Geek of the Week

Geek of the Week: How lifelong entrepreneur Bob Crimmins’ little poker sport ballooned to a 2,300-person startup group

Bob Crimmins with his daughters on the day they met their Kickstarter goal for the ‘Wise Walker.’

There are plenty of stories of entrepreneurs who got their start in dorm rooms and garages, but how many can trace their startup hustle back to the playground?

At 12-years-old, Bob Crimmins began his education in entrepreneurship by upselling lollipops from 7-Eleven to his classmates, learning a valuable lesson in demand-based pricing. As a kid, Crimmins also worked for his family’s businesses and went door-to-door selling custom glasswork he made.

Entrepreneurship and innovation often go hand-and-hand, and Crimmins was no exception.

“I wrote my first program on punch cards in 1978, a time when it was neither cool nor lucrative to be a 15-year-old programmer,” he said.

Crimmins founded his first tech startup in 1999 and went on to launch four more after that. Along the way, he started a poker game for friends in the startup community. That was back in 2006. Fast-forward to 2019 and what began as a casual gathering has grown into Startup Haven, a community for entrepreneurs with chapters in six cities and 2,300 members.

Up until now, Crimmins estimates he dedicated about 15 percent of his time to Startup Haven. This year he decided to make it his full-time gig so he can continue to scale the organization. He plans to expand Startup Haven to three additional cities in 2019 and 10 in 2020.

Members must qualify as “venture-scale” founders before they are accepted into Startup Haven. In addition to regular poker games, the group hosts founder dinners and other events each month.

Crimmins still makes time for the occasional side hustle, like Project Wise Walker, a startup he founded with his daughters. Together they designed a clip-on carrying case for dog owners to stash smelly poop bags on walks.

Related: These 11-year-old twins and their dad just launched a Kickstarter for an innovative dog poop bag

“The most rewarding experience I’ve ever had as an entrepreneur and as a father was teaching my twin daughters about entrepreneurship by actually co-founding a company with them,” he said.

We caught up with Crimmins for this Geek of the Week. Learn more about his journey and Startup Haven below.

What do you do, and why do you do it? In 2006, I started asking folks I knew if they wanted to learn how to play poker. Since virtually everyone I knew at the time was a startup founder, exec or investor, that’s who joined in. Learning the game was fun but what fascinated me was the relationships that were formed by the folks around the table. Seeing the impact of those relationships was amazing and it inspired me to keep the game going and growing. Fast forward a dozen years and that humble monthly card game took on a life of its own and became what is now Startup Haven, a founder support community with more than 2,300 founder, exec and investor members in six cities.

We still host that fun, invite-only, low-stakes poker event every month in all six of our chapter cities (we have hosted more 300 Startup Poker 2.0 events so far)! But if you’re not a Startup Haven member then the reasons we play poker are probably not what you think. I have written extensively about why I think every startup founder should learn and play poker. If you’re a full time, venture-scale founder or an active startup investor, you might find it interesting.

Over the years, Startup Haven has become much more than just a poker event. We have hosted hundreds of Founders Dinner events, dozens of special educational events. Beginning in 2019, scaling Startup Haven’s impact has became my full-time focus and over the past few months, we have launched a members-only recruiting program, an accelerator program and an investor matching program. Startup Haven started a personal passion project and it will always remain that. But scaling requires a different mindset and that makes it feel like a startup. It’s an exciting time.

What’s the single most important thing people should know about your field? My “field” these days is helping founders succeed more by failing less. Startups fail so often that it’s a wonder why everyone hasn’t just stopped trying. A “Top 10” list of the reasons why startups fail would include a hundred reasons. This stuff is hard and there is no silver bullet, but I have come to believe that relationships and cogency are the two best hedges against failure. I’ll buy dinner for the first person to convince me otherwise. These principles are precisely what motivated me to keep Startup Haven going for all these years and it’s why I’m genuinely excited about the new GroundWork accelerator.

Where do you find your inspiration? My daughters. Humble founders. The magnitude of human experience.

What’s the one piece of technology you couldn’t live without, and why? CNC lasers. I reckon I use mine three to four days a week — there’s always something to make, to fix, to experiment with. Growing Startup Haven has made that more difficult lately but it’s always on my mind and if it’s been more than a week since I’ve had the opportunity then I really miss it.

What’s your workspace like, and why does it work for you? I’m a nomad. I work out of a backpack. As a community organizer and a mentor, I spend time at a variety of co-working spaces around town. I’m currently working primarily out of Thinkspace, which I love.

