in opening me up to different industries. When I started researchign schools Noerthwestern was my top pick - I love the Chicago area and their culture. They ahve this very integrated, but also very exciting JD/MBA program that was in three years. I thought I'd get a taste of both business and law. I applied to a bunch of buisness schools and thought if I could also get a law degree it'd make me better at busienss or maybe I'd like law instead. Most programs are around four years and it's a lot of money. For me it was a good fit.
    • For advice for other veterans, it really did work out for myself. I had all this leadership experience, I had lived overseas and had a good world view. So I had a good view of what was out there - for me to come home, as much as I had an interest in business I had no idea if I would be a consultant, a lawyer, finance - I was all over the map. For me it was a three year reset. And the networking aspect was most important. If you go to West Point for four years and then five years in the army, that's nine years of uyour life (one third of your life at that point) where you're just with a mlitary segment. It's a secdluded world. To get out and meet people from different backgrounds, hear about what they did and what they did in the workforce, that experience was very eye opening to me. I learned what they did and they were a great resource. It was the perfect transition point for me.
    • Some of my friends got work experience before grad school and I can see the value of that. When people were talking about a case study, i didn't have any context for what they were talking about.
  • What lead you to Goldman Sachs?
    • Most people in business school go to all the networking events, take classes, talk to people and build from the bottom up. I want to be in Private Equity, in the MErgers & Acquisition world. They identify an industry and then start interviewing in certain geographic areas. I looked at I knew I wanted to go to business and enjoyed those classes and then - what company do I want to be most associated with. I did an exhaustive search and talked to consulting companies, and General Electirc, Proctor and Gamble, etc, but I felt like I connected with the banks. I like JP Morgan & Chase, Goldman, etc - I connected with the people at Goldman. They were diverse, hardworking, and wanted to be in an environment like that.
    • There were three areas: the trading side of the house, i enjoyed that mentality but didn't know long term. Investment banking house where working on big deals with major institutions. But ultimately the investment management division was a good balance between working with big institutions on how to invest their capital but also resonate with me long term.
    • There were a few West Point guys who mentored me.
  • For someone on active duty, how would you explain the work you did at Goldman Sachs?
    • It is a great firm - over many generations they've produced great people who have done great things for the country.
    • My every day life there I worked on a team with about six individuals managing thirty or so accounts. Big families, foundations, non-profit, another company's assets, etc. We were the intermediary between the client - what are their needs, what are they trying to do - and then sit with all the experts at the firm (in research, or investing in Europe, or Latin America, etc). We'd be the intermediary between them and the resources at Goldman. A lot of my job was listening to my clients, hearing their needs, running around and talking to different departments and then making recommendations.
  • What advice do you have for a veteran aspiring to work at Goldman Sachs?
    • The banks or any firms on Wall Street generally like military. They appreciate the tenacity, the hardwork, the comraderie - the characteristics of many service men and women. You put the organization first. The company is more important than the individual. That's not common everywhere. A place like Goldman really values that. It is a tough firm to get into - they usually only hire right out of college or an MBA or other graduate program. They value talent and intelligence and very diverse backgrounds.
    • If you have an interesting story and they think you can add a lot of value at the firm, they know they can teach you all the finance technique. It's just a matter of hustling to get in front of the right people. I've gone through a job search a lot of times - it's a matter of reading and talking to the right person. Sometimes you do 20 coffee chats and yuo don't feel like you're making any progress, and then the 21st meeting and it's the perfect meeting. but if you didn't go through all the reps before that you don't know how it would have worked out.
    • I was at school in Chicago and was interested in going to New York. And I wasn't able to get a time to meet with anyone else. I sat at Starbucks all day emailing people and calling them and I figured since I was in NY I might as well try to meet with people. And that got me in touch with someone who was at Credit Suisse who was West Point, he had a few minutes available and I sat down with him. I was open and honest that Goldman was my first choice,; and he introduced me to someone at Goldman. 30 interviews later I got a job there.
  • What lead you to make the transition to the Florida Panthers?
    • I was at Goldman and one of the unique aspects of their culture is that the junior people are the ones who are encouraged to get out there and kick up new business. Typically in firms more senior partners are trying to drive new client relationships. At Goldman they send out their more junior folks. So I was out there talking to institutions and big family offices trying to get them to invest at Goldman. So I was out there hussling and same thing as I did whe ntrying to get my first job. I started a relationship with another West Point grad, Vincent Viola. he ended up becoming a client at Goldman, and was great at investing his capital. We built this great report with him over time and he took a liking to me as a younger West Pointer who got his start on Wall Street. It was very familiar with his background. He went trading and came from Brooklyn (I'm from Staten Island). After a few years he asked me to come and join his family office. So I jumped at the opportunity. As much as I loved Goldman I thought it was something I couldn't' pass it up.
    • I was dreading going to the guy who hired me and probably got ten seconds into my pitch and he said, 'I would love for you to build a career here, but you gotta jump on this.' So i started working directly for Vinnie. He had purchased the Florida Panthers hockey team. He always wanted to get into sports - it's hockey in South Florida, which is tough. We knew there would be a big challenge, he said, I'm a very hands on operator and could use someone I could trust.
    • I signed up for it, and moved down to South Florida. I live in Miami, started off being an ownership representative giving him advice on how to improve the franchise. how to sell season tickets and get the stadium packed. They ended up giving me the COO role as a permanent role. As the franchise turned around 1.5 years later, and he named me the CEO and President.
  • How would you explain your role as CEO?
    • I was a huge sports fan of every sport. There's actually another West Point graduate, Eric Joyce, who was an Assistant Captain for the West Point hockey team. Eric was his guy to help out on the hockey side. And he's done a great job and is the assistant GM. Initially I focused more on the business side - it was more selling the team and keeping the budget straight and sending reports to people about our marketing plan and sales plan. everything that happens off the ice.
    • Right now there's different periods where things change dramatically. We're in the office season so things aren't top of mind for people. However, for the business side of the operation its an important time to knock out some long-term projects. A big thing we're doing right now is formalizing our marketing plan, getting feedback from all the different departments on what will be our slogan this year, how to attract more fans, how to get a big excitement around opening night. It comes on October 7 and so we hit the pause button and think about our identify, our team and how to tell our story to our fan base.
    • We're also very active in our grassroots - sports aren't front of mind - we go door-to-door and go to local boys and girls club events and anything to support our team and show our presence. There's more of an emotional presence between the team and the community
    • After labor day the whole coaching staff and players and hockey side comes and then its about supporting the training camp. And it's ver intense and we want to make sure the fans have a great experience. Visiting suites and clubs and showing them a great time in the stands.
    • Additionally, I'm President of Sunrise Sports & Entertainment that operates  - we got Bruno Mars and John Mayer coming through. All the ushers, all the ticket tapes, all the people who run food and beverages. We want to make sure they have a great experience.
  • What advice do you have for a veteran seeking a career in the sports industry?
    • I don't know if it differs much from other industries. a lot of companies value how interested you are in something, and if someone is leaving the military in six months you need to start reaching out to sports teams or anyone who has any connection there. Go on LinkedIn or Facebook see who you know - give them a call. Start hearing things. See if that sounds interesting. Do you know anyone in the NY area? Get introduced and start having that conversation. Any industry will respect a veteran reaching out. It's not that you have to prove anything. They won't hire you because of your specific job in the military they just want to know you did a great job. No matter what job you're doing or where you're going, you want to be the best at your current role. You can fall into the mistake of coasting or thinking of what you'll do next. The problem is you never know where your career will take you, and it's important for recommendations and when you want to tell stories in interviews and why you did a great job in the current job where you are. Just worked really hard and identified my next step and just focused on that. You gotta have a balance of short term and long term. Research industries, do a great job.
  • What resources - books, programs, seminars, conferences - have helped you in your civilian career that you would recommend to other veterans?
    • A guy that I most recently have really started following and has been Simon Sinek. About six months ago I found him, and he's done so much research and it's not specific to sports, or finance, or technology. His TED talk is: Start With Why - it's why great leaders inspire people to take action. It's a simple kind of concept but it's all about understanding why you exist. Whether you're working at Apple or wherever you have to figure out why... your purpose... your vision for the future. These are things we kind of did in the military but it's so important. A company like Apple, they exist because they're always challenging the status quo.  The book is fascinating because he covers sports teams, Martin Luther King, Google, Apple... it's very interesting.
    • He also has another book - Leaders Eat Last. I think people in the military will appreciate it.
    • iv'e gotten into sports books - culture and how people operate is so important to them. I read recently the Real Madrid Way - its the most valuable sports franchise out there. Steven Mandis is a Goldman alum too, and i reached out to him and we talked for an hour about why Real Madrid was so valuable and what they've done in the community.
  • Final words of wisdom?
    • Taking a risk. Quick anecdote, when I was in business school I was able to sit with the student admissions team. I sat in the room and heard right from the Director of Admissions who was letting people into Kellogg. And they said they see resumes from veterans and have no idea what it says. As much as we try to dumb it down and not use acronyms, it still sounds foreign to people. It's difficult to pull info out of veterans. We're trained to always put the organization first and focusing on the unit. We're trained not to self promote. It's a tough thing to do - you've gotta spread the needle about promoting yourself and clal someone and explain why they should take your call or why they should get on the phone with you.
    • As a veteran you don't want to ask for favors - you want to be rewarded for performance without pounding your chest. It's this difficult balance. IF you feel like you're self promoting you probably arne't- it just isn't. if you don't do it, no one will.
Aug 23, 2017

