#67: 6 Lessons I Learned Working With Over 300 Founding Teams

#67: 6 Lessons I Learned Working With Over 300 Founding Teams

Read Time: 3 min

Today, I’m going to discuss what I learned and have admired working with hundreds of entrepreneurs in my career. Being an entrepreneur is one of the most rewarding and scariest things you can do in life. The highs and lows can literally lead you to insanity.

In my experience, it is imperative to have a balanced life outside of business that addresses the four big things: mental health, physical health, spiritual health, and a strong support system. If you have these things dialed in, you’re good. It’ll still be rough, but you’ll have the cornerstone of what you need to get through.

Friends and family who are not entrepreneurs will never understand. They’ll think you’re crazy, with good reason, because most of us are. It’s a lonely path, and your circle of friends will become tighter and will consist mostly of other entrepreneurs.

In this issue, I’ll share what has inspired me and the consistency that I've seen among the best.

Only in the darkness can you see the stars.

~ Martin Luther King Jr.

Over the last seven years, I’ve worked with over 300 early-stage founding teams, most of which have been funded by the top seed investors and accelerators on the planet.

Here are 6 things that I learned working with the best founders on the planet.

1. Number one is by far the most important. They are coachable. Coachability is trusting the process, and the quicker you come to grips with understanding that you don’t know what you don’t know, the faster you will ramp up and hire people who can help fill in these gaps. The number one trait of successful founders is this. They are intellectually curious, are learning machines, and have very little ego. They learn, apply, and iterate. That feedback loop over time compounds and makes them highly effective operators.

   
   

2. They are all about optimizing to become better and finding a path to profitability as quickly as possible. They go on the offense by going out and learning how to predictably acquire customers through selling rather than hiding behind screen coding to delay the inevitable that you will have to understand in order to see success. They don’t break the rules; they rewrite them. They rarely listen to conventional wisdom.
   
   

3. They’re maniacal about finding the right ICP and positioning the value props in a way that resonates best, constantly iterating based on feedback and data until they achieve a perfect alignment between the product and the market needs. Their relentless focus is driven by a deep understanding that product-market fit is not a one-time achievement but an ongoing process of refinement. They continuously test, tweak messaging, and refine their approach to ensure that every touch point with a prospect or customer—whether it’s a sales call, a marketing campaign, or even a customer support touchpoint—is aligned with the needs of their target audience.
   
   

4. They don’t try to solve every use case; they only focus on those that will have a real residual effect, zeroing in on the specific use cases that matter most to their ideal customers. By doing so, they maximize impact and drive meaningful results without diluting their efforts. Focusing on the big needle movers allows them to develop deep expertise in solving high-value use cases, leading to a more defensible market position. Rather than trying to solve every pain point a customer has, they channel their focus into perfecting solutions that generate long-term value.
   
   For ex: If you want to feel better, start by committing to the gym. And eventually, you’ll eat better, sleep better, go to bed earlier, and feel better. The one main use case you solved for will unlock the rest.
   
   

5. They actively look for people with broken legs and eliminate the ones with bum knees. If I have a bum knee, it‘s uncomfortable, but I can get around. If I have a broken leg, I’m incapacitated; I need help immediately. When you build out your MVP and go to market, you have a hypothesis of what your MVP can solve. You validate that hypothesis by going out and asking people to buy it. You have to find the people who have broken legs to get insights into whether or not you’ve built something the market wants; if so, great deals will come. If not, you will aggregate data through the qualification process that’ll help you iterate the product and pivot in the direction the market directs you to. Either way, it’s a win-win.
   
   

6. They sell as they build, ship fast, and use base hits to help fund iterations while keeping burn at bay—moving them closer to profitability. The idea is to go out and find buyers and deliver a product that fulfills that need. This approach not only provides base hits (cash flow) but also creates a feedback loop that allows you to pivot and improve the product. Your goal early on is to stay alive and to stay lean to keep the burn rate low, to keep the runway long, and to reduce the pressure of securing additional rounds of funding. You want to stay nimble and pivot quickly to market shifts while building toward product market fit.
   

That’s it for today!

See you all next week.



Darren

P.S. If finding PMF and scaling to $1M in ARR through founder-led sales is on your radar, book a call with me here

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