Reflecting On Our First 5 Years: 5 Things I Wish I Knew At The Beginning

It doesn’t feel like five years. In fact it feels like just yesterday I was sitting down at my  kitchen table to figure out how to start a company. So much has happened since then, and without the support of my now-wife-then-girlfriend who apparently missed the memo that being an entrepreneur basically means you’re unemployed, none of this would be possible. I’ve watched in amazement as we’ve grown – bigger offices, new website iterations, the launch of this newsletter, new clients, new investments, and most importantly – more team members. The impact of adding each and every one of the people on our team has reverberated through the entire business, taking it somewhere I never could have even flirted with on my own. Through all of that, I’ve learned countless lessons – many the hard way – but on the whole have found these challenges far more rewarding to power through than those that came before. In honor of our 5th Birthday, here’s five things I’ve learned that I wish I knew at the beginning.

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Always Be Selling Like You’re Going Out of Business

This sounds obvious enough, but things are tricky in a services business when you’re an army of one. We don’t sell widgets, and we didn’t invent a better mousetrap. We don’t cold-call CEOs, suggest it’s time that they replace their CFO and offer to help them with that. Sales cycles are all over the place. The shortest has been 1 week, the longest – well I’ll know the answer when we start doing work for companies we started building relationships with the year I founded the firm. In the beginning, I was worried that I’d sell too much and not be able to deliver on the work without having a team to support me. In hindsight, this was bananas. This would have been a wonderful problem to have. Alas, it was not the problem I had. After some reps, I quickly learned that I always needed to have the same urgency around our business development efforts as I did around our delivery. This got easier once our team grew and I could split my focus more evenly, but the reality is, no revenue, no business. Even when things are going well, get your ass out there and sell more.

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Hiring The Right People is Transformational‍

Duh, right? Shameless plug for a search firm? Maybe. But if you want to trace the first inflection point in our business, there’s an exact date that just happens to match up with our first hire. You have to white-knuckle your way through the productivity dip that follows, but when you come out the other side of it, the return on investment is huge. When you get it right, you see the early formation of your company’s culture, you get freed up to focus on other things (see Lesson #1), the next hire gets incrementally easier to on-board via shared institutional knowledge, and, it gets a little less lonely. Just a little. There’s a chicken and egg element to this when you’re bootstrapping the business and haven’t raised capital, but there hasn’t
been a single thing that we’ve spent money on that has a better return on investment than our people.

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Understand Why People Say No To You, But Even More Importantly, Why They Say Yes.

In the beginning, I heard “No” a lot. A lot. Turns out, starting a company is an exercise in getting your teeth kicked in every day, and coming back for more. Good thing my dad’s a dentist. When we wouldn’t win an engagement, I very infrequently knew why. I could take a good educated guess, but rarely would a prospective client tell me straight up. One-man shop, track record, etc. Over the last year, a number of our clients have told me why they said “yes” to us, and it was a strangely profound realization that that was probably more important for me to understand. I should have asked every damn client we had why they picked us, because some of the unsolicited feedback surprised me. It highlighted that they cared a lot about the things about us that I thought they should care about, but feared they didn’t. They chose us because of our size not in spite of it, our clear focus, and the belief that we would do anything to deliver for them. It showed me that the story about us that I wanted to tell, was in fact the one that people wanted to hear. Who would have thought? Which leads me to my next lesson…

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Trust Your Gut

You know. You know you know. But you zig when you knew to zag. At what point do you start to listen to that feeling that clearly knows better than you? I should have listened more often. I’m happy I listened when I did. Instinct led me to make some bold (for me) calls over the last few years at times when all the evidence said not to. A number of those moments represent huge inflection points in our business, and frankly are why we’re still here. Other times I didn’t trust my gut, and I really should have. This one requires constant awareness on my part, because I still miss it sometimes, but I’m getting a lot better at paying attention. I think the brain subconsciously does a phenomenal job of cataloguing experiences in the form of data, and when it’s trying to tell you something based on all of that computing power, you should listen.

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Balance is A Key To Longevity

I say “A” and not “The” because there are others, but this one has been hugely important for me. In the beginning, at that lonely table in my one bedroom apartment, 10 feet from my bed, it was hard to figure out when the work-day started and ended. Even sitting on the couch in the evening, being able to see my “office” led to pangs of guilt. I’m starting a company, shouldn’t I still be working? I think the answer was no. This is a marathon, not a sprint. Finding time to get above it, rest, reset and come back ready to go made a big difference. Taking the occasional vacation to realize that I could and the world wouldn’t come to an end was really important. We just aren’t meant to keep going without taking a break, and I’ve got to set a good example. Happy employees make for a happy company and happy clients, and they need to know that it’s not only OK to rest and reboot, but that it’s an expectation. As a founder, I had to be deliberate about placing boundaries (with some flexibility) for the benefit of everyone, not just me.

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What I’m Working On

I, like our company, am a work in progress. I find that when I share what I’m working on out loud and with others, it helps keep me accountable to it. There are two things that I’m trying to improve on daily. The first is patience. And not the “I’m an impatient person and that’s a weakness masquerading as a strength” type of a BS answer to an interview question. I mean impatience in a form that I’m not proud of. It’s something that I’ve been working on for a long time, and probably always will be, but it’s important to me, my team, and my family that they get the best, most patient version of me so that we can continue to do amazing things.

The second thing, is stopping to celebrate the wins. I think we’re like most growing companies, in that we spend a lot of time unpacking the things that we mess up, or fail at, and very little time patting ourselves on the back for a job well done. I’ve been guilty of this my whole life, but I’m making a concerted effort to focus on our wins – big and small – because we should and it’s important. I worry that if we don’t we may forget how to have fun doing this, and if we’re not having fun, what’s the point?