"I spent about $1,800 buying bags and thinks, built my own website and started trying to sell coffee online. So basically I started Black Rifle Coffee from a passion that I sought to test out."
- Evan Hafer

Evan Hafer is the Founder & CEO of Black Rifle Coffee, a small batch coffee roasting company. He started out at the University of Idaho, after which he spent 14 years in the U.S. Army as an infantryman, a Special Forces soldier, and a CIA contractor.

I came across Evan in a 2016 Forbes Article about the Top 25 Veteran Founded Startups in America.

Our Sponsor:

  • Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at BeyondTheUniform.io/books

Selected Resources

  • Forbes Article about the Top 25 Veteran Founded Startups in America.
  • Coursera is fantastic. It has an online catalgoue from Penn State, Stanford, Michigan. I signed up for courses from Wharton. It's a great outlet. YOuv'e got a lot of access to Coursera.
  • Udemy is another great online learning - courses from specific personalities.
  • Lynda is a fantastic resource - it's amazing.
  • The first thing I do is google it and then take a course on it. How do I built a dashboard with my KPIs based on division. I can't tell you how to do that based on military experience - but I can google this and find classes on how to plug this in. It may take a few days - you can't be too impatient.
  • One of the best books I've read - Good to Great and Built to Last. I've read Good to Great - listened to it or read it, probably six times. These are some of the best books that I've read.
  • Podcasts: every day I can get into a half hour on marketing, or leadership / management - any time I can spend 30 minutes listening. It might not be the most sage advice at that time, who knows what type f

Show Notes

Please note that I type these notes during the interview so there are likely to be misspellings, grammatical errors, and misquotes. This is not meant to be a verbatim account of our conversation, but a VERY basic text transcript of our discussion.

  • How did you make the decision to leave the Army?
    • Jioned National Guard in 1995 while in College. Was still in 2015. 20 years in active duty or in the reserves, and 8 years with the CIA as a contractor
    • Had been thinking about it for 2 years. I had another business in Idaho - fly fishing, white water rafting, etc. I was planning on getting out and going to grad school or something like that. I was burnt out on deployments, coming up on 20 years of military service and wanted a change
  • What was your first job search like out of the Army?
    • I didn't really have one. I knew I was going to start my won business. I had been roasting coffee for ten years in Iraq and Afghanistan. I had purchased another company a few years before. I wasn't thinking of doing an online roast to order coffee company. My wife and I were thinking of opening a coffee shop. We had gone back and forth on what he had wnated to do. Ultimately we wanted to try to test the market. Didn't want to spend $100k trying to get a coffee shop. Ultimately, I wasn't sure if we could make it work. I could build a website and invest a limited amount of capital - I spent about $1,800 byying bags and thinks, built my own website and selling coffee online
  • What was the genesis of Black Rifle Coffee?
    • I was roasting enough coffee at the time for a few different restaurants and few friends. When I stood up the website and started selling online, after my first month I repaid the money I paid into the company. I was fairly convinced at the end of first month
  • For veteran listeners, how would you describe Black Rifle Coffee?
    • A lot of people say, I need a full blown business plan. Well, I'm a military guy and we go through a lot of planning and cycles around the planning. Every plan doesn't survive first contact. It's fine to do a five paragraph mission order, but the mission statement can't be around the idea - it needs to be around your life. My mission statement was: I will become economically emanicapted from the government and be able to feed my family through my own endeavor. Then I put out a combination of things I could do iwthin this operatino order. A lot of guys become wrapped around a tactic - I have to be THIS. I didn't I was just attached to the idea of being free from the US goverment and drove into marketing and branding and tact. If I can market one of the skills I have - I was roasting coffee and doing outdoors-e stuff. Black Rifle COffee was built out of these two things. Then I started to get a positive Return On Investment really early. If I spend $10 I can make $20... i can actually make a profit. Especially if I start to scale. I started in my garage with $1,800. I didn't hire any employees for my first year. Just me and my wife (part time for about 6 months of that firs tyear) . I was doing customer service, packaging and shipping, photography, social media, website. I was a one-man show. A lot of guys thought that seemed fairly difficult. I only slept about four hours a night for th efirst year of the business - 7 days a week. I had a thermarest in my office. I hired employee #1 after the first year. After the second year I ahd 26 employees. Now I have 84 employees. I've never taken out any debt in my company - no investment. I run it completely off it's own profit margins. I've scaled the company, continued to purchase everything and anything through the profit.
    • I can beat up my employees over $0.03 and a box. If I'm going to buy 12 tonnes of cardboard from China I know exactly how much that will be. There is nothing I wouldn't tell you about this business. I can tell you down to the cent for the last 2.5 years.I'll spend an hour or two in fulfillment, and hour or two in purchasing. Just packing a box and understanding exactly how I want the product to be displayed when it hits their doorstep. The customer needs to understand that no detail can be overlooked. I try to drive a detail oriented ship. We miss things but it's not because we're not trying it's because when you send out a few thousand shipments a day, you miss a few things. It's not as precision as I'd like it to be.
  • At what point were you able to start paying yourself a salary?
    • 14 months - it was a few thousand dollars a month. Now, we'll do over $20M annual this eyar, and I still only pay myself $70k. I went from $2k to $4k in increments. But I've only paid myself for over one year in the last two and a half years. The more money you take out of a business the less it will grow. A lot of guys make this mistake really early. We sold two houses, and my wife and I went from making $250,000 per year as a high paid contract for the government to making NOTHING. For over a year nothing. I had sold two houses, a truck, all my guns, just to keep going. My wife was ready to kill me. It's definitely worth it. I've got a 40k square foot building a 60 kilo roaster - all of them are
  • What did you do on Active Duty to help in startups?
    • I was doing payroll in mission planning and our budget for our small indigineous force. I thought, if I can run this Afghan with a third grade education, if I can train them to do these multi-level kinetic operations this can translate to business. I thought of it as a small business. If you don't run your budget in a strict and proficient way you're setting yoruself up for your own failure.
    • I had the unique opportunity of working with some guys who had run a small business. My original mentor was a SpecOps guy and he transitioned to a small business. It was always in the back of my mind - I was going to be a business owner. Every part of my service - how does this translate into the business world. When I transitino out I need to be able ot translate this into something I can monetize.
    • Not - I need to be able to tell these stories. How do I take these skills and use them on the outside? They're very unique skills that very few people acquire. Military people are some of the most complex problem solvers in the world. When I look at my service - always look tot ranslate what you're doing now into what you're doing
    • Seek professional development opportunies. Seek some skills that the military can pay for but it might not be translatable to your MOS right now but how about your future. I went to a lot of schools when I was in and would come back when I was home and take professional development training. There's this total access to online learning There are so many different ways you can learn that you don't need the US military - but you have the ability to have the military pay for all the training you want to do. I've sat in on university classes to learn about economics
  • Resources
    • Coursera is fantastic. It has an online catalgoue from Penn State, Stanford, Michigan. I signed up for courses from Wharton. It's a great outlet. YOuv'e got a lot of access to Coursera.
    • Udemy is another great online learning - courses from specific personalities.
    • Lynda is a fantastic resource - it's amazing.
    • The first thing I do is google it and then take a course on it. How do I built a dashboard with my KPIs based on division. I can't tell you how to do that based on military experience - but I can google this and find classes on how to plug this in. It may take a few days - you can't be too impatient.
    • One of the best books I've read - Good to Great and Built to Last. I've read Good to Great - listened to it or read it, probably six times. These are some of the best books that I've read.
    • Podcasts: every day I can get into a half hour on marketing, or leadership / management - any time I can spend 30 minutes listening. It might not be the most sage advice at that time, who knows what type f
  • What has been the most challenging moment to date?
    • WHn you have 80 people who work fory ou you develop personal relationships with them. It's an ecosystem - people rpovide the balance in the ecosytem. Terminating people or repurosing them - having really frank discussions with people in general about work performance. These are incredibly difficutl things to do. A loto f business owners avoid tough discussions with employees, and I know why. I want the best for people - however, some people will never conform to the environemnt you're trying to build. You may love them and appreciate them - but they may not be a good fit for the ecosystem. The ahrdest part is managing people - it's very difficult. Knowing you like people but they don't fit into your company this is a really difficult challenge. Because the company's ecosystem always has to be in balance. Hire slow, fire fast. It doesn't mean firing will be easier but yo have to do it to grow the company.
    • A redwood grows really well in a redwood forest. It doesn't grow really well in Sonora. Just becasue they don't fit in in your company doesn't mean they won't fit in somewhere else. They'll be good people wherever they go. It might not be a good cultural fit. We tend to over exagerate people's failures - it may not be a failure on either part it may just be confomring to the envirnonemnt. It's a difficult part for managers - you're done here. I try to say this sin't a good fit how do we make you succeed somewhere else.
  • What has been the most rewarding moment to date?
    • Not just one moment - I always tell people when I was in the government it wasa  pleasure to serve the country. But I got to the point where Iw asn't enjoying my job or my profession. Here right now in my life, I go from my house - two little girls 3.5 and 8 weeks, a beautiful wife and a loving household. And I go to my place of work, ten minutes away, full of people who are competent and they love me and I love them. Every corner of my life - even though there is stress - there is great people and nothing in my life doesn't insprie me at this point. I don't drag my feet going anywhere. I've never had that before. It's very strange to look forward to every day or every minute of my life. I think that's the greatest achievement I've had - I've been able to rapidly change my life. A lot of my professional life i was unhappy - now every day is a challenge. The people around me are fantastic and excellent people. It's so rewarding to know I looking forward to it.
    • I started with my goal of economic freedom. Everyone needs to define what happiness looks like. I love to work, the art of business. But I love rolling up my sleeves and going to work. So happiness - I'm emanicipating myself from government service. I need to create enough welath to become happy. A lot of people say happiness is about wealth or a means to an end. If you're not happy along the way - yo have to enjoy the mountain climb not just the summit. YOu can't just look back - oyu have to enjoy the climb.
  • What advice do you have for veterans thinking of starting their own company?
    • You have to be dedicated to being a business man. Even though you served you country and that's an admiral thing, the people of the United States don't owe yuo anything. I'm not trying to be negative - you have to be able to translate things into a new profession. You need to concentrate on the future not what you've done in the past. You need to find what you've done in the past you can leverage to be a better busienss person. You have to be humbled at the alter of business - the world doesn't owe you anything. It doesn't owe you anything. It helps you've got dedication and complex probelm solving skills. You need to be more committed to this than anythign else you've done before. Themost stress I've experienced wasn't being shot at - it was having a wife and child at home and knowing they have to be fed and what I did on a daily basis was going to provide a good or bad life for them. That's the most stress I've had in my life - it's constant and heavy. You have to dedicate yourself, and humble yourself. You have to take it on like you've never taken on in your life. you have to be so committed to it - you have to prepre for the worst and hope for the best
    • In many ways you're discounted because of your service - you don't have any business experience
  • What does the next 12 months look like for BRCC?
    • We're going to move out of Salt Lake to another state. We're moving the corproate headquarters to Colorado Springs. The enxt twelve months we'll open up 12 brick and mortar stores, logistics in different states and state specific roasters. And we'll have some joint projects going on with some veteran companies. And I think the next twelve months will be really big.W e launch our franchise initaitive in 18 months. Th enext twelve months will be a lot of work, we'll expand quite a bit. The big expansion is september of next month.
Aug 16, 2017

"It was like an apocalypse movie and it was the day we launched Plated - the worst day in the history of the internet. And then our cargo container got picked up in the storm surge and sucked out into the river. The only thing that kept our business from getting flooded out of business was that thumb width 220V electricity cord that got tangled around a phone pole and didn't get sucked out to sea. It was just a lesson in perseverance."
- Nick Taranto

Nick Taranto is the Co-Founder & CEO of Plated, a company whose "Mission is to Help People Eat Better, and Live Better." Plated has raised over $55M in funding, and been featured in the Wall Street Journal, Forbes, NYT, Wired Magazine and more. He started out at Dartmouth College, after which he worked at KOMPIP Microfinance before going on to Harvard Business School. After HBS, he graduated from the Marine Corps' The Basic School, where he Drilled as an active reservist for 3 years. He also worked at Goldman Sachs as a Private Wealth Advisor prior to starting Plated.

Our Sponsor:

  • Audible is offering one FREE audio book to Beyond the Uniform listeners. You can claim this offer here, and see a list of books recommended by my guests at BeyondTheUniform.io/books

Selected Resources

  • There's a great book by Ben Horowitz at Andreesen Horowitz - the hard Thing About Hard Things. Before becoming a VC, he was an entrepreneur and started a few businesses. He talks through his experience and takeaways for aspiring entreprenerus.
  • A resource I go back ot again is entrepreneur.com - you have to sift through some of the news, but there are a lot of great articles about building a business. raising money, hiring, firing, building out a sales team, operations, different contracts and negotiations. Entrepreneur.com is free and a great resource
  • Wired Magazine's article on Nick

Show Notes

Please note that I type these notes during the interview so there are likely to be misspellings, grammatical errors, and misquotes. This is not meant to be a verbatim account of our conversation, but a VERY basic text transcript of our discussion.

