Ep 257 The Most Important Numbers and Drivers with Lee Benson

02/25/25 • 52 min

Profit Answer Man: Scaling with Profit First & Beyond

The Most Important Numbers and Drivers with Lee Benson

Welcome to another episode of The Profit Answer Man, where we dive deep into the strategies and mindsets that drive business profitability and sustainable growth. Today, we’re joined by Lee Benson, a serial entrepreneur who has successfully built and sold multiple businesses, including a nine-figure exit to Textron.

Lee brings decades of experience in business strategy, leadership, and value creation. His passion for helping organizations increase their impact and profitability is evident in his work as the CEO of Execute to Win, a firm dedicated to enhancing organizational effectiveness.

If you’re a business owner looking to scale profitably while navigating growth challenges, you won’t want to miss this episode!

In this episode, you will learn:

How Lee took a failing company, assumed its debt, and turned it into a highly profitable venture.
The key lessons from scaling a business from $0 to a nine-figure exit.
Why hitting plateaus in business growth is normal and how to break through them.
The importance of aligning leadership with the needs of the company at different stages.
How to develop a sustainable growth strategy that maintains profitability.
The biggest mistakes entrepreneurs make when scaling and how to avoid them.

Key Takeaways:

Take Smart Risks and Own the Outcome – Lee turned a struggling company around by assuming its debt, securing customers, and focusing on value creation. Many entrepreneurs hesitate at the idea of taking on debt, but when done strategically, it can be a powerful tool for business growth.
Growth is Not Linear – Scaling a business involves hitting revenue plateaus before making the next big leap. Lee experienced these plateaus, such as being stuck at $8 million for a few years before unlocking the next growth phase.
Be the CEO Your Company Needs – One of the biggest lessons Lee shared is that business owners must evolve as leaders. Each stage of business growth requires different skills, mindsets, and strategies.
Focus on Profitability Over Revenue – A mistake many business owners make is chasing top-line revenue without ensuring profitability. Lee emphasized the importance of maintaining strong profit margins while scaling.
Execution is Everything – Scaling isn’t just about strategy; it’s about execution. Lee’s company maintained a 20%+ annual growth rate by continuously refining operations and executing with discipline.

Guest Bio:

Lee Benson is the founder and CEO of Execute to Win, a company dedicated to helping organizations maximize their value. He is a serial entrepreneur who has started and grown multiple businesses, including Able Aerospace, which he successfully sold to Textron in a nine-figure deal.

Lee is also a sought-after speaker, author, and podcast host of Show Your Value. His expertise lies in value creation, leadership, and execution, and he has been featured in major publications like The Wall Street Journal, Forbes, and Inc.

Conclusion:

Scaling a business isn’t just about growth—it’s about profitable growth. Lee Benson’s journey demonstrates the importance of strategic risk-taking, leadership evolution, and disciplined execution.

If you’re an entrepreneur looking to break through revenue plateaus and build a high-value business, start by implementing the key lessons from this episode.

Links:

https://www.linkedin.com/in/lee-j-benson/

https://www.etw.com/

https://www.facebook.com/ETW.executetowin

https://www.instagram.com/executetowin/

https://www.youtube.com/@execute-to-win

Watch the full episode on YouTube: https://www.youtube.com/@profitanswerman

Profit First Toolkit: https://lp.profitcomesfirst.com/landing-page-page

Relay Bank (affiliate link): https://relayfi.com/?referralcode=profitcomesfirst

Profit Answer Man Facebook group: https://www.facebook.com/groups/profitanswerman/

My podcast about living a richer more meaningful life: http://richersoul.com/

Music provided by Junan from Junan Podcast

Any...

The Most Important Numbers and Drivers with Lee Benson

If you’re a business owner looking to scale profitably while navigating growth challenges, you won’t want to miss this episode!

In this episode, you will learn:

How Lee took a failing company, assumed its debt, and turned it into a highly profitable venture.
The key lessons from scaling a business from $0 to a nine-figure exit.
Why hitting plateaus in business growth is normal and how to break through them.
The importance of aligning leadership with the needs of the company at different stages.
How to develop a sustainable growth strategy that maintains profitability.
The biggest mistakes entrepreneurs make when scaling and how to avoid them.

Key Takeaways:

Take Smