Kyle Mack is co-founder and CEO of Middesk, a company that provides business verification and identity infrastructure to help companies build trusted relationships. He and his teammates—many of whom joined the company post-COVID-19—are getting to know each other via virtual DJ sessions and weekly cooking contests.
Our team talks a lot about the idea of building an adaptive, rather than tactical, environment. Tactical performance is about executing against a plan; adaptive performance is about executing when there is no plan. But even when you don't have a plan, you always have your people. I think back to when I left Vermont, where I’m from, and moved to San Francisco. My parents told me that if it didn’t work out, I could always come home and join the family business; that was part of what allowed me to go out on a limb and see if things would work out. To navigate uncertainty, I think it’s important to stay optimistic and embrace a spirit of adventure.
I think another key in moments of uncertainty is making quick, thoughtful decisions, which requires really understanding where you’re ultimately trying to go—even if you don’t yet know how you’ll get there. A recent example for us came out of the PPP loan program. We suddenly had customers asking for new types of data, to help them decide which businesses to lend to. It was a time-sensitive opportunity, but we still had to step back and consider it, because it wasn’t immediately obvious how those adjustments might fit into our longer-term product road map. By taking time to be thoughtful, we realized one week of work on an existing API would be enough to give our customers a big win.
For almost two years before my co-founder and I started Middesk, I kept an Evernote document called “Notes to Myself,” with all the things I wanted to remember when I eventually started a company—and I do review it regularly. Sometimes I’ll just go back through and see if it sparks any ideas, but most often, I use it as a reference when I’m kicking off a new project. Nothing in there is rocket science, but it helps even to see those small reminders, like, “Communicate a clear vision for the next one, three and five years, even if you don’t have perfect information.”
Another resource I use a lot is the content from Sequoia’s Company Design Program, AMP, which is a 10-week intensive for founders. It’s been really helpful for thinking about how to build a company, not just a product—everything from what leadership means to how we should track performance. I actually include things from AMP all the time in the weekly emails I send to our team.
I think the biggest thing is having an extreme appreciation for the problem you’re trying to solve. When we first started Middesk, we talked to a lot of potential users, and we learned a lot from that, no question. But we learned far more once we were actually verifying businesses and manually poring over tens of thousands of reports. That experience showed us every edge case and exception we needed to address, all the nuances that vary from state to state. It’s what allowed us to make our product better.
And while we’re a bigger team now, we do still try to reinforce those lessons when we bring on someone new. As part of their onboarding process, every employee spends a day doing manual business verification using Middesk. We want everyone to always have our customers’ problems top of mind, because we know building that empathy is what will help us be successful in the long run.
Being deliberate about what you want to accomplish—and then putting your resources behind it. There’s a quote from a book called The Supreme Philosophy of Man that I’ve been repeating to myself lately: “Don’t mistake motion for progress.” It feels reassuring to have a long list of to-dos and keep checking things off, but what really matters is whether those things are having an impact.
We went through this recently when we first started ramping up our Sales team. We spent some time generating pipeline for deals that would have been lucrative, and where the prospective customers were big organizations—but the use cases weren’t actually a good fit for the product we have today. Rather than get distracted by flashy names, we had to remind ourselves of the longer-term vision and focus on things that would get us closer to our North Star.
There are lots of opportunities in our space to do things differently, especially on the product side. We onboard customers instantly; we collect as little information from them as possible; we have an in-house team of quality assurance analysts. Even the delivery model is different. But I do think it’s important to know where you want to innovate and where it makes sense to adopt an existing playbook. Painting a picture of a business from a few simple inputs—there’s no model for that. We are doing something entirely new. But maybe there’s already a good model for how we should build our Sales team. It’s always worth asking ourselves whether we’re reinventing the wheel on something where we could just go ask our board member, Alfred, “What’s the best way to solve this?”
This relates to another theme we took away from the AMP program, actually: be different, not just better. We try to reserve most of our energy for the problems where we have a unique solution, not just an improvement on someone else’s idea.
I think you have to start by understanding what kind of decision you’re making. Is it reversible or not? Is it high-impact or low-impact? If it’s low-impact or reversible, I always try to let the team drive. We expect people to be thoughtful, of course, but if they make the wrong call, it’s okay. As long as we have a framework to quickly determine whether we were successful, we can just adjust where we miss the mark.
The difficult-to-reverse, high-impact decisions are harder, but I think the first step is giving them the space they deserve. My co-founder, Kurt, and I spend a lot of time talking things through, both with each other and with our network—our board, our peers. Then you have to take all of that advice and synthesize it, which is a muscle every founder has to build. It’s easy to fall into the trap of just doing exactly what someone tells you. But it’s much better to take those perspectives into consideration and use them to inform your own decision.
If I get advice and I’m still struggling, another trick I’ve used is boiling down the decision to something binary. With a complex product decision, for example, I might ask, “Will this path help customers trust our product more, or less?” Sometimes that simplification can be clarifying.
I’d like to see spending more time with family and friends become the norm. I got to go back to Vermont for a couple of months this summer, and I saw some people more than I thought I ever would before we all retired.
More broadly, I think going through this period of time has made people understand the value of expertise—we’re all constantly looking for guidance, knowledge, best practices. When offices first started shutting down, for example, everyone wanted to know how Google and Square were approaching that. It seems like there’s a pretty big opportunity for people to position themselves as industry experts and solve problems more holistically, and that expands to the macro level. If we come out of this with more transparency of thought and more shared understanding of potential solutions, that’s a pretty interesting future.
- Make tough decisions binary
- Know when to innovate—and when not to
- Embrace adventure