  • You joined the military later than most - what lead you to join the Marine Corps?
    • My career has been very non conventional. I didn't have a big picture plan when I was 21 or getting off active duty about startups. The idea of "living in beta" or testing hypothesis for your business and your life and career as quickly as possible
    • I was 26 years old when I commissioned in the Marine Corps. I had gone through OCS and was looking at either going into consulting, which most of my peers in business school were doing, or accepting a commisison. I thought long and hard about this before graduating from graduate school. It was hard because no one coming out of HBS had gone active duty since World War 2. When I asked people for advice they thought i was crazy for "throwing my life away." None of that feedback made sense to me. It wasn't until I talked to David Gurgain, who is a professor at the Kennedy School and a politial commentator on CNN, and he served in four different White Houses. Most importantly he went to Law School and then commissioned in the Navy after law school. he said "you should go do it and you'll never regret it." That's how I feel about itt. I was older than almost everyone in my platoon. But i saw it as a Now or Never proposition and knew I would regret it if I didn't answer the call.
  • What did you learn in your time in the Marines that has helped you as an entrepreneur?
    • I specialized as an Infantry Officer before going the Reserves side and serving iwth a few different companies all over the East Coast. In my Infantry training in the early days of getting the business off-the-ground was incredibly useful. Operating under ambiguity. Being able to preserve emotionally, psychologically and physically. We had a lot of challenges getting the business up and off the ground. Putting one foot in front of the others and having a big mission ahead of us. When yo're growing an organization it's important to make a mission crystal clear so that people can internalize it and get the big picture. So the day to dya may be a slog but you're getting out to work something bigger than yourself.
  • What aspects from the Marines did you most need to leave behind as an entrepreneur?
    • I've thought about this a lot.When you don't have a miltiary background it's easy to romanticize what goes on in the miltiary. The Marines has the best brand in the United States - they haven't missed their recruiting qouta in a long time because their brand is so strong. There are definitely live of martial life that do not extend into the world of entrepreneurship or starting your own business.
    • The biggest is dealing with beauracrcy. So much of the miltiary is waiting for the mission to come down. In startups, especially in the early days, it's all on you to figure out what th enext plan is, what the risks are, make those assessments, prioritize the entire world that is in front of you and develop an action plan. I tend to do best when there is no structure. Where it really is incumbent on me to develop and hold myself accountable and develop a plan. I do less well when given a plan and need to execute it. I was pretty happy to leave behind the beauraucy and think creatively and operate independently.
  • Between USMC & Plated?
    • Coming off active duty I didn't know waht I wanted to do with my life. I spent time Active Duty with the Marine Corps but was feeling a little lost. I was in my late twenties, had a fiance who had been working "Real jobs" and I hadn't yet had my first "real job" outside of the miltiary. I wasn't sure who I was supposed to be, what I was supposed to do. The thought of working 7am to 7pm in a job I didn't care about depressed me pretty fundamentaliy. I went to Wall Street for about six months and reinforced how different life paths could be. I saw my bosses on the desk on Wall Street who by all measures were successful - making a ton of money, had families, were running books of business - but many of them seemed to be lacking happiness, a bigger mission, and I knew that I didn't want to put my head down, grind it out, put up the periscope ten years later with  acareer I wasn't satsified with, beholding to a very large paycheck.
    • That's when I really started to look around and see that the world of startups exsited. This was 2011 so back a bit, when the fad for entrepreneruship hadn't really taken off like it has today. There weren't as many resources in New York i could go to and ask about what their path to building a successful multi-million dollar business was. I was able to team upw ith a business school friend of mine in New York - he had built a data storage company straight out of college (Josh Hicks, my co-founder at Plated). We did this Founder Dating thing for three months - figured out if we'd worked well together. We did volunteer work togetehr in Hataii for a couple of weeks and had been through some tought stuff together. I approached him as a mentor of sorts, and we figure d
  • How to vet a partner
    • There is so much that can and will go wrong - it's like developing a battle plan, everything looks great until it makes first contact with a customer. It's really improtant to decide - are you up for starting something on your own. Do you want a co-founder? If it's tough to ride the ups and downs alone, a co-founder is very helpful. If the answer is yes, it will be the most dillutive decision you make in terms of your equity. You're giving half the company away before the company even exists - so it's a ;big quesiton. But the way I've always thought of equity is you're going to reduce your total stake in the enterprise, but it's worth it to take that hit if you're increasing your probability of success by an equal or greater ratio. You're giving up 50% of business, but are you increasing probability of success by more than 50%? For me the answer was yes. I needed a co-founder, to go into battle together. The next question was who and what sort of skill set. It's a really important question - human nature is to work with people similar to us. Who talk and think the same way. It can actually hurt your probability of success, especially in the early days. So finding someone with complementary set of skills was important. It started with diagnosigin myself and fiding where I  was weak and strong, and where I want to spend my time, and where I want to complement this. That self examination is really crucial.
    • I knw I didn't want to do the coding or financila modeling. I wanted to be out selling and hustling. Developing the mission and vision and hiring employees and generating business. I needed someone who was more comfortable workign behidn the scenes, making sure the website worked, making sure we had the right spreadshets and wharehouse management point.
  • What was the genesis of Plated?
    • Josh and I had been working on a totally different idea and it wasn't working. It was going nowhere fast. We were working out of a friend's office and went for a walk in Central Park - a mile around, we would just do laps and laps talking and bouncing ideas off of each toehr. We came to this realization that this idea wasn't going to work. We knew we were going ot work together - we had been through months of intense work nto killing each other and actually liking it so we asked: what comes next.
    • We had been thinking through this meal kit concept for some time. On this walk around the resevoir at the end of a couple of miels of walking we turned to each other and said - this is what we need to do. This is what the next attempt at starting a business will be.
    • One was that food industyr trend in general. And out of personal need - our own experience
    • On the food industry side we had done hundreds of case studies in business school, but only one case remotely related to food - a cranberry manufacturing case. So we didn't really understand the size of the market, what they looke dlike, what the opportuniteis were, what the weaknesses were. As we explored that we realized (1) food is an ENORMOUS industry. Healthcare is bigger but incredibly regulated. While food is regulated it isn't nearly as tough to build a business as in healthcare. (2) as we looked across the landscape we realized that no one had built a large business in food with data. There had been big failures in the 90s and 2000's like WebVan - one of the first e-commerce companies, an online grocer who raised almost $1 Billion dollars from the best investors and now a case study as one of the worst failures. So fast forward from their failure to 2012 there really hadn't been data technology and innovation in a long time. It didn't make sense why that was the case.
    • The other realization for us was that we were both athletes - I'm an Iron Man Triathlete - it was hard, complex and expensive to get good food into our tummies. It took a lot of time to figure out what to eat, especially when it came to cooking. We found the more you cook the happier you are, the cleaner the food, the more control you have - this mattered to us in a big way. There was no way to make cooking to work for us, esepcially in NY  - the lines at stores can take an hour to get through. Working in Wall Street I put on 20lbs in six months, just sitting at my desk all the time and felt like crap. It was the first time I felt I lost control over what I was eating and what was going on in my life.
    • So between it bein ga huge market without a lot of data and technology and that problem we thought we could build a better food business with data and technology at the core DNA
  • For an active duty listener who is not familiar with Plated, how would you describe Plated to them?
    • We deliver everything you need to cook a chef designed meal at home in about thirty minutes. All the spices, meat, protein, kale, basil, plus a chef designed recipe card with an image of the final meal and some really easy to follow steps that anyone can use to get a good meal to your table in thirty minutes.
    • We've got over 15 options each week, the menu changes every week, our recipes change based on what you like and don't like and we deliver it directly to your door.
  • What has been the hardest moment since starting Plated?
    • We had a really tough time getting the business going. Five years out its easy to tell a success story, but the first year we ran into obstacles and a literal flood at every turn. First, Josh and I had been working on different ideas for six months prior to starting Plated. We had burned through our savings, our IRAs... we were out of money. it was go and raise money from other people, or go and get jobs, and neither of us wanted to do that. Which meant we had to raise money from outside investors on Day 0. Neither of us had done anything in food or e-commerce or building a consumer brand. You imagine we found people to pitch for our fledgling company and they would say - you've never done anythign remotely related to this! Why should we give you money!?! We quite literally had doors slammed our face. We talked to 200 people in three months and the only yes we got was from my dad, who was by no means wealthy. I grew up in a very privileged household where eduction was always first and foremost but he wasn't in a position to fund the business. He gave us enough money for ramen but it wasn't enough to get the business up and off the ground. It was incredibly humbling as we tried to convince people that we were going to accomplish this thing in the world but got rejected at every turn
    • Eventually we cobbled together some funds. I met this group of Angel Investors - people who fund very early stage businesses. They were former Israeli defense commandos. They had moved from Israel to Silicon Valley and had built two very succesful businesses and sold them for hundreds of million of dollars. They liked the Marine Corps story, our hunger and passion, and we raised our first money from those Angels. They took a big chunk of the business in exchange for the cash they put in - very dilutive, but we didn't have an option. Either stop our dream or keep going. So we had a little bit of money, but it didn't get easier from there.
    • I'm putting a book out later this year or early next year. I tell some more stories in there - The Evolved Eater - a quest to eat better, live better and change the world.
    • I tell the story of having a little bit of money to run the business, but we were working out of my apartment on my couch. I was going to the local grocery store and buying chicken by the pound and we'd pack it and hand deliver around Manhattan, really hustling. We realized we needed a professional fulfillment center if we were going to growth the business.
    • We looked all over NY for space that was refrigerated. We couldn't find anything. But we found a refrigerated cargo cater that they used to ship bulk goods across the ocean. We rented one of these things and parked it in Brooklyn that we rented on a month-to-month basis. This 40 foot long cargo crater we plugged into a 220V yellow cord the width of my fund and we started taking our inventory and run our operations from there right on the East River. Beautiful view of Manhattan right on the water. It was all fine and good until Hurricane Sandy hit in October 2012. It was also the date we officially launched as Plated. When Hurricane Sandy came down - it was really something to behold. The city shut down for DAYS! No electricity, elevators not working, traffic lights not working. It was like an apocalypse movie and it was the day we launched Plated - the worst day in the history of the internet. And then our cargo container got picked up in the storm surge and sucked out into the river. The only thing that kept our business from getting flooded out of business was that thumb width 220V electricity cord that got tangled around a phone pole and didn't get sucked out to sea. It was just a lesson in perseverance
  • Was there a point at which things changed - where you knew this was going to succeed?
    • It took a year of just grinding it out. Then we got some press - just through hustle, telling reporters our story, asking them out for coffee. That early coverage led to the folks from Shark Tank reaching out to us. We didn't apply, they reached out to us - the Producer said we love your story and think you'd be a great fit. They flew us out to LA in July of 2013 - one year after we officially incorporated we were at the Sony lot filming for Shark Tank. We filmed thought it went well - didn't hear anything from eight months! Now we're starting to get nervous because the whole idea was to raise money but also the publicity of getting in front of 10 million households on a Friday night.
    • To make al ong story short, we got a call an producers gave us one week that the show was going to air. We were two years in business and not seeing any breakaway velocity. A few hundred orders a week, just grinding things out. Then our Shark Tank episode aired and it was an inflection point - we had sprinted to get a nation-wide system in place. We wanted to take advatnage of the nation-weid media. We saw 1000X increase in traffic to our website - even with all our planning, th esite still crashed. It was great. We saw more revenue th emonth following the airing than we had seen in the entire history of the business leading up to that point. That coverage and demand it generated validated that this is not just an idea that works ro in San Francisco - this appeals to folks all over the country in every zip code. That gave us the confidence to raise our first "real" money - our Series A, which was $15 million. It also validated that we could go then build TV advertising and investing to really grow the business faster. It wasn't until two years into the business that we had that validation
  • What advice do you have for someone on active duty who is thinking of starting a company when they get out?
    • It might be hypocritical advice, but it's a really hard transition, going from the military straight into a startup lifestyle. Goign from having a persribed routine of what to wear and eat and then having complete and total freedom over everythign you do. It can be completely overwhelming. The advice I would give is - if at all possible, go try and work at a startup (fi you want to be an entrepreneur) at another startup for 3 months, 6 months, a year. See how startups succeed or fail and try to learn on someone else's dollar before hussling on your own. There's no susbtitute for doing it yourself, but there's SO much to learn and it is so incredibly hard that you want to give yourself as many advantages as possible. If you can find a team taht will give you a shot - that you can learn how young businesses operate, what financials look like, what building out a team means, what hiring and firing means in the private sector, getting those skills and expereinces - it'll be invaluable when you go out on your own
  • What resources have been helpful to you - books, podcasts, classes, etc - that you would recommend to other veterans thinking of starting a company?
    • There's a great book by Ben Horowitz at Andreesen Horowitz - the hard Thing About Hard Things. Before becoming a VC, he was an entrepreneur and started a few businesses. He talks through his experience and takeaways for aspiring entreprenerus.
    • A resource I go back ot again is entrepreneur.com - you have to sift through some of the news, but there are a lot of great articles about building a business. raising money, hiring, firing, building out a sales team, operatinos, different contracts and negotiations. Entrepreneur.com is free and a great resource
  • Final words of wisdom?
    • Whether you go or build a business on your own or join a team that is already operating, there is such a hunger out there for veterans. Especially post 9/11 veterans. Everyone is looking to hire vets both for waht they can bring to the table and it's also a great story to tell to everyone. There can be challenges in translating what it means to how you can help build or run a busines,s but don't give up if at first it's a challenge
Aug 9, 2017

