Eight Lessons Learned as Entrepreneurs (Original Post: January 2021)

This is not a traditional post, but we wanted to take some time to share some of our learnings. A lot of our customers are small business owners, so maybe this brief change-up will be useful. We’ve been working on this project for a few years and have grown quite a bit in that time. We’re sprinting in our execution and still finding time to balance our hard work with a lot of time for reflection. While these thoughts are written in the context of a software startup, they’re lessons that can be applied to any type of business, even Club Lacrosse and AAU Basketball. Here are a few things that we’re attributing to our success:

1. Be obsessed with product design.

Iterate constantly. Be agile. All those buzzwords, seriously. Nothing that we’ve built is off-limits for a revamp; it can all be improved. We circle back to things that we built 3 years ago at least every couple of months to make sure they still align with the vision or our next round of enhancements. Also, make it pretty. Beautiful products aren’t everything, but they sure help build credibility.
I almost didn’t include this one, because it seemed so basic. But if you’re not delivering an excellent product, go home.

2. Be wary of the Minimum Viable Product (MVP).

I’m all for being agile and testing ideas, but you should always be focused on ideas that scale. MVPs tend to be half-baked and don’t work super well without a lot of manual intervention. Use an MVP to validate that you can solve a problem, then go DEEP, not wide. Building an MVP on top of an MVP is going to bog you down in manual processes and prevent you from innovating further. Try to automate as much as you can, early. It will let you go wide faster, later.

3. Time is your most precious resource, so make it count.

I got caught up early on trying to build a social media following because it was ‘free advertising.’ It cost a lot of my time, and I sucked at it. I passed by opportunities to make our product better by identifying our product-market fit. I am most skilled as a product developer and add the most value in that role. I need to avoid getting caught up in the weeds on things I’m not good at, even if it ‘saves’ money.

4. Pay for help, but only if you’re ready for the help.

You can accomplish a lot, even scale, for either free or extremely low cost. Don’t get sucked into high-cost products that are going to help you ‘scale to 7-figures’ simply because they have some fancy bells-and-whistles. Hubspot is one of the greatest resources and tools that we’ve come across and we hardly paid a dime. Their CRM tool is fantastic, even the free tier. I check their blog and certification courses regularly, for free. Also, buy some books (they’re cheap): The Lean Start-Up will teach how to build a product that solves problems, Building a StoryBrand will teach you how to talk about your product that solves problems.

5. Write effectively.

I’ve always thought I was a bad writer, but I think school is teaching us to be bad writers. Minimum-page requirements are the devil. Make your point in as few words as possible. People will actually read it.

6. Find people that make you better.

My business partner, Ryan, is the ideal business partner for me. We share the same values and bring completely different skillsets to our business. We also have enough general knowledge of the other’s responsibilities to collaborate effectively. We spend about 4 hours together every week with conversations ranging from bugs/product ideation/prioritization to philosophy/religion. I always leave our conversations rejuvenated and motivated to keep going.

Also, my wife, Casey. I’ve spent a lot of time coaching over the last few years. Coaching is my primary source of inspiration to find problems that needed solving. We have two young kids under 3 and the time she’s allowed me to spend away from home doing something I love has been invaluable.

7. Know the difference between feedback and an opinion.

One person giving you ‘feedback’ is generally an opinion. Don’t sweat it until you hear it twice.

8. Don’t waste time on people that say, “maybe.” 

We had a vision that we believed in. We’ve been served much better by finding people that shared our vision and helped us perfect it. People that say “maybe” are usually just too kind to tell you “no” and aren’t ready to understand the vision; we’ll circle back to them later.


A few P.S.’s

1. I originally started writing this as an opportunity to capture some self-reflection. That in itself was useful, but I thought some folks might be interested. Don’t be too harsh on changing tenses and constantly changing pronouns.

2. Point #4 has all kinds of links to free Hubspot resources and Amazon product pages for two books. We’re not affiliated with any of them. They have been tremendously helpful resources in our development and I strongly encourage you to check them out.

This post was originally published on January 23, 2021.

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