Crimmins at the Columbia Tower Club, where he often works.

Your best tip or trick for managing everyday work and life. Everyone in the startup world is perpetually overcommitted. So protecting your calendar can be a superpower. Largely, this amounts to figuring out how to say “no” respectfully, helpfully, and more often.

Mac, Windows or Linux? Windows.

Kirk, Picard, or Janeway? Picard. But, go Janeway!

Transporter, time machine or cloak of invisibility? Philosopher’s Stone is missing from the list, so I’ll go with time machine. However, I will travel back in time to the moment the cloak of invisibility was discovered and find it myself the day before. Then I would travel forward in time to whenever the Philosophers Stone becomes and option.

If someone gave me $1 million to launch a startup, I would Put the money in the bank and use the interest to fund experiments with the aim of developing a cogent startup thesis that warrants putting $1 million to work at day zero.

I once waited in line for: I waited in line to see Star Wars when it first hit the theaters.

Your role models: I often find myself channeling great entrepreneurs and investors I’ve known. What would Andy do? What would Dan do? What would TA do? What would Chris do? What would Dave do? Without fail, I immediately see the issue/questions/challenge/decision in a new light. It’s palpable. I don’t always take the action I think they would but I’m always informed by what I think their perspective would be. Of course, I could be terribly wrong about what they would actually do if I were to ask them, but the exercise is so effective and immediate that I wouldn’t want to break it by actually asking them. Besides, none of them have time to take speed dial calls from Bob.

Greatest game in history: D&D. Viva la imagination.

Best gadget ever: Staedtler 2.0mm mechanical pencil … and paper.

First computer: I learned to program on VAX-11 in high school, then got excited about computers with my best friend’s TRS-80. I really wanted the Osborne 1 to be my first computer but they were so expensive that I had to eventually settle for building an IBM XT Clone.

Current phone: Samsung S8+. Every time someone switches from an iPhone to an Android, an angel gets its wings.

Favorite app: I love, love, love Audible. Audiobooks are a secret weapon for sure. I even read the Mueller report in less than two weeks while driving to and from meetings.

Favorite cause: My “favorite” is youth entrepreneurship, which I think is an important and valuable cause and it’s something I think I am especially equipped to help with. But I don’t think it’s nearly as important as so much other work that needs to be done in the world.

Most important technology of 2019: Boring old social media has proven its ability to fundamentally subvert democracy. That needs to be fixed. I can’t think of much that’s more important than that.

Most important technology of 2021: AI … for as far out as our headlights go.

Final words of advice for your fellow geeks: My advice is for early entrepreneurs. Having good ideas is easy. The hard part is determining whether and how some good idea or other could also be a successful business — before you sacrifice your savings account, your relationships and your emotional health. Mostly, good ideas turn out not to be good businesses.

And to be clear, I’m not just talking about the ideas that only half the room thinks are good. I’m also talking about the ideas where everyone in the room thinks the idea is good, i.e., that the problem should be solved, that the product should exist and that the world would be a better place with your startup in it. If it were only the marginally good ideas that failed then the startup failure rate would not be in the neighborhood of 95 percent.

Aye, the allure of an idea that everyone tells you is “such a good idea” is irresistible. Coupled with your passion, confidence and ambition, keeping an open mind about whether your good idea can also be a good business is super hard. So hard that you barely paused before jumping off the cliff.

Reid Hoffman famously described entrepreneurship as the act of jumping off that cliff and building a plane on the way down. He is right. But he didn’t say you had to design the plane on the way down. You can do a lot to figure out which planes might possibly be built in the distance from the top of the cliff to the bottom. Of course, certainty is impossible; but there are ways to reduce your chances of disintegrating on impact at the bottom of the cliff.

Passion is helpful, even necessary; but it’s not sufficient. You also need a lot of customer development, some math and a little critical thinking. Constantly be on the lookout for assumptions you are making, i.e., what would have to be true in order for your startup to be a good business? Notice that this is a different question than “what would have to be true in order for your startup to be a good idea.” Ideas don’t come with labels that identify them as a good business or not. You have to figure that out yourself. To do that, talk to lots of customers and then identify and quantify as many of your assumptions as possible and model them in a spreadsheet. If you can’t tell a cogent and quantifiable story about how you could get from here to there (wherever you think “there” should be) then you are operating at a ridiculously high level of uncertainly and risk. Founder, meet cliff.

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