"Wouldn't it be great if our country didn't have to care about Iraq's oil, or the Middle East's oil? Maybe we should start an energy related business - ok let's go figure that out. That was roughly the thought process that gave us the left and right limits of starting an energy business. That started a process where we just endlessly turned over rock, after rock, after rock trying to find something, while absolutely not knowing what we were doing. Then we eventually stumbled across something where people would pay us money for it. So we just said let's do more of this thing and do it in as many spots as possible.  "
- Chris Boggiano

Jon Boggiano and Chris Boggiano are the Co-Founders of Versame, which leverages technology for large scale impact to improve early childhood education and language development. Versame has raised $2.5M in funding and is a team of sixteen.

Jon started out at West Point, after which he served for five years in the Army, most recently as an Operations Officer & Battle Captain, 1st Infantry Division. After his transition from the Army he worked at Carrier Corporation for three years, before starting his first company, Everblue. Jon is a Sloan fellow from Stanford University.

Chris started out at West Point, after which he served in the Army for five years, most recently as Operations Officer, 7th Army Joint Multinational Training Command. He worked at Tessera for one year prior to starting his first company, Everblue. Chris is also a Sloan fellow from Stanford University.

I came across Jon and Chris in a 2016 Forbes Article about the Top 25 Veteran Founded Startups in America.

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Selected Resources

Show Notes

Please note that I type these notes during the interview so there are likely to be misspellings, grammatical errors, and misquotes. This is not meant to be a verbatim account of our conversation, but a VERY basic text transcript of our discussion.

