0016 - Why Bigger Deals Are Safer: Tim Kolb on Scaling Wealth Through Business Acquisition

Business Buying for Financial Independence

In this episode, Tim talks with Tim Kolb, an entrepreneur who knows what it’s like to build a business from the ground up—only to realize the cost of chasing growth without balance. Tim Kolb shares the unfiltered story of how he and his wife grew their first business with no formal training, the emotional toll of burnout, and the decision to sell when life demanded a new chapter. He also dives into how that experience reshaped his approach to entrepreneurship and what he’s doing differently in his next ventures.

Tim is an entrepreneur who believes everyone should explore the opportunities that business and real estate can provide on the path to financial freedom. He owns and operates a wine & liquor store, a software startup, a consulting company, and a growing portfolio of commercial and residential real estate.

Tim’s passion for independent business has led him to support dozens of other business owners. For over a decade, he has worked with businesses on strategy, processes, finances, and marketing. These experiences, along with analyzing dozens of other businesses for potential acquisition, have provided Tim with an immense knowledge base to pull from.

Tim has appeared on multiple top‑tier podcasts in the financial space, such as Bigger Pockets Money and The Freedom Chasers Podcast.

[00:00 – 14:32] Starting from Scratch

How Tim and his wife dove into business ownership with no formal training. The steep learning curve of building a business from the ground up. Early challenges that shaped their entrepreneurial mindset.

[14:33 – 34:58] The Cost of Chasing Growth

Why burnout became inevitable in their first venture. Recognizing when the business was no longer sustainable. How personal life (COVID, new parenthood) accelerated the decision to sell.

[34:59 – 57:16] Selling and Starting Over

Lessons from the sale of their first business. How selling became the catalyst for the next phase of life. The emotional and practical realities of walking away.

[57:17 – End] Rethinking Entrepreneurship

How the experience reshaped Tim’s approach to business ownership. Creating ventures with sustainability and balance in mind. Tim’s advice for entrepreneurs feeling stuck or burned out.

Guest Bio Tim Kolb is an entrepreneur who built his first business from scratch alongside his wife, navigating the highs of growth and the lows of burnout. After selling that business, Tim has refocused his entrepreneurial journey on sustainable ventures and meaningful work.

If you found value in today’s show, make sure to subscribe so you never miss an episode packed with insights to help you buy and grow a business that creates real financial freedom.

Connect with Tim Kolb: Instagram: tim.kolb.09LinkedIn: linkedin.com/in/timothy-kolb/

Connect with Tim and the community on social media for more tips and updates:

Website: https://www.powerofbiz.com

YouTube: https://www.youtube.com/@powerofbiz

Instagram: https://www.instagram.com/timtdelaney/

Threads: https://www.threads.com/@timtdelaney

LinkedIn: https://www.linkedin.com/in/timothytdelaney/

Facebook: https://www.facebook.com/timtdelaney

Tweetable Quotes:

"Sometimes quitting isn’t failure — it’s making space for what’s next." – Tim Kolb "Building a business from scratch taught me more than any classroom ever could." – Tim Kolb "If growth costs you everything else, it’s time to rethink the plan." – Tim Kolb "Selling our business wasn’t the end — it was the beginning of a new chapter." – Tim Kolb