One Year Later: What I’ve Learned & What’s Next

Ray Crowell
humble words
Published in
4 min readJul 18, 2016

Holy sh*t! What a journey! It’s hard to believe it was little over a year ago that my dear friend Sean Maday offered me the opportunity to get involved with the veteran and military spouse-led tech startups in his organization, Patriot Boot Camp presented by Techstars. Not only was I physically employed across the country, but the bulk of what could be considered my “entrepreneurial experience” was working within scaling nonprofits — hardly a candidate to engage with high growth, innovating technology companies. But as luck (read: opportunity and hard work) would have it, it turns out my successful-albeit-schizophrenic career path shepherding the people who spearhead organizational change is actually of great value to growing for-profit businesses. It helps, too, that I’ve truly found my passion working with these humans.

During one of the Patriot Boot Camp weekends, I was introduced to the Founder & CEO of Bunker Labs, Todd Connor. At the time, Bunker Labs was a grassroots organization expanding nationally with a grand mission to “catalyze the entrepreneurial potential of military experience to lead the American economy.” Todd and several others encouraged me to get involved with the Bunker which had just popped up in my backyard, led by Emily McMahan. What ensued was an amazing (so amazing I actually quit my “real” job) initial four-month period of discovery which I chronicled in my LinkedIn posts “Why Bunker Labs DC,” “The Value of Bunker Labs DC,” and “Solving Problems” … And then the real work began.

I was humbled and excited to take the reins for the Spring 2016 cohort and even more so to work with such an outstanding team. Harry Alford and Mary Iafelice, if you don’t know them, are the Managing Directors at BLDC, and are seriously hardworking, fast learning, and fun loving. Together, we put in grueling weeks, tireless personalized effort, and always kept a “beginner’s mind” to never lose sight of ourselves as a ‘startup leading startups’. That being said, I’ve come to understand a few things by pushing two classes through our pilot accelerator cohort.

If entrepreneurship as a “career path” is interesting and not compelling, it’s not for you. There is a great deal of focus on the post-9/11 transitioning military veteran (~250,000 annually), and their opportunities to be the “Next Greatest Generation.” After doing some more number crunching by way of my signature “Alabama Public School Math,” the rough number of veterans from that 250,000 each year who have a fighting chance to build a high growth startup is 62 (i.e. the one-tenth of one percent). The rally cry for entrepreneurship is not necessarily a bad thing, but let’s be sure that we are putting in the disciplined legwork before investing any capital (financial or otherwise) in the pursuit of entrepreneurship. Speaking of disciplined legwork…

There is no replacement for the value of raw experience and on the job scar tissue. One of the best pieces of advice I can give would-be entrepreneurs before they begin down that road is go work in a startup first. For military veterans especially, there are more opportunities to get hands on with high growth tech companies than ever, and I would urge those who are transitioning to work in a startup, start generating income, and then launch. Getting first-hand knowledge of the differences in risk assessment, daily pace, cash flow, and management styles by digging in with others and then venturing out adds a level maturity for first time founders that is essential. The central thing I want to express is that the best source of learning is by doing. If you’ve only been immersed in a startup by way of literature or “shark tank” — that’s not good enough. If and when you’re looking to raise outside capital, your investors will care about your experience, not who you’ve been following on twitter.

Work with people who convert feedback into action. One of the hallmarks of a more mature, seasoned founder is the capacity to “check the ego at the door.” Entrepreneurs who are coachable, systems thinkers who actively seek insight across markets and disciplines and apply a test-and-learn approach to their business are guaranteed success. We evaluate against this profile when we validate who we work with. There is great mutual satisfaction, shared learning, and increased chances of success when working with humble people.

Becoming humble ventures. These are all lessons I’ve taken to heart. These last six months, I’ve been hustling 80 hours weeks, listening, learning, iterating, and finding those humans I’m confident can execute on vision. This week, I conclude my tenure as the Executive Director of Bunker Labs DC, and am proud to announce mine and my staff’s merger with humble ventures. Led by Ajit Verghese and Kayode Owens, humble ventures is a micro-VC firm that believes the best way to realize opportunity is through cooperation, partnerships, and pilots between startups and established organizations. We are more energized than ever to launch and deliver an acceleration lab for startups in partnership with the Alexandria Economic Development Partnership, Capitol Post, and Bunker Labs DC — folding in a co-operative of private sector, academia, government, and investment leaders.

How fast a startup converts feedback into action is what matters most, and our team is here to do just that.

You can find us at humble.vc and on twitter @humbleventures.

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Ray Crowell
humble words

Exiled Alabamian | Venture @SCAD | Builder-at-Large @humbleventures | Former Fellow @harvard | Veteran @USAF #getshitdone