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Freedom & Family

October 2026 • 46:25

Build a Business That Gives You Your Life Back with Kenneth Kollasch

What happens when the business you built for freedom starts taking all of it? Kenneth Kollasch joins Ben Davis to talk about the someday fallacy, protecting family time, stabilizing after growth, and testing an idea before building it.

FeaturingKenneth KollaschBusiness coach, Kenneth Coaches

Key Lessons from This Episode

Three ideas worth taking from the conversation

Kenneth Kollasch on the milestones that keep moving, the value of stabilizing after growth, and the people we keep promising to make time for.

01

Someday is not a day on the calendar

Kenneth calls it the someday fallacy. Once the business hits a number, once the next hire works out, once the current rush is over, we will have time for the rest of our lives.

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02

Make room for the business to stabilize

Kenneth describes three stages: start, scale, and stabilize. Entrepreneurs tend to enjoy the first two. The third can feel less exciting, even when it is the part the business needs most.

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03

An idea people like still needs customers

Kenneth also shared a mistake he made himself. After writing his book Beating Average, he built a life-skills platform around part of the material. He believed it could help people. He did not do enough research to establish the market for it.

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I asked Kenneth Kollasch about building a business that gives you your life back. We ended up talking about the calendar.

That makes sense when you think about it. A calendar is where our priorities become real, or where we find out that they are still just things we say matter.

Someday is not a day on the calendar

Kenneth calls it the someday fallacy. Once the business hits a number, once the next hire works out, once the current rush is over, we will have time for the rest of our lives.

He sometimes asks clients to open their calendars and read the days aloud. Monday. Tuesday. Wednesday. There is no someday. It is a simple exercise, but it gets at a difficult question: have we actually made room for the people we say we are doing this for?

Kenneth grew up around entrepreneurs. His parents ran a ballroom dance business, and business was a regular conversation at the dinner table. He saw opportunity in that world. He also saw what it could cost when family members worked opposite schedules.

Today, he protects mornings with his wife and a day each week for their relationship. Those are his choices, built around his life. The useful part is making an actual choice instead of waiting for a milestone to make it for you.

Make room for the business to stabilize

Kenneth describes three stages: start, scale, and stabilize. Entrepreneurs tend to enjoy the first two. The third can feel less exciting, even when it is the part the business needs most.

Growth changes the demands on a team. New people, processes, and responsibilities need time to settle. If we keep pushing without checking whether the business can hold what we have already built, more growth can bring more pressure.

Stabilizing gives you room to see what works without your constant intervention. It also gives you a chance to notice whether the way you are running the business matches the life you wanted it to support.

Before the next push, ask what still depends entirely on you. Which decisions keep coming back? Which routine problems keep interrupting the day? Those questions can point toward the systems that need attention.

An idea people like still needs customers

Kenneth also shared a mistake he made himself. After writing his book Beating Average, he built a life-skills platform around part of the material. He believed it could help people. He did not do enough research to establish the market for it.

He spent about two years on the venture while other businesses competed for his time. The return did not justify what he was putting into it. This was advice he gave clients, and he admitted he had not followed it himself.

There is a difference between someone saying an idea sounds good and someone choosing to pay for it. Before building every part of a new business, Kenneth recommends taking inventory of your time, energy, resources, and network, then testing demand.

Talk to the people you hope to serve. Learn what they are trying to solve. Give yourself a chance to hear something inconvenient while changing course is still relatively simple.

Ask what you actually want

One story stayed with me. Kenneth was considering an opportunity to play professional soccer. After a match, he sat down with his grandfather expecting a conversation about the achievement. Instead, his grandfather asked whether it was what he really wanted.

That question made room for more than a career decision. Kenneth thought about marriage, family, and the kind of life he wanted to build. An exciting opportunity still needed to fit those things.

We talked about the people who help us ask better questions: spouses, coaches, mentors, pastors, and family. People who know us well enough to challenge an idea before we spend years chasing it.

You do not have to copy Kenneth’s calendar. Start by looking at your own. What keeps getting postponed? What could you protect this week? What needs to stabilize before you add something else?

Those are useful business questions. They are also useful life questions.

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Meet the Guest

Kenneth Kollasch

Kenneth Kollasch is a third-generation entrepreneur, pastor, and business coach behind Kenneth Coaches. He works with small service businesses and franchise owners on the systems, leadership, and boundaries that help a business support the life its owner wants to live. In this conversation, he shares lessons from his own ventures, including a life-skills platform that failed to find a market.