The Advantage #09: Cutting Horse Opens for Business, New Jobs Get Invented, and the Right Partner Changes the Outcome

Welcome Note:

Thanks for tuning into the ninth episode of The Advantage. Back to just plain old Mike writing this one. A short, weekly note where I share what I am working on, something worth watching, a lesson from history, and one practical edge you can try right away.

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What I am Working On: Open For Business!

A little over a year ago, Chris Protaswich and I decided there was a better way to invest in consumer product and service companies. We recruited our Freshly and Petfolk colleague, Henry West, and set out to build it.

A little background.

Chris was on the team at Highland Capital Partners that led Freshly’s Series A in 2015. Which is where we met almost 11 years ago to the day. We were both fortunate to be mentored by the legendary Bob Davis, who was Chris’s boss, a member of my board, and a lifelong friend to both of us.

Chris later went to Wharton for his MBA, and I recruited him out of Wharton to join me at Freshly. At Freshly, Chris, Henry West, who had just come over from Deutsche Bank as a junior financial analyst, and other members of our team ran a three-part process simultaneously. We were raising a Series D and received multiple term sheets, we kicked off an IPO process and selected a bank, but we ultimately sold the business to Nestlé in October 2020.

A few days after we sold, I told Chris he was going to hate working at Nestlé, but not to worry, I had a better option.

A few weeks later, Chris joined Petfolk as employee number one, alongside my sister, Dr. Audrey Wystrach, DVM, to help turn her idea into a real business. I stayed at Nestlé for another year and joined Petfolk in 2022. Henry joined us a few months later. By 2024, Petfolk was well on its way, and Chris and I started talking about building something new, but in many ways something very old.

Venture capital has changed a lot, even since I first raised capital in 2015. Funds have gotten bigger, and the pressure to build unicorns, and now decacorns, has become intense. VCs hand junior, inexperienced founders tens of millions, and sometimes hundreds of millions, of dollars and tell them to shoot for the moon.

That strategy has worked in parts of technology. In consumer, it has often been a disaster for both founders and LPs.

At the same time, venture has lost many investors with real operating experience. Today, you have a lot of professional VCs with little to no operating experience, and very few with real founder experience. I was lucky. I had Bob Davis, founder of Lycos, and Jason Finger, founder of Seamless, which later merged with Grubhub. I spoke with Bob three to four times a week, and I had a standing two-hour call with Jason every other week. The capital mattered, of course, but their advice and mentorship were priceless. Nothing replaces lived founder experience.

So when we set out to build Cutting Horse, we wanted to build an old-school venture firm. We wanted to invest early and make concentrated, high-conviction bets. We wanted to lean in with operational support and mentorship as fellow founders who have been in the ring, and are still in it.

We believed that if we helped founders build sustainable, profitable consumer businesses, and stayed disciplined on both entry valuations and exit opportunities, we could help create a better ecosystem for founders and for LPs.

We chose the name Cutting Horse because a cutting horse is not a racehorse. It is a ranch horse. It is a working horse. It spends all day cutting one cow out of the herd.

We set out to raise a $50 million fund in what may have been one of the toughest venture fundraising environments, especially consumer venture, in nearly 30 years, all the way back to 2008. It started slowly, very slowly. But our thesis and our approach resonated with LPs, especially those who had been in the industry a long time.

To our surprise, and to our gratitude, we were ultimately oversubscribed and closed at the maximum we agreed to take from the start, $75 million.

In a few weeks, it will officially be one year since we started the fund.

It is still early, but we have made four investments in four outstanding businesses, and we have added two team members, Hayden Cheek and Jimmy Shen. We also recently learned that our fund’s 2025 performance puts us in the top 5% of all 2025 funds, according to Cambridge Associates.

Again, it is early, but it does support our core belief. If you invest with focus and discipline, consumer can be an exceptional category for both founders and investors.

If you know a consumer product or services business doing between $1 million and $20 million in revenue, and they are looking for investors who bring more than capital, send them our way.

We are open for business!

Here are a few additional articles if you want to read more about Cutting Horse.

Inc Magazine: They Built a Meal Delivery Unicorn. Now They Have $75 Million to Invest in the Next Big Thing

Yahoo Finance: Cutting Horse Closes Oversubscribed $75 Million Fund I to Partner with Founder-Led Consumer Brands

Axios: Cutting Horse raises $75 million for first fund

Worth Watching

Quick intro:

When people ask me why I am optimistic not only that job growth will continue post AI, but also that humans will keep moving toward better, more fulfilling work, I point to the fact that 200 years ago, 85% of the world’s workforce was focused on food production, 100 years ago it was 75%, and now it is about 25% of the world’s workforce. This shift has been driven by a roughly 10x increase in food production per employee. Or I point them to a 2024 radiology study showing that as radiology adopted more AI, workloads and demand for radiologists increased. But when people ask me for an example of new, more fulfilling jobs that did not exist a few years ago, I point them to one of the most fulfilling YouTube channels I have found: SB Mowing.

Some stats & my point:

SB Mowing has 3.2 million subscribers, has posted 266 videos over the last 6 years, and has received almost 406 million total views. It's number one video, She thought I was CRAZY til she REALIZED there's a SIDEWALK there, which is 53 minutes long, has over 24 million views. Based on different benchmarks, this channel is likely generating $1 million to $1.5 million per year from ads and sponsors, and the catalog is likely worth more than $6 million.

What does SB Mowing do? Landscaping. Literally landscaping. He has averaged about 44 jobs/videos per year, so a little under 1 job a week. I do not know about you, but if you had told me 10 years ago there was a landscaper making $1.5 million a year doing less than 1 job a week, I would have said there is no way. While I do not think millions of people will become millionaires making landscaping videos, I do know that 20 years ago there was no such thing as the creator economy, which Goldman Sachs estimates will reach half a trillion dollars by 2027, with an estimated 50 million global creators. None of these jobs existed 20 years ago. Where will the next 50 million jobs come from? I have no idea, but I am betting my money they will be better and more fulfilling than the ones that get replaced.

Here is my 20-second recap if you do not have the full 53 minutes:

AHHHH WOW!: These videos are surprisingly fulfilling and satisfying. But also a complete waste of time. Worth at least one watch

Lesson From History: Operator Capital Wins When It Concentrates

What Happened:

Sequoia Capital wasn’t founded by a professional investor, or even a previous investor. Don Valentine started it in 1972 after building his career in semiconductor sales and marketing, including as National Semiconductor’s founding VP of Sales and Marketing. Sequoia’s first fund was $3 million, which forced concentration and forced involvement. At Cisco, Sequoia didn’t just provide capital. It pushed to professionalize the company early and helped bring in experienced leadership to scale it. That combination, operator DNA, concentrated capital, and real operational support, produced outcomes that worked for founders and for investors.

Insight behind it:

The best investors don’t just spot momentum. They create it. They know the domain, they pick fewer companies, and they treat ownership like responsibility, not a logo. Big funds can afford to be passive, but often at their LPs’ and founders’ expense. Operator funds cannot.

Modern application:

If you’re a founder, raise from operators first. Not because they will be more “founder-friendly". Because they have better judgment, they got from real experience, and they will stay in the fight with you. Sequoia’s early model is the standard: small enough to care, concentrated enough to commit, and experienced enough to help. If an investor can’t lean in, they’re not worth a meaningful spot on your cap table. Long-term success comes from finding partners who bring more than just capital. It worked for Sequia, their investors, and their early portfolio companies, including Apple, Cisco, and Atari.

Practical Edge: Find A Partern

Why it works:

When you are building anything, my advice is simple, find the right partner.

Building is hard. It can be lonely, messy, and confusing. I have also found that one plus one often equals three or four. That is especially true when your partner balances you with different skills, personality traits, and strengths.

The right partner does not just share the work. They expand what is possible.

The data supports it:

In venture-backed startups, solo founders usually get punished, and teams get rewarded. First Round Capital analyzed a decade of outcomes and found that teams with more than one founder outperformed solo founders by 163% in revenue, and that solo founders had seed valuations that were 25% lower.

Startup Genome found that solo founders take 3.6 times longer to reach the scale stage, and they are 2.3 times less likely to pivot when reality changes.

The same pattern shows up in life. In a meta-analysis of 148 studies covering 308,849 participants, people with stronger social relationships had a 50 percent higher likelihood of survival. In large population research, the relative risk of death for married versus non-married people was 0.88 for men and 0.90 for women, which means married people had a meaningfully lower mortality risk.

This is not about a partnership being romantic or soft. It is functional.

The right partner increases capacity, reduces blind spots, and keeps you steady when the pressure spikes. If you are trying to build something hard, stop treating partnership like a nice-to-have. It is a real performance advantage.

How I use it:

I have been very fortunate to find incredible partners in both work and life.

First, Carter Comstock at Freshly. Then my sister, Aud, also known as Dr. Audrey Wystrach, with Petfolk, and Chris Protaswich with Cutting Horse. And by far the most important, Kerry Wystrach, my wife.

Every one of these people has made the journey sweeter, the hard times easier, and my strengths stronger.

No matter what you are building in life, try to find a partner. It will be a lot more enjoyable, and your odds of success will go up.

Thanks for reading,

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