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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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 (, 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 (, 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 ( 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.

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

Selected Resources

  • The article where I found John in Forbes can be viewed here -, 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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