You already know that after several years, I stepped off the startup hamster wheel. While I’m sure that separation will give me more and much better perspective, I’ve been itching to get some of my experiences down on paper. I’ve been given a wealth of opportunity in this community and am thankful for all it has done for me and my career. But I’m also not so starry-eyed to not see its flaws.
After a startup boot camp program (both as a student and as a teacher), one failed adtech company, one fintech company and one short tour of duty at one of Chicago’s hottest new companies, here’s a non-exhaustive list of things I learned along the way:
Money doesn’t solve all problems.
When I was at my first startup, I daydreamed about what it would be like to have even a $1000 a month to spend on lead generation. At Startup Institute, we used to joke about the low budget the staff had to host events or pay instructors (which was near zero). At the fintech company, I had a bit more cash to spend, but never what I felt was adequate to acquire the kind of clients we were seeking. And then I finally landed somewhere that had seemingly endless amounts of capital to spend.. and found myself wishing we had less.
There was something about having less than we needed (at previous companies) that made us more creative. We were scrappier, and problems got solved faster. Sure, we argued more; but, we also knew exactly what we were spending, what it was delivering and where to make cuts if and when we needed to.
When you have more than what you need, you get comfortable. Maybe too comfortable. Problems get swept under the rug, because you have the luxury of figuring them out later. People get added at a faster pace, and makes team decision making and communication slower and more murky. Software gets purchased (and never used), but no one notices. The environment is just..different. There’s pressure, but it’s not the same kind you feel when there’s not extra millions in the bank.
I spent years thinking the grass would be greener, but I think I’d choose the simplicity of a lean cash-strapped business any day over one that doesn’t recognize its own privilege.
If you’re at an early-stage company, no matter what your job title is, your real job is finding product-market fit.
I can’t shout this one loud enough. Every single startup I worked at was pre-PMF, even if the founders claimed it wasn’t. Each time, I came on board to prepare for a public launch, build a lead gen funnel or scale a growth team. And every single time, I spent the vast majority of my days trying to understand whether the world actually needed what we had built, who the end customers really were and where it best fit. That meant endless hours of calls and meetings with potential users, economic buyers and analysts. Piles of market research from news outlets, trade pubs and associations. Conferences where I would just sit and listen to the intricacies of customer problems, trying to envision how we could twist what had been made into something that would actually work for them.
The hardest part of building a company isn’t building a product – it’s building the right one. It’s acknowledging that the thing in your head that you think is so great, probably isn’t. Then it’s having the humility to go to the market, learn how people work and figure out how to build a solution that actually makes sense.
And since we’re here.. the reason my marketing at the fintech company was so successful? It’s because of all the work I did above. The best way I knew to help get to PMF was to immerse myself in the industry and its problems. The best way I knew to get to the level of expertise that we needed, was to get to a point where I could teach it to someone else. So I challenged myself to write every single week about what was going on in payments fraud. The rest is history.
You can never spend enough time thinking about how your product impacts people.
At the first two companies, it barely crossed my mind. At the last one, where we had the clear and obvious potential to eliminate jobs and people’s livelihoods, I couldn’t stop thinking about it. Every time I thought about framing the product or its capabilities, I struggled with the fact that someone reading my copy was probably seeing “job killer,” no matter what words were on the page.
Empathy is the current buzzword of choice in the product and design communities, but it deserves the attention it’s getting. We don’t spend anywhere near enough time thinking about the larger impact of our products. It’s easy to push the “productivity and cost savings” argument with economical buyers – until you’re sitting face to face with an emotional employee whose entire job is being changed or replaced by the thing you built.
Thankfully, this lesson punched me in the gut very early on in my career, but there are a ton more entrepreneurs who could stand to learn it too.
Tech news stories and startup awards are mostly b/s.
During my tenure at one startup, I helped them win just about every award and recognition out there. And nearly every story we pitched to local tech publications got printed without push back. We said we were successful, so they wrote that we were – no questions asked.
At another startup, we won an award for best new company and got a major nomination for a separate award on our progress before the product had even launched or we had any revenue. People didn’t know what we did, but they knew the names behind it, so the accolades poured in.
I’ll be the first to admit that when you’re grinding through the issues of formulating a company, these are welcome wins. But they also artificially inflate your sense of achievement and make you think you’re doing better than you actually are.
It’s not to say that every company that wins awards doesn’t deserve them (there are plenty that do), but once you see under the hood of this machine, you realize it’s not necessarily about success or impact – it’s about who can spin the best story, who has the most well-known players on their team and who makes the most sense for the city to put on a pedestal as its best and brightest.
There are plenty of businesses out there with sound products, tons of happy customers and no write-ups in ChicagoInno or Pletz’s column in Crain’s. I often wonder if that’s the better path.
Staring financial realities in the face (even if they’re ugly) is better than not knowing at all.
The very first startup I worked at laid me off seemingly out of nowhere, less than a year into my tenure. I was shell-shocked, because I was never told that we had anything to worry about. Turns out the business wasn’t making enough money. They didn’t have enough in the bank to make payroll, and they had to let people go.
After the shock wore off, I chalked it up as the cost of doing business in a startup. And I believed that to be true, until I went somewhere that actually valued transparency.
At another startup, we reviewed how much cash we had in the bank every single week during our team meeting. We knew exactly what our monthly burn was, what revenue was projected, and thus, how many months of runway we had as a business. It was never meant as a fear-mongering technique to get us to work harder, but rather, an honest assessment of where we were as a company so we could feel empowered to make the right decisions for our functional areas. I’d never go back to a business that doesn’t value this kind of visibility and access.
Your team will make or break you.
Starting a business from scratch is hard, but it’s world’s easier when you have a smart, humble and supportive team that can work well together. Luckily, two out of my three experiences landed me on the positive side of that coin. We disagreed, but it was never personal. We screwed up, but we rallied together and moved on. We called each other out on poor behavior, apologized and meant it. And it made the tough moments surmountable.
But when that foundation of trust and camaraderie isn’t there, the climb feels impossible. At this organization, I was fortunate enough to be on a team with some of the most talented people I’ve ever met – but it felt like we were trying to run through a pit of mud. We had some of the brightest minds in Chicago tech in the room, but somehow, every single step was arduous and painful. We could never get ahead. And many of us ultimately ended up leaving.
That said, as a whole, this ride has been fun, challenging, frustrating and has taught me a lot in a very short period of time. It’s brought me some of my closest friends, given me a platform to teach and give back, and helped me clarify what sort of impact I want the rest of my career to have. If you’re wondering what that is exactly, I talk about it in a bit more depth in this post from a few months ago.