28 things I’d do differently next time around

Here are the lessons I learned building a company to 500 people and $7B in transactions while raising $125M along the way.


I love reading blogs by founders who try to give back and share what they’ve learned building their companies, so today I’ll try and do the same.

When I look back over the last 15 years building 4 different companies (most recently Bigcommerce), here are some things I’d do different if I was to start another company, as well as a few things I wouldn’t change.

If you’re just getting started, keep in mind that it’s at least a 7–10 year journey, so when the going gets tough I found it can be useful to get some perspective from other founders who have gone down the same path.

Stay focused, be positive and know that even when you “get big” it’s still a roller coaster of ups, downs, highs, lows, fun and fu*ks. That’s why having a big, compelling vision and building a great team around you is so important.

Here’s my list. I hope you find it useful.

Things I’d do differently

  • Hire top down after the first 10 people
  • Invest in design (team or agency) from day one
  • Be tied to your vision and problem statement but not your approach
  • Define customer personas up front and segment by pain/needs
  • Focus on a single pain point and a single persona first
  • Do less, but do it better, especially in product and marketing
  • Start competing in a red ocean but try to redefine the market so it becomes a blue ocean
  • Don’t rely on a single lead source driven by high demand and limited supply
  • See your platform as multiple products not multiple features
  • Hire product managers with strong domain experience
  • Run a 6 month (minimum) closed beta and nail your USP (Unique Selling Point) before going live
  • Go for fewer customers at a much higher ACV
  • Tie a good amount of everyone’s bonus to a customer success metric
  • Build an open platform from day one (RESTful API, also consumed internally)
  • Be patient and work on a 5/7/10 year timeline — ignore competitors and focus on the market opportunity not feature wars
  • Listen to your gut more, especially when it comes to people — assume all resumes are B.S. and back channel at least 5 people who worked with, for and above each candidate
  • Listen to the entire organization (especially those in daily contact with clients) in a way that scales as you grow
  • Build a customer advisory board who are incentivized to provide valuable feedback often
  • Amplify the brand by building and remunerating a team of influencers
  • Understand the 4 styles of leadership and use each effectively depending on the person you’re leading
  • Know which stage your company is in (product market fit, getting ready to scale or scaling) and only read books/blogs related to that stage
  • Make sure all senior leaders have their own executive coaches
  • Listen to and respect opinions, but realize they’re just opinions
  • Don’t be emotional about the business — balance an intense focus on work with family, friends and fitness
  • Realize no one cares as much as you do, and that’s OK
  • Fire fast and be less forgiving of mistakes, especially in departments that are measured with raw numbers, like sales and marketing
  • Don’t speak at conferences — they’re a massive waste of time
  • Don’t assume everyone has honest intentions just because you do
  • Don’t beat yourself up because you make mistakes

Things I’d do again

  • Bootstrap to a MSP then raise a round as soon as you achieve product market fit
  • Recognize people for their achievements in front of the whole company on a regular basis
  • Solve a problem you’ve personally experienced and that you could work on for the next 7–10 years
  • Create a culture that’s different, unique and feels like the founder(s) of the company
  • Constantly ask yourself “who is the BEST person in the world to help me solve X?” and reach out to ask for help — know you can’t fix everything on your own
  • Negotiate hard on valuation to keep as much equity as possible, all the time — give way on terms before equity
  • Early on, raise money from investors who have “been there, done that” — don’t take money from “spreadsheet VCs” because they only understand numbers
  • Hire the best people, regardless of where they are and incentivize them heavily with equity
  • Personally answer as many support inquiries as you can for the first year
  • Own the product for the first year or two to make sure your vision is in the team’s DNA
  • Know who your real competitors are and pay attention but don’t let them distract you from your original vision
  • Be the face of your company and learn how to speak in front of large crowds
  • Be confident hiring people who are twice your age and realize the only place age is a barrier is in your head
  • Celebrate the good times but be brutally honest with everyone when things aren’t going well — and share your plan to get things back on track fast
  • Communicate your vision until you’re blue in the face, then keep talking about it
  • Do what you’re good at and delegate everything else to people who are much, much, much smarter and more experienced than you are
  • Know when it’s time to hire someone to replace you — get a deep understanding of your skills and passions and hire that person before you top out
  • Own the culture and continually shape what it means, reinforce why it’s important and fire anyone who breaches your core values
  • Have zero optionality — no “side project”, no job to fall back on, no plan B. Put your entire life into the company for 2 years then put your head up to assess where you are, how you’re going and decide if it’s time to crank it up or call it a day
  • Get good at pitching your vision and answering tough questions when you’re on the spot
  • Be a genuinely caring person and try to change the world from a place of humility, humbleness and honesty

Get my new book “SANE: How To Build Your Business Rapidly Without Going Insane” at http://www.dontgoinsane.com 📚