  • You each separated about two years apart from the Army - what lead  you each to decide to transition from the Army?
    • Jon: Older than Chris, so transitioned first. Was fortunate that he started just before 2011. Got to experience Army before and after transition. Post-9/11 Army was much more innovative. It shook off the beauracratic shackles. I was stationed in Germany for over five years; it was great but intense. Between training and deployments was gone for most of that five years. As I started thinking about having kids, the future looked like back-to-back deployments with training in between. At that point decided I as going to get out - if I was going to do it, I wanted to have a plan and attacked getting out spending 1.5 - 2 years getting out. Still in the Reserves, but mainly got out for the op tempo
    • Chris: Combination of op tempo. 9/11 happened my senior year so I graduated into an Army at war. I was deployed back-to-back - same decisions of not knowing if and when it would end. Uncertainty was a big factor. For better or worse what was most interesting assignments was early on in career was fortunate to do a lot of interesting things. The nature of the beuaracacy was part of it too - the Army functions amazingly, even in the best of times, it's limited in its ability to innovate.
    • Jon: One thing i was looking for was a better meritocracy. Early on in the Army everyone got promoted at the same time and the same assignments. There were small differences, but for the most part there wasn't differentiation between good and bad officers.
  • What was your first job search like, and what advice would you have for veterans about their transition?
    • Chris: it's impossible to know what it's like on the other side until you get there. The thing I didn't expect was that in the Army there was this binary expectation: career or getting out. When I left the Army the company I went to thought I'd be there for a very long time (decade long). One year later I was leaving to start my own company. Going out with the expetation of doing the best you can and if you move on that's ok. I had a lot of guilt when I left that first company. For better or worse it wasn't the right fit and taught me what I don't enjoy and lead to Jon and I starting our own company together. In the long-0term it worked out but in the short-term there was a lot of stress.
    • Jon: For me a lot of my preparation was reading books, and going through the Cameron Brooks program. Talked to 25 people who made the transition ahead of me and gegtting their advice. SOme of that advice was to make a list of personal goals and values, and dust that off around tax season. Make sure I'm following that and staying true to it. I didn't just want a job - I loved the work hard play hard mentality of hte Army. I didn't just want a job I wanted great people.
  • How did you two start to work together?
    • Chris: OUr dad was a cop and mom was in education so entrepreneruship wasn't in our head. We hadn't thought a lot about it. We had worked together throughout school at West Point and would work together. We were in the same Brigade and deployed twice together in the same unit - we were workign together pretty closely in the military. I moved to Charlotte, NC because Jon was located here. We had worked together in the past, and when we took the plunge to startups it was a natural transition to work together in that capacity. The startup piece was the bigger of the two.
    • Jon: when Chris moved to Charlotte, our dad was always doing business things on the side. He was always a community activist, so we didn't start out wanting to be entrpereneurs but just looking at small scale business ideas. Two events stand out. I got out and enjoyed my job and we made a concious decision to become entreprenerus. Chris, day one, came back and said 'this is not what I want to be doing' If his experience had been different may not have started a company together. That started the idea of the week phase.
    • I had done really well at Carrier doing sales, and my boss left to go to another company. Ultimately led to the decision - are we going to be entrepreneurs.
  • Was your work experience prior to startups helpful?
    • Jon: For me it was, at Carrier. You just gotta get one thing to work in one area and you can scale it. Understanding finances, which I never dealt with in the Army. It's not you can't learn these things, but having had the big corproate expereince made it clear I didn't want to do this, and gave me some training that helped in my startup. It made my decision all the clearer - I can't imagine going back to cubicle now. Not having had had that it would have made that option seem more appealing
    • Chris: The transition I did in short order, but I did make a transition from the Army to civilian world, and then to startups. I'm glad they were staggered. As much as the company I went to knew i wouldn't last there, do think it was hlepful. It gave me time to build an identity and make the transition. It allowed me to separate the two parts of who I was, and then in an intentional manner make the leap to an entrepreneur. It would be more painful and risker for me to jump from one into the other.
    • Jon: We joke about this all the time with recent veterans; my wife calls it "command voice". You have to stop using acronyms, stop cursing, understanding business acronyms. I read a slew of books and that helped with the transition but it takes time to desensitize and be able to relate to civilians. you need to plan for a transition period. There's teh identity piece of not having the team. It took a few years to form a community. In Europe on the miltiary base we all did everything together. We had a forced commiunity in the military. In the civilian world you may have nothing in common with your neighboars.
  • How did you choose to start a company?
    • Chris: for me it was a process of elimination. I looked at 'what am I going to do in my life' most of my peers went to grad school, work at a big corporation, or work for other federal agencies. these were the three main routes - I didn't think I wanted to do any of those. I didn't want to go abck in the Army. I can't tell whether I changed or the world changed - I didn't know ANY startup language when I started this. I didn't know about VC, revenue, etc. So it was a process of elimination, getting out mypersonality I had a more of a chip on my shoulder and more committed to going after it. The biggest thing the military helped me with was that working for something I cared about - 'we're in Iraq... I wish we weren't here. We probably wouldn't care if there weren't oil. Wouldn't it be great if we didn't have to rely on energy. Let's start an energy company' That was roughly the point of starting our first company, and then endleslly turned over rock, after rock after rock. It's hard to overstate how little we knew but being motivated to figure problems out as they came to use.
    • Jon: My advice for anyone transitiong is to be deliberate. The people in the military are usually drivers - so be deliberate. The business world for me was still very restrictive. I wanted to control my own destiny. I wanted to choose when I take vacation, that's why I left the mlitary. I like building things and making things - I like creating things. I wanted to have more ownership about it. I also wanted a bigger purpose. All of our companies have been social mission companies - wanting to make the world a better place. We were sitting down on a Thursday evening - are we going to do the startup thing.
  • What was the Everblue experience?
    • Jon: we ended up selling it after about four years. We chose a problem we wanted to focus on and then from there we did a "movement to contact" - develop the intelligence around the enemy. We talked to every expert we could, and in that process became knoweldable experts. That took about two years. IN that process became experts. People said 'if you could solve this porblem, we'd pay you' but without those two years of turning over rocks... we wouldn't have foudn it. I don't think it's about the idea - it's about the idea you're solving. If it was obvious the problem you're trying to solve it would already.
  • How did you make money?
    • Jon: We did a lot of the research while at other companies. Chris gets the credit - he jumped off his job and started full time. Anyone in the military if I said in the next year you need to replace your salary, I think anyone in the military can do that. I give Chris credit for tdoing that because he did it first.
    • Chris: For me it was really scary to think about taking that leap. the exercise that was most helpful to me. I got out of the Army and bought a house and the mortgage rates were higher then than now. My wife had a lot of student loan debt - financially even being in the corporate sector I had so many expenses - gym membership, laundry, etc. There's this fear of - what can I do if I don't pay the bills. What liberated me was: what happens if I don't pay the bills. It was just my wife and I at the time. She had just graduated from grad school. The day I quit, she was working at B&N for $8 / hr, so household income was $20k per year. We had all these bills, and I thought what happens if we burn through savings and the bank takes my house... we'd move in with our parents and go get a job again and figure it out. We have a family and support network to get through it. It wouldn't be pleasant, but compared to things I saw in the Army, it's not that scary. We thought we'd do energy audits on homes when we started out. We had lined up thousands of homes of work. Along the way we got training on this. Jon threw up on Google Adwords a one page website that offered training. People started to call to ask for training - then we shifted to a training business that over the next year or two we grew to 100 or so locations.
    • Jon: The biggest risk in a startup is trying to do too many things.
  • Stanford Sloan
    • Chris: I didn't want to go to graduate school. Jon nagged me and we applied together. I had a ten day window to get my application together and we applied together. It was the most flippant application ever. I was pretty truthful about why I considered this. When we interviewed they asked what happens if we only accept one of you. I said, both or neither of us. I'm very glad we went there - that's where Versame came from. Jon is potentially more thoughtful than me and it balances out my riskiness
    • Jon: Even though we had an epic success we were intent on starting another company. We still felt like amatuers. We had never had any formal business training. So I wanted to address our weaknesses. Second, we had just made a lot of money and Stanford was an adventure. It was the reward for having had the success of Everblue. It was a nice break a one year program. It was the experience of doing something different. I had moved seven times in three years. I was feeling th eitch to do something new.
  • What was the genesis of Versame?
    • Jon: When we had Everblue, we straddled education and energy. When we sold Everblue we had expertise in two domains. When we went to Stanford we decided to go deeper into one of them. Energy was making a lot of progress. It was really taking off and it still is. It's a national security issue. When it came to educaiton we struggeld with the technoloyg and the people we were training. It felt like the impact we coul dhave on people was much greater. If it was an innovation that involved technolgy - we turned over every rock. We were about to walk away - it's an in person business. There was nothing moving the needle at the time. Then Chris read an article in the NYT about an infant training lab at Stanford. She was so excited someone was taking an interest in her work - ifyou really need to impact life outcomes you need to start at birth and do it before kindergarten
  • How would you explain Versame to someone on Active Duty?
    • Jon: We're envisioning reimagingin education. not education at a classroom but at home. We're giving parents the tools and helping them apply the research to grow happy succesful children. We'll help you do that through the technology and tools to do that. But you need to start at birth.
  • What was the first year like starting Versame?
  • What has been the biggest challenge so far?
    • Jon: Biggest change in perspective is that the people in need of help is the agencies in the medical industry. The tools we build help teachers, nurses, therapists - the people who are caregivers. We're trying to change a mindset - most poeple are worried about safety but not about brain development. They don't think about education until kindergarten or preschoool. There are some subculttures that believe this, but we want the mindset change across America.
    • Chris: your memory of childhood is spotty. Many people think you're as smart as you are and you were born that way. YOu don't remember your parents teaching you and hleping you. People attribute intelligence to genetics rather than environmental factors. Research suggests parents can have a MASSIVE impact on their child's success in life.
  • Starting a business with family
    • Chris: research says that more likely you'll fail; it's harder to have tough conversations with family members. Little problems become big ones. The most improtant thing is that you should have a business partner - it's more fun. You should be able to have a good fight and get over it. We fight all the time but it never sticks. There's not a grudge - we can have our disagreements and it's not a big deal. If I wasn't in business with my brother this is the qulaity I would want with someone else.
    • Jon: I would add that whether siblings or others, the most important ingredient is the partners and the suppor tnetwork. I think it's essential to have partners - your energy level and momentum it helps carry you. If all the stress is on one person's shoulders
    • Chris: a lot of ivnerstors won't invest in solo founders. IF yo uhave someone else to pull you through you're more likely to stick it out. From a statistiacal stnadpoint most buisnesses are successful with two or three partners. It's more fun when you have more people to be together.
    • Jon: Defense Secretary Mattis says leaders need to be learners. I think this is true no matter what you're doing. We knew nothign about hardware but we attacked that. We've done well with that - we're the ifrst to ship a product in our Stanford cohort, you have to attack what you don't know. Yo8 uneed to ask for help and advie. That's tough for veterans. I've gotten over that - you gotta ask for help, and people are more than happy to share it.
  • Resources
    • GOOGLE!
    • Jon: it's the best form of online learning. Career advice books are great. If you're a big believer in the mission of the miltiary you'll learn how improtant business is to the strength of our nation. Our economy and the businesses we build enable us to pay for a good military. Business is part of the life time of service. Read books that frame business in the sense of innovation. I'm loving Elon Musk's biography.
    • Jon: I always ahd this mindset with EverBlue that everything will be better in three months. But I've always felt on the cliff's edge... I've learned to live with this fact and realize this is normal. that fear of failure never goes away. Just accept it. Dealing with a team, there's always some personal issue. I thought if I solved one issue my team would be perfect. I know realize this is the core of my job- keeping my team performing. These are two norms taht never chagne. You'll never feel successful, you'll always have the same stress
Aug 2, 2017

