This is Andrew Gunderman’s weekly newsletter, a place to find his upcoming events, news, and to read about technology, business / startups, economics, and investing.

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👀 Who is Andrew Gunderman?

I am a young entrepreneur who raised venture capital for the first time at 21 and dropped out of college that same year. I sold my first company at 23.

I also host both private and public events for celebrities, professional athletes, influencers, elected government officials, business magnates, and more. Many thousands of people have attended my events all over the country, and I've raised hundreds of thousands of dollars in sponsorship.

I was named on the Inno 25 Under 25 list for 2023. You can find me in Entrepreneur, Forbes, Inno Magazine, and more.

🎉 My Upcoming Events

• The Quarterly Penthouse Series is the premier private event in Chicago aiming to be THE event for the most accomplished people in the city. Featuring professional athletes, celebrities, influencers, business magnates, high ranking and elected government officials, and more. These events feature guests worth billions of dollars and who have millions of social media followers.

  • Early March - For extremely accomplished individuals in any field

• Renowned Chicago is the premier private community for established influencers & content creators in Chicago. Our community represents a membership with a cumulative 80 million followers on socials.

  • Mid April - For established influencers or content creators making any type of content (30k minimum followers or some major accomplishments)

That’s it for now! If you’re interested in attending an event just respond to this email and let me know. However, all of my events are curated for specific groups of people, so if you’re not in an event’s target group don’t expect an invite.

😀 Nobody Buys Companies. They Buy Systems of Running Companies.

When someone buys your company they don’t buy it just so they can say that they bought it. They buy a system, an engine, that already works in generating revenue at a certain rate. Often, your business will be valued and acquired at a certain multiple of revenue or EBITDA.

EBITDA

EBITDA stands for Earnings Before Interest, Taxes, Depreciation, and Amortization. It’s a fancy metric that measures what some call a more “accurate” measurement of business health. An interesting note about these measures of business health is that when you sell your company people will look beyond what your recent revenues are. They will expect to see evidence of a system of business that works, and has been working for a while. This is exactly what I’m referencing when I say that “no one buys companies. They buy systems of running companies.” If you build a company that achieves $100 million in revenue in one month, but then never achieves that again - you will not sell that for such a large number because it clearly isn’t a system of revenue generation. It is a one time success.

In fact, any potential buyer will generally expect to see consistent, repeatable processes across all critical areas of your business—marketing, sales, operations, and finance. They don’t want to step in and have to reinvent the wheel. Instead, they’re paying for a proven system that consistently churns out results. This means having documented processes, reliable data on conversion rates, predictable operating costs, and strong relationships with suppliers and customers. All these moving pieces function together to keep that revenue engine humming.

It’s also worth noting that while growth metrics and profitability ratios are certainly important, they’re only part of the story. Serious buyers are looking for evidence that your business can weather market fluctuations and adapt over time. A system that demonstrates resilience—meaning it can handle a pivot in product offerings, a shift in customer preferences, or even a slight slowdown in the economy—goes a long way in making your company an attractive acquisition target.

Keyman Risk

This is why “one-man shows” with no documented procedures or delegated responsibilities can struggle when it comes time to sell. If everything in the company relies solely on the founder’s personal Rolodex or day-to-day hustle, there’s no transferable system. The moment the founder is out of the picture, the entire operation stalls or collapses. This is called keyman risk. It’s a risk that buyers typically don’t want to pay a premium for.

So, as you scale your business, focus on developing and refining the repeatable processes behind your success. Track your performance, standardize your workflows, and build an organization that can function—even thrive—without you being at the center of everything. By doing this, you’re not only boosting your daily operations; you’re also creating a valuable asset that someone else would be willing to pay a healthy multiple to acquire. And that, ultimately, is what it means to build a company that someone truly wants to buy.

🫠 What I Need Right Now

• Nothing!

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