Waseem Daher is co-founder and CEO of Pilot, the largest provider of bookkeeping, tax preparation and CFO services for startups and small businesses. He was once a contestant on Jeopardy!, where he answered 11 questions correctly, won and promptly lost $8,200, and learned that it really is all about the buzzer.
I think it’s important for a founder to be fairly opinionated, especially when you have imperfect information and there’s no way to be sure that you’re making the right call. I’m still learning this; I have a natural tendency to agree with the last person I talked to. But I’ve realized that when I’m more reserved while I mull something over and then make a decision I can really stick to, there’s less thrash for the team. Your team needs you to make decisions, even if you have to make adjustments down the road—and even when they’re not unanimously popular.
This gets harder as a company grows, too. When you’re four people, you can make everyone happy most of the time. At 200, that's just not possible. Right now, for example, we’re thinking about our return-to-office strategy, and of course, some folks are very eager to get back while others would rather stay remote. I think the key is fostering a culture where people understand we will always face those tough choices—and we will always try to do whatever’s in the best interest of the company.
Other founders. That includes my co-founders, Jeff and Jessica. We met as undergrads at MIT and this is our third startup together, so there’s a lot of shared context and trust that’s allowed us to sharpen our decision-making. We also lean on other entrepreneurs as sounding boards—in fact, a couple of months ago, we organized a Slack group called “Founders Helping Founders,” where people can ask for advice on everything from org design to interviewing to tools.
You always have to take other people’s guidance with a grain of salt, because no two companies are alike. The way you go upmarket, or the marketing channel that yields the best results—that’s probably specific to your business. But if you want to get better at something like motivating your team or delegating—which is often hard for founders as a company grows—it’s nice to get a sanity-check from someone who’s seen the movie before.
Targeting a large market. Most first-time founders need to sharpen their intuition on this, because it’s difficult to internalize. You think, “Yeah, a lot of people have this problem, and a lot of money is spent here.” But we aren’t used to thinking about the orders of magnitude involved in building something truly enduring. In our first company, we had cool tech that no one else had, but it was solving a bit of a niche problem compared to what we’re doing with Pilot. If we had kept going, at some point we would have hit a ceiling.
Another important step is to develop a deep, visceral understanding of your customer and what they care about. There are no cheat codes; you just have to spend time with them. Even as the company grows—it can be tempting to let someone else handle it and summarize for you, and you absolutely should eventually hire user researchers and other people who specialize in those conversations. But it’s not a substitute for getting in the weeds and being on the call.
Staying focused on the right things. You can only do so many things really well, and it can be very, very hard to know when to stay the course and when to adapt. If you get new information or a customer asks for a feature, you might want to incorporate it into your plan. But keeping everyone rowing in one direction is how you maintain forward progress.
I think this is a challenge for individual founders as much as for companies, and it’s another thing that shifts over time—in the early days, it’s good to have your hands in lots of things, because it helps you intimately understand the business, which lets you make better decisions. Later on, that same instinct will turn you into a blocker. There’s a lot of stuff I’m still working on letting go of, mostly around how we communicate with our customers. I’m learning not to confuse stylistic preferences with actual results; there’s a big difference between doing something wrong and doing it differently than I would have. If something’s really a problem, I’ll eventually hear about it. Otherwise, it’s about hiring great people that you trust and empowering them to do the work.
Pilot is more process-oriented than most companies—our view is that there are no people problems, only process problems. If we don’t follow up quickly with a prospective customer, for example, then the question is, “Okay, how can we improve the process to fix that?” Our baseline assumption is that everyone on the team is smart and hardworking, so when something goes wrong, the solution has to be something other than “try harder.”
We also watch the metrics more than most startup founders, in part because we bootstrapped our first company and learned to care a lot about cash flow. For example, I don’t think, “Oh, our bank balance is X, so we can spend up to Y.” Instead, we ask: How much have we earned the right to spend based on our current revenue, gross margins, sales and marketing efficiency and NPS? That’s not to say we take a defensive approach—we plan for success and try to make the right investments to that end. But just because we have money doesn’t mean we should spend it. It should be a sober calculus.
Sometimes talking it out with Jeff and Jessica is enough. When the COVID-19 recession hit, for example, most of our peer companies took a “bite the bullet” approach, with one big round of layoffs right away. That was the financially conservative strategy, and we recognized the wisdom of that approach. But we also had very high conviction in this team and believed we had the cash position to weather the storm. So we held on. While there may have been no right answer at the time, we did have a strong feeling about what we should do.
When those conversations aren’t enough, I like to take an empirical approach. Is there some way to test the decision? I don’t think I’m smart enough to read customers’ minds, so whenever possible, I like to have the market tell me the answer. You can have a bunch of drawn-out debates in a conference room—but in the same amount of time, you can probably ship an experiment and actually find out whether people want it or not.
It’s hard to know how the world will react post-pandemic. But one thing we’re seeing concretely, and that I do think will be fairly durable, is a new recognition from both employers and investors that while there are very real benefits to having people together in an office, there are also very real benefits to accessing talent in many different places. Talent is distributed all over the world. It’s a balance—at Pilot, for example, while we’ll likely return to our offices, it won’t be a return to the pre-COVID status quo.
I hope this time will also help all of us remember to prioritize time with family and friends. That’s always been important to me. Admittedly, my wife and I are new parents, so I wasn’t exactly on track to leave the house much over the past year or so anyway! But I do think it’s been a healthy reminder not to take the people we love for granted.
- Be opinionated
- Learn to let go
- Test your decisions