"There was a point in time that we had $719 left in the bank. There were late night discussions sitting around the table and talking about what we're going to do; how we're going to inform people that they don't have jobs. How we're going to inform our larger investors that we ran out of money and we're not going to make it. And we turned that around in the middle of the night with one particular investor who became of strategic importance and that was in the same year that we were acquired."
- John Gossart

John Gossart is the Cofounder and Chief Operating Officer of GoodWorld (www.GoodWorld.me), the FinTech startup revolutionizing philanthropy and social payments.  GoodWorld was named one of Fast Company’s Most Innovative Companies of 2016 and D.C.’s Best Technology Startup. Prior to GoodWorld, John was an original partner at RideScout (www.RideScout.com), the tech startup acquired by Daimler-Mercedes in 2014.

Before becoming an entrepreneur, John served over 22 years in the U.S. Army and Government, work that took him to various locations across Africa, Pakistan, Yemen, Afghanistan, Iraq and Europe, most recently serving as a deputy director of special operations and counterterrorism policy in the Office of the Secretary of Defense.

He graduated from Boston College and has a Masters in Public Policy and Fiscal Management from the McCourt School of Public Policy at Georgetown University, where continues to teach policy and economics as an adjunct professor.

John’s indie rock band StoneDriver (www.stonedriver.com) recently released their first studio album "Rocks" and in between GoodWorld, teaching, and shows he lives a quiet life in Old Town Alexandria, Virginia with his wife, Lisa, and their four sons.

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Selected Resources

  • The article where I found John in Forbes can be viewed here - https://www.forbes.com/sites/marklrockefeller/2016/11/11/the-top-25-veteran-startups-in-america/#5120ea756e84, The Top 25 Veteran-Founded Startups In America

Show Notes

Please note that I type these notes during the interview so there are likely to be misspellings, grammatical errors, and misquotes. This is not meant to be a verbatim account of our conversation, but a VERY basic text transcript of our discussion.

