What I Learned in My First 365 Days as an Entrepreneur

What I Learned in My First 365 Days as an Entrepreneur
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Founder of Praytell Strategy
5 min read
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Even with a cool 18 months on the books the designation as business owner, much less founder, still feels as ill fitting as a speedo. Just as ill fitting? The idea that insights I’ve gleaned so far might help someone else who has just made the same lonely leap feels a little strange. And yet, the road from an office in my kitchen to a "real" office with a team of 20 has taught me so much, I can’t help but hope my lessons learned will assist someone else pursuing a similar path. With that in mind, here are six of the six thousand things I wish I knew back when I was sitting in my kitchen wondering how it would all shake out.

You’ve got this. Early on, I visited bookstore after bookstore, buying a dozen business books (and skimming a hundred more in-store) in hopes of addressing the knowledge gap I was certain I was lugging around. That was an incredible waste of time and energy. Those insights, though well crafted and well intentioned, almost never related back to my situation in a meaningful way. That’s why it was so important to stop trying to find a silver bullet and instead focus on the task at hand, embracing the temerity that comes with it. Turns out that building an airplane and flying it at the same time isn’t that bad of a business plan. 

And when you do have questions, it may be better to turn to people, not books, for insights. Look for other founders that have gone down the same path as you have or mentors that have years under their belts.

Related: To Make It, You Have to Be Willing to Fall Flat on Your Face

Always bet on talent. If I could take back any investment of emotional energy over the past year, it would be the investment in wondering whether to pull the trigger on talent during times when cash flow was tight (which I later found out was always).

In the end, I’ve ended up making the gamble, and each time I’ve been rewarded in ways I’d never have thought possible. It’s hard finding the people whom you know can step in and make a difference, which means that it’s imperative that you grab them up when given the chance

Addition by subtraction. To that end, I'll never again let someone who isn't a good cultural fit drag down our team. I waited too long in one instance, only to see an immediate benefit after making a cut. It wasn’t just a cultural lift that we experienced, our actual work got better once the pallor was lifted -- with measurable results the very first day after the change. It was a hard lesson but one I’m grateful to have gotten early on.

Thanks (for nothing). I went to 10 banks in the first month, looking for a line of credit and a bit of financial air cover. Turns out that banks don't quite like the service industry, much less a youngster with little other than seven figures of purchase orders to show. I can still feel the doors slamming in my face. While the money it didn't come to me, I later realized it was a blessing in disguise. Not having that security blanket made me think scrappy from day one -- and to adopt financially conservative habits that I’d never ever had before. Sure, it would have been great to get a check on day one, but it turns out we never really needed it anyway.

Related: 3 Unconventional Tips on Building a Startup

The best new-business strategy? The business. It might sound like a cliché, but it has emerged as a core truth to the business: Doing great work is the best new-business strategy there is and investing in the work vs. fancy marketing or a biz-dev staff has been central to our success. I always thought the hard part would be getting new customers, but I was wrong. The hardest part is keeping the level of excellence up -- every single day -- in a way that inherently drives new business, keeps clients happy and the team engaged and energized to do great work.

Ask for feedback. And then ask again. There is an HR saying about how having an open-door policy doesn't mean that people automatically walk into your office to talk -- an insight that has been spot on. It has taken much more proactivity than I thought it would to get people to share their views, especially given our transparent culture. That said, giving team members every avenue I can to share their feedback with me has been an incredibly worthy endeavor, as I’m always pleasantly surprised by how actionable their insights are. 

I’m looking at an editing room floor with another couple dozen tidbits, from the value of supporting greater good, the importance of getting everything -- and I mean everything -- in writing up front, when to forgive debt and when not to, and on and on and on. But perhaps it’s best to end with the most important thing I’ve learned. It’s ok to stop, slow the spinning wheels of future casting, and go get a nice cold beer. In fact, it’s advice I think I’ll take myself this very moment.

Related: Bravely Facing the Epic Decision of a Career Pivot

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