Who is your hero?
I really look up to entrepreneurs who are able to create a professional and personal life on their own terms. So often I feel like the media only covers one kind of company: venture-backed tech startups, usually out of a major incubator. There’s absolutely nothing wrong with that, but there are so many ways to start and own a business. I love reading stories about entrepreneurs who leveraged their business success to take time working in the community, to travel, or who just have a strong sense of pride in having created a great place to work.
What’s the single best piece of business advice that helped shape who you are as an entrepreneur today, and why?
It’s a cliché, but you really have to get used to failing all the time in ways big and small. But this isn’t just about personal resiliency — failing quickly helps you understand what works. As we built our marketing program, nearly everything that I thought would be effective turned out to be either mediocre or an outright failure. And many channels that weren’t in my original business plan turned into huge successes. You have to plan to try a lot of different things, gather data, and make hard decisions about what to continue.
What’s the biggest mistake you ever made in your business, and what did you learn from it that others can learn from too?
I moved too slowly bringing on full-time help for sales, marketing, and administration. I thought that I had special insight into our customers and a special affinity for selling our product. That wasn’t the case at all. In fact, we now have salespeople who routinely outperform my old records. Put another way, I wish I would have known how smart and capable a team I could have put together earlier. I would definitely have done so, even if it meant going back to Ramen noodles for a few months.
What do you do during the first hour of your business day and why?
I know it’s not the recommended approach, but the first thing I do is check my email and deal with any critical issues from the night before. I hate to have issues hanging over my head when I’m trying to get to my “real work” — building my company. I turbo through important communication that I can deal with right away, then set aside time to deal with larger issues if necessary. I can then turn off my email for several hours in the morning and get through my daily priorities.
What’s your best financial/cash-flow related tip for entrepreneurs just getting started?
For the vast majority of bootstrapped companies, it’s incredibly important to start generating paying customers, even if the terms aren’t ideal for your business model. For example, I started by doing some tutoring myself as I launched our tutoring company. I then slowly added more instructors. Many tech entrepreneurs do some consulting as they work on scalable products. This also gets you immediately engaged with your target customer so you can iterate a better product plan.
Quick: What’s ONE thing you recommend ALL aspiring or current entrepreneurs do right now to take their biz to the next level?
GET HELP! There’s no way you can do everything on your own. There are dozens of little tasks that distract you from the core task of building a product and taking it to your customers. Cash flow is usually tight, especially at first. But you’ll be surprised how inexpensive a team of great contractors and freelancers to help you with your website, graphic design, social media, bookkeeping, and administration can be. I definitely went into it thinking I had to take on all those responsibilities rather than hiring a freelancer for $20/hour to do it faster and better than I could.
Companies grow when the founders spend time on their most important goals. They get stuck in the mud when you spend a day fiddling with your business cards.
What’s your definition of success? How will you know when you’ve finally “succeeded” in your business?
In terms of our business, I’ll feel like we’ve succeeded when nearly every potential customer who would be a good fit for our program knows about us and considers us as an option. We’re in an industry where brand recognition and word-of-mouth referrals are paramount, and we’re working hard to build that.
Personally, success for me is being able to build great products and services because I want to, not because I have to. The flexibility to work how and when I want is incredibly valuable to me.