  • How to explain Good World
    • Trying to solve the problem of friction-less payment experience. In the charitble giving spac eright now. Allow make people to make donation to causes with just a hashtag or tweet. They have 3k charity partners - save the children, PETA, green peace, salvation army, etc - when they post o nsocial media if you tweet back with # donate, his technology kicks in, processes that donation through a CC transaction and adds it to the charity. You get a response on social networks
    • Working with charity right now but talking to companies about how this might apply in other locations - donations to colleges, commerce, political donations
  • After 22 years of service in the Army, what was your first civilian job search like?
    • Not help on inspiration or advice - it was happenstence
    • Was in Yemen with three people he tuaght with at West Point - they reached out because they had an idea for a transportation technology startup and were looking for a guy to help with revenue and finance
    • They reached out and he was in a military mindset - he didn't even answer the first time they reached out. He didnt' know about apps or startups. Ignored it, a few months later when he was in Pakistan, after they launched at SXSW he was in a different spot - hadn't been home much in the last ten years, his sons were in high school and college - he was looking for a change.
    • He made a hasty decision and decided to join. He was really tired too from the military. Took steps to get out, thought he'd work with them for 6 months and wouldhave time to figure out what he wanted to do next
    • Two things happened ^6:30
    • (1) The adrenaline rush he liked in th emilitary abounds in the startup world
    • (2) They didn't fail - two years later they were acquired. both financially and personally and professionally it was a life changing experience.
  • luck is a residue of skill
  • What skills did you carry from the military and have to develop in your first startup?
    • There were certainly attributes and skills and perspective that you pick up in mltairy service that are unique to military service and are helpful in the buisness world or specificially the tech startup
    • There are more things that yuo need to leave behind
    • They maybe served you well in the military, but they won't serve you well outside
    • At the beginning, a co-founder would come to his dining room table at 6:30am (their office) and they would open up their personal laptops and start trying to figure out what to do
    • The idea they had was huge and inspiring... but what they were supposed to do, he had no idea and felt in above his head
    • As they started working the business development side of things he was frustrated that he didn't get a response in 24 hours. But the world odesn't work like this - you'll get a response 3 weeks later as if they still got it. THe heirarchy and protocal that are second nature in the military you need ot leave behind - they odn't work well in flat, dynamic, tech startups. Working with engineers is unique and takes skill as a leader to collaborate with them
    • Respect - everyone on the other side of the table. Always giving them the benefit of the doubt. Checklist mentality - people make fun of him, but its VERY helpful to them as a company. These are the things we need to get done before we go live with this new feautre or this new product line.
    • Preparation - the premium placed on preparation in the military before executing.
  • What was RideScout journey like?
    • Their CEO was always consistent on this is going to be a incredible company
    • The four co-founders were all coming from differnet skill sets
    • Joseph (CEO) was th evision guy and the evangelist - always larger than life - on stage and in the elevator
    • John was rolling up sleeves and trying to figure out how to create sustainable revenue
    • John had his down a lot and could have head up more. Jospeh always had his head up and he had to fight to get him to look at the details
    • It happened very quikcly - talking to some entities about raising a few million dollars from firends, family and angels Trying to raise an institutional insittuion, when Dymler came in we thought they were goign to lead our Series A financing. Instead they were looking to acquire them from the start.
    • At this point had 15-16 people (some part time) when they started talking about an acquisition
    • Then went to 50+ employees after acquisition
  • What was the origin story for GoodWorld?
    • They launched RideScout out of incubator called 1776 in DC. In the course of launching the company there and working there and growing their team, he came to know other entrepeneurs in the building
    • one was Dale - his co-founder. It was her idea and she's the FOunder & CEO
    • She had a great idea, an intern, and a laptop, and an engineer collaborator
    • She didn't have any corporate sturcutre. He was advising her on how to take it to the next step. He is the COO and CFO hats
    • The more he came to know Dale, the more he learned about the idea and he thought about the possibilities in this space. It was cool to go to market in philanthropy. Jesuit educated and he always though philahthpoy would be what he'd have to do on the side, but this was the opportunity for his day job to help causes he cared about
    • he found himself thinking about this at night and coming up with ideas with Dale as they were being acquired
    • By the time they were acquired in 2014 he was neck deep in teh acuisition. Then they had a HUGE budget and needed to get going with it. In the course of this he helped her raise the firstbit of money and the light went off. They raised $500k in days. It struck me that people this really resonated
    • 19:00 raised $500k in days
    • Ended up raising $1.6M in their first seed round with instituational finace people as leads
    • While this was unfolding ti became clear - if I'm going to do this I need to committ to it. How could I make the transition without leaving too much money on the table at RideScout.
    • he negotiated a deal to phase himself out and still retain big parts of his equity
    • I was making a lot of money at Dymler - but I would have been a subpar executive and subpar co-founder
    • The idea was too big to pass up -wasn't financially smart in the short term but my passion was with GoodWorld
  • Co-Founders
    • joseph came up with idea, Craig was already out and put in some money. He was a second time entreperneur, and had already started a company that had exited. Joseph had the big idea while on active duty, Steve was just getting out of the military (22 years) and he was the last one to join the core team - during the transition he was workign with them. Everyone was a veteran, but they were in different points of serve
    • If you're starting your own thing, there are two things that are easy to give and hard to take away: titles and equity
    • if you're going to make someone the co-founder
    • When you incoporate, one-time you can give founder shares by the IRS. these are the best shares to have and yuo can only do this once. You shouldn't enter into calling someone co-founder or anythign with a c (CEO, CFO, COO, etc) - if you lack business and instituional expertise you can bring them in and if they don't stay it doesn't vest and then you don't get stuck with themif they don't stay with the company
    • Sometimes people want to find an engineer to make CTO and co-founder. Maybe you need ot just find an engineer - try them out and you can make them CTO later on, but don't jump into it
  • What advice do you have for veterans aspiring to entrepreneurship?
    • Don't believe your own press - this is more true for transitioning veterans today than ever before.
    • My accomplishments look good on paper - there are MANY people around me  who he considers WAY more accomplished than him.
    • 28:23
    • For veterans transitioning now we are in such a divise point in political scene. The narrative that both side want to cling to - which is popular with people - is this big narrative of how much we owe to vetarans for servie. I don't disagree with this - I'm very grateful to everyone in uniform who is protecting me and my way of life and allows me to do what I do. I'm very thankful for this.
    • Btu this has become conflated with another narrative -t hat veterans are OWED other things. Financial fudning for thier startup - what if it's not a good idea? What if they're not a good entreprenuer? Just because he's a veteran doesn't mean you should invest in their company
    • I worry we're building our soldiers iwth a sense of entitelement that there is an expectation that when they step out in the civilian word they are owed soemething
    • For me I'd argue I got more out the Army than they got out of me. We were 100% square when we got out of the miltiary. They gave me the best leadership experience possible in incredily high intensity sitautions. I have not one complaint about the ledget between me and the Army. And I'm still getting paid a pension and some disablity
    • To walk out and think I'm entitled to somethign because I'm a veteran
    • I don't want to be entiteld to funding because I'm a veteran, but because it's a good idea, and people think I can do this
    • If it comes down to me and the guy next to me there may be attribtues that are particualr to beeing a veteran that give me an edge
    • Today I start the converstion that I'm an entrepreneur - not tha tI'm a veteran. Oh by the way I'm a veteran
    • I get the sense that there are a lot of people who think everyone is a hero and is entitled to something
    • I've been out for a while and I do see people who are treading water
    • The best way to get a step up is the fundamentals - if yo have a real solution to a real problem and a good team and product - cahnce are you'll be succesful. Veteran piece may help you at the margins. But without the fundamentals it doesn't matter
    • 34:43 - 35:16
    • there was a period when we had $740 left in the bank - how would we tell people they don't have a job. how do we tell investors - we turned it around in the middle of the night with one investor.
    • you need ot be prepared for this - it might not work it. The market is VERY efficient - you need to listen to it. It's not just about starting new things - when you get out of the military and work for a normal company and you turn to your boss and say I've got a dentist appointment today - they say, that's not my problem you need ot be at work. We learned in the military you gotta let me go ebcause I've got a dentist's appointment.
    • As a veteran - you were given a lot of what you were owed - thanks of grateful nation competitive paycheck etc. it comes down to fundamentals - if you
  • How would you describe your role as COO & CFO?
    • One of the reasons he got the bug when he started in startups is because it reminded me a lot of my scrappy days as chief of staff at brigade or exeuctive officer or operations officer. YOu never had the same day twice. I like taht. you're moving from crisis to crisis or executing quickly with little resources, problem sovling, etc. I loved this in the miltiary and I ahd some jobs in the miltiayr that were'nt high paced and i quickly sought the next thing because it wasn't fulfilling. The COO role in a startup is you never know what the day is going to bring. There are a lot of things in the day you didn't know yhou were goin gto have to face when the day started
    • you'll hvae to call people in and fire them and search for people to hire - you're looking to model out their expenses and burn to see to the day when they'll run out of money. i want this date burned into th eminds of everyoen in teh organiztaion. The way we change this is bygetting more money or more partnerships or more funding
    • I don't have a normal day - i go to NY and SF asking epople for money, negotiating with strategic partners I want to brin gon. I look half my time looking inward and making sure trains are going to run on time.
  • What resources have you found helpful that you would recommend to other veterans?
    • I don't have a great answer
    • I was never good at reading the seminal biography of military leaders
    • The pro dev reading list that followed me around in my career that everyone was reading... I was not drawn to those things
    • When I got out there are always startup books that are hot that everyone is reading
    • Reading is critical - you shouldn't take a meeting without learning everything you can about the person across the table
  • Final words of wisdom?
    • When we were acquired I felt very conflicted and wanted to hang out. You need to commit to what you're doing. I see a lot of people who fancy themselves vetraprenerus. They don't want to take their hand off their paycheck or that comfortable thing. There is an opportunity ocst for 8 hours a day doin gsomethign else. It'll make you less likely to succeed in something else
    • If everyone could start something huge on the side and not leave your day job until it was huge, everyone would do it
    • If where you want to be is starting something new, you need to committ to that. There should be risk, there shoul dbe people who think yo're crazy, and you should be a little anxious and a little scared
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