Mindset of a Serial Founder

In my career, I’ve started five companies and a nonprofit. I’m now on the verge of launching my sixth Startup. As my excitement builds leading up to the launch of my new business, it has made me nostalgic as memories resurface from all the past launches I’ve gone through.

There is so much advice on how to launch a business. Evidently, you’re supposed to build a community, grow an email list, create a social media following, use the latest growth hacks, automate with AI, do direct email outreach, and capitalize on your extremely large personal network. Oh yeah! You must build a huge personal network too! Didn’t you know that?

Every time I see a social media influencer posting about being a Startup guru or pushing people toward some growth hack, I either roll my eyes or laugh. I eventually paid for YouTube Premium just to stop seeing the ridiculousness that is pushed toward Founders.

Rather than wasting money, time, and precious energy on these tricks, Founders should simply start.

Sounds Crazy Right?

Experienced Founders learn that all you really must do is launch your product. Put it out into the world and start pushing it toward the potential customers you have the easiest access to. Avoid the big launch parties and growth hacks. Instead, focus on getting customers—even if it’s only a few. Make them extremely happy, and then push out again. This is how you get started.

This is why I love when experienced Founders get involved in a growing Startup community. The practical advice they provide can be extremely valuable to aspiring Founders who are seeking to build their new ventures. This experience can be a game changer in another Startup’s success.

However, the truth is that every Startup is different. Whether you are a first-time Founder or have launched a hundred companies, there is a lot to learn from each other. Too often, early Founders seek out wisdom from experienced Founders, hoping they can guide them to success—and this is a great strategy.

But experienced Founders often forget what it was like when they started their first company from the ground up. Remembering how to be scrappy and do more with less is a foundation that many experienced Founders lose over time.

So here is some advice I have learned first-hand and observed through my own failures and successes:

Experienced founders are not created equal

Some experienced Founders exit with a huge ego, preaching that everyone should follow the exact path they took. They become “startup gurus” who act like they know best. Anybody pushing a “my way or the highway” approach should be avoided.

I observed a Startup who found success when a part of their platform took off. They cut everything else, raised a little money to help them grow and were rapidly growing quickly. Their success came from offering a freemium model that caused users to flock to the service, and while this was good for them, this rarely works for startups.

Their growth was tremendous, but their profitability was low. They were struggling to acquire paying customers and had to continue to raise funding to exist. During this time, the Founder bought a fancy car and would tell everyone that the secret to entrepreneurship is simply to “go free!” Many people followed his advice and none of them exist today.

Experienced Founders can Learn from First- time Founders

I take this advice to heart because I learned it the hard way. After many years of starting companies, my own ego began to inflate. Out of the five companies I started, only one was widely successful. However, three of the five made money. I felt like I knew how to spin up a business and make money, even if it didn’t work out in the end. This was reinforced with my fourth business, which took off to an insane level.

But something critical happened to my mindset as a Founder: I forgot what it was like to build without funding. When we launched my fifth company (while the fourth was still successful), I began solving problems with money. I dropped $20,000 into the company account at formation, and I easily spent another $40,000 on future growth. I focused on buying solutions instead of solving the problems myself.

Now, not all problems need to be solved directly by Founders. We did build all our own code for our platform. But when marketing issues came up, we just ran ads, printed flyers, and hired salespeople to help. This approach slowed us down—until we started to get scrappy again.

Lesson to Be Learned: First-time Founders are scrappy. This scrappiness forces you to work more closely with your customers. We discovered better avenues for funding and new opportunities when we returned to our roots as Founders.

Experience Doesn’t Matter, What You Learn From it Does.

Experience in starting many Startups buys you one piece of knowledge that I wish all Founders learned early on: no Startup is the same. You could start the same company ten times and still find yourself on ten unique Startup journeys.

Founders who understand this often find success across multiple ventures because they approach each one from a humble position of learning. They seek out customer feedback, focus on their financials, and surround themselves with great people to build strong teams. This is the experience you can tap into from seasoned mentors.

But don’t forget—your lack of experience can be your greatest weapon. Without ego, and by staying scrappy for as long as possible, you gain the freedom to experiment and the hunger to keep building. When you focus on creating a product that truly meets your customers’ needs, your inexperience keeps you curious, adaptable, and open to possibilities others might overlook.

However, every new and experienced Founder should seek out a community of other entrepreneurs. You’ll learn from one another, challenge each other, and find support in ways you never expected.

The lesson is simple: Experience will give you tools, but community will sharpen them. Surround yourself with Founders who push you, and you’ll go further than experience alone could ever take you.