Blog Startup Journey

What 9 Successful Entrepreneurs Wish They Had Done Differently

wrote this on

We all have our own, but sometimes it’s better to learn from the regrets of others.

In 2004, many of us had the opportunity to become shareholders in Google for the very first time. Most of us passed on that offer. Had we decided to invest, by cashing out today, we would make more than $5 for every dollar we put in.

To me, that’s a regret.

And it's not my only one: We’ve all made decisions (or failed to make decisions) we wish we could take back. I shared many of mine last year.

Even the most successful entrepreneurs are no different. I asked nine founders about their biggest regrets in business.

And I learned a lot from what they shared. I hope you do, too:

1. Hiten Shah, KISSmetrics and Crazy Egg

Regret: Not looking for problems.

Most of my early failures were a result of building things people didn't want. What I would have done differently is to find the right problem to solve for customers before writing a single line of code. It would have saved me a countless amount of time and resources. ⁠—Hiten Shah

2. David Hauser, Grasshopper

Regret: Not investing in culture.

I wish I had focused more time, thought and money into the company culture from day one. I have since discovered this to be the most important factor in the success of scaling any business. Core values, core purpose and integrating these into everything will give the largest returns you will ever see as a founder. ⁠—David Hauser

3. Noah Kagan, Sumo

Regret: Not connecting with a mentor.

I would have gotten a mentor who's done the things I wanted to accomplish in the future. Why not learn from someone who's already done the things you want to do? People will read this and still not do anything. Instead, send one email to the person you respect in business the most, asking for a chat. You'll be surprised how much it energizes you and helps you succeed. ⁠—Noah Kagan

4. Dharmesh Shah, HubSpot

Regret: Not selling sooner.

One of my bigger regrets in my first startup is hanging on to it too long. I ran that company for about 10 years. I had acquisition offers along the way, but the valuations never matched my growth projections. I probably held off on selling that company for three to four more years than I should have. I knew that I was no longer excited about the industry, and had aspirations to do something different⁠—and hopefully bigger. Eventually, I did sell the company, which freed me up to go back to MIT for graduate school⁠—and ultimately start HubSpot. If you're heart's not in it, be willing to make the sacrifice to let something go so you can free yourself up for whatever new things are ahead. ⁠—Dharmesh Shah

5. Andrew Warner, Mixergy

Regret: Not asking for feedback.

When I got my first customers at Mixergy, I was embarrassed to ask them why they bought and what I could do to improve Mixergy for them. I thought they were going to tell me that there were too many things to improve because my site sucked. When I finally started calling them, I heard about a lot of things that needed improving, but my customers really liked me and my work, and many of them offered to help improve what wasn't working the way they wanted. ⁠—Andrew Warner

6. Wade Foster, Zapier

Regret: Not trying new things in school.

I would have definitely experimented with more stuff in high school and college. Programming, science, selling: I was a bit too shy and nervous about my social image to try different things, and I ended up having some catching up to do. ⁠—Wade Foster

7. Adii Pienaar, WooThemes and Receiptful

Regret: Not living in the moment.

I was obsessed about always moving from point A to B to C, which meant I was never really present in any given moment. This also meant that the highs on the rollercoaster ride were fleeting, and the lows, always brutally around-the-corner. I've since learned to enjoy the journey itself (more than the destination) and appreciate small victories and special moments much more. ⁠—Adii Pienaar

8. Mike McDerment, FreshBooks

Regret: Not being focused.

In the early days of building FreshBooks, I struggled to find focus. As an entrepreneur, you see opportunity everywhere. It’s in your DNA⁠—your business becomes a hammer, and everything looks like a nail. I could see an infinite number of paths that the company could take. I was fortunate enough to have a good advisor who taught me an invaluable lesson before I managed to killed the company. He said, “Mike, there’s a four-letter word in business: FOCUS. If you don’t focus, you’ll be drowning.” He encouraged me to pick one thing and go as deep as possible… and [to do that] just when I thought it was deep enough, to push harder, because you can always go a hell of a lot further than you initially think. ⁠—Mike McDerment

9. Jason Lemkin, SaaStr

Regret: Not picking a committed co-founder.

Never co-found a company with anyone, no matter how talented, that isn't committed for at least seven-to-ten years. It takes that long to build anything that really matters. ⁠—Jason Lemkin

How To Apply This To Your Business

These are the things that successful people would’ve done differently, but that doesn’t mean that they’re the things that are right for your business.

However, I hope that by sharing these with you, I’ve given you some ideas for mistakes to look out for that you might be making, or strategies to be thinking about as you grow.

It’s impossible to do everything right, always.

But by examining our decisions after the fact—even if we don’t dwell on them—we can learn a lot about how to make better decisions in the future.

(An earlier version of this post first appeared on Entrepreneur)

1,143 Shares
← Older Post Newer Post →

From “aha” to “oh shit”, we’re sharing everything on our journey to $10M in annual revenue. We’re learning a lot and so will you.

2016 Annual Revenue
  • $0
  • $2.5M
  • $5M
  • $7.5M
  • $10M

About the Author

Alex Turnbull is the CEO & Founder of Groove (simple helpdesk software for small businesses) who loves to build startups and surf.

You might also like: