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.

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.

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.

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.09
LinkedIn: 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

"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

In this solo episode, Tim Delaney breaks down the five red flags you need to watch for when evaluating small businesses for sale. From mysterious add-backs to shaky contractor structures, Tim explains how to separate real opportunity from risky deals—and how to spot warning signs before you’re locked in.

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.

Tim sets the stage and explains why spotting red flags early is critical when buying a business.

Why seller add-backs can sometimes be justified—but often hide inflated earnings.

How unclear or unstable leases can sink a location-dependent business.

The danger when a seller can’t clearly explain their financials.

Why the promise of “potential” should make you stop and think twice.

The risks of a workforce made entirely of 1099 contractors.

Tim’s closing advice on focusing on real cash flow, not empty promises when buying a business.

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 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

“Mysterious add-backs are one of the biggest warning signs in a business listing.” – Tim Delaney
“If the seller can’t explain their own numbers, that’s your red flag right there.” – Tim Delaney
“There’s no such thing as ‘potential’ you don’t have to work for.” – Tim Delaney
“Cash flow clarity beats growth promises every single time.” – Tim Delaney

In this episode, Tim talks with Brad Cornell, a seasoned entrepreneur and business buyer who brings a no‑nonsense perspective to acquiring and running small businesses. Brad doesn’t sugarcoat the challenges of business ownership—he dives into what it really takes to go from dreaming about buying a business to successfully running one. He shares how his journey reshaped his understanding of financial freedom, why courage and resilience are non‑negotiable, and the mindset shifts that separate successful buyers from those who burn out.

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.

Why buying a business takes “balls of steel.”
Debunking the myth of the “easy buy.”
The emotional and mental prep needed before an acquisition.

What financial freedom really costs (and why it’s worth it).
Brad’s personal stories of sacrifice and course‑correction.
Setting realistic expectations for your first acquisition.

The difference between running a job and running a business.
Why hands‑off ownership in year one is a dangerous myth.
Lessons from Brad’s biggest pivots as an owner.

How to develop a sustainable, growth‑oriented mindset.
Staying engaged without burning out.
Redefining what success looks like beyond revenue.

Brad’s no‑filter advice for anyone considering a buy.
Building resilience when the unexpected happens.
The key relationships that make acquisitions succeed.

Guest Bio
Brad Cornell is an entrepreneur and small business owner who has bought and operated multiple companies. With an unfiltered approach to entrepreneurship, Brad shares hard‑earned insights on courage, resilience, and the true cost of financial freedom.

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 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

"Financial freedom doesn’t come without a cost." – Brad Cornell
"If anybody tells you buying a business is hands‑off, question them heavily." – Tim Delaney
"Business ownership isn’t autopilot; it’s engagement, every single day." – Brad Cornell

How do you go from relying on a “safe” corporate job to building a business of your own? In this episode, Tim talks with Dennis Geelen about his life-changing journey from being laid off at 43 to becoming a consultant, author, and entrepreneur. Dennis shares the wake-up call that pushed him to bet on himself, the lessons he learned from building a solopreneur practice, and why business acquisition can be a smarter and faster path to financial independence. Whether you’re stuck in a comfort zone or looking for your next chapter, this episode delivers practical advice on risk, resilience, and building a life on your own terms.

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 – 07:45] The Wake-Up Call: Laid Off at 43

Dennis shares his journey from corporate leadership to being laid off.
Reflects on the risks of relying solely on a “safe” paycheck.
Discusses the emotional and financial challenges of starting over.

[07:46 – 16:15] Building a Solopreneur Business

How Dennis transitioned into consulting and writing.
Lessons learned from building a personal brand and business from scratch.
Why leaning into your passions can create new career opportunities.

[16:16 – 25:00] Business Acquisition vs. Building From Scratch

Why buying a business can shortcut the path to financial independence.
Insights on what to look for in a business acquisition.
How to evaluate opportunities that align with your skills and goals.

[25:01 – End] Rethinking Risk and Building for the Future

The mindset shift needed to take control of your career and finances.
Encouragement for starting side projects as a safety net.
How to use setbacks as fuel for long-term growth.

Guest Bio
Dennis Geelen is a consultant, author, and TEDx speaker who helps businesses become more customer-centric and innovative. He is the founder of Zero In Consulting and the author of four business books, including The Zero In Formula. Dennis is passionate about helping professionals embrace entrepreneurship as a pathway to freedom and fulfillment.

Connect with Dennis:
Website: zero-inconsulting.com
Personal Site: dennisgeelen.me
LinkedIn: Dennis Geelen

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 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:
“Doing nothing can be riskier than taking the leap.” – Dennis Geelen
“Don’t wait for a layoff to start building your future.” – Dennis Geelen
“Side hustles aren’t just hobbies—they’re safety nets.” – Dennis Geelen
“The real risk is putting your financial future in someone else’s hands.” – Dennis Geelen

In this solo episode of Business Buying for Financial Independence, host Tim Delaney steps away from guest interviews to share an honest look at the downsides of business ownership. While Tim is a strong advocate for buying small businesses, he makes it clear: it’s not for everyone.

From stress and uncertainty to the myth of passive income, Tim breaks down the realities you’ll face if you’re considering business acquisition. This episode will help you decide if you’re truly ready to take on the challenge.

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.

The hidden weight of being the “last line of defense.”
Payroll, inventory, and team conflicts → it all lands on you.

Lessons from Jocko Willink’s Extreme Ownership.
Why taking responsibility (even for others’ mistakes) is key.

Why business ownership is never truly “hands off.”
The “planting a tree” analogy → hard work before fruit.

Tariffs, demand shifts, and supplier risks.
Why entrepreneurs must act without full information.

Stress from employees, customers, banks, and even family.
How stress tolerance determines success.

The importance of mentors, advisors, and delegation.
Why refusing help will cap your business’s growth.

Resilience under pressure.
Comfort with uncertainty.
Willingness to rely on and empower others.

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 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:

“Owning a business is not truly passive income.” – Tim Delaney

“You are the last line of defense for everything.” – Tim Delaney

“If you want to do everything by yourself, your business will never grow beyond what you can do.” – Tim Delaney