Why Founders Feel Alone, and What Fixes It | Scott Finkelstein, Yutavis

What we talked about.

Sunny Ray talks with Scott Finkelstein, a founder and coach who has spent a decade advising founders and leaders and is now building Yutavis. Scott describes the dinner two years ago when he realized he was alone, and how reaching out to a mentor and his Austin community helped him feel connected again. He explains how coaching started as a job after the company he ran as CRO was sold in 2019, and why he now treats it as a purpose. He shares a story about a founder who ignored his hiring advice, and explains the idea of the isolation tax, where people think alone because they are embarrassed to share or do not know who can help. Scott also covers what Yutavis, short for path to advanced insights, can do that a human coach cannot, why founders feel lonely even with a team, how to tell when someone needs rest instead of strategy, and his goal of helping 10 million people find a coach. The conversation ends with where to learn more.

Scott Finkelstein explains the isolation tax founders pay by thinking alone, and how a coach, human or AI, can fix it.

The questions, and the answers.

After that dinner two years ago, what did you decide on the drive home?

After everyone left, I realized I was alone, and I decided to reconnect with one of my mentors. From there I reached out to my community in Austin, where there are a lot of founders and startups, to ask whether I was the only one feeling this way. Sharing stories was cathartic and helped me not feel alone.

When did coaching stop being a favor and start looking like a company?

In 2019 the last company I ran as CRO was sold and became private equity owned. I decided to become a coach, but I saw it as my next job, not as entrepreneurship. People I'd worked with always said I was a coach. Someone later told me I had a business, not a job, and I became more successful once I treated it that way.

What is a piece of advice you gave that a founder ignored, and what happened?

A founder wanted to make his first hire, someone who had sold millions and had a network. I said the person wouldn't fit the culture, especially with just him and his co-founder. He hired anyway. Within six months the person was gone, and the issues left to clean up almost put the company out of business.

What can an app do for a founder that a human coach cannot, and the reverse?

An app is there at 2 a.m., on a plane, or in an Uber, instantly. I can't answer a text during a podcast. But people feel more connected to a human. Some clients use Yutavis, then come back to me for an hour to go deeper. I see technology as a bridge for when the human isn't there.

Why do so many founders feel alone, even with a team around them?

It's a lonely journey because most people don't think this way. Most are afraid to put three years of struggle into something, yet accept a comfortable salary for forty years. School and our parents train us to get a good job. Even entrepreneurship classes often teach it as a path to a job rather than what the journey really takes.

How do you know when a founder needs strategy and when they need rest?

When a client keeps coming back to the same thing and can't see the forest for the trees, even as I guide them another direction, it's time for rest. I'll say let's take a break, go for a run, hit golf balls, or take a nap. You have to get to know your clients to recognize that moment.

What did you believe about coaching in 2019 that you no longer believe?

I believed coaching was a business. Now it's a purpose. Back then I walked every session methodically from A to Z with a formula. Now I coach the human, helping them get out of their own way and see what they already know. I'm not a psychologist, to be clear.

You want to reach 10 million lives. What has to be true for that to happen?

I have to create something meaningful that people keep coming back to, and early feedback says Yutavis is that. A lot of people can't afford a high-end coach like me. I built it for people struggling in their lives and careers, not the founder with $20 million in the bank, and I'll keep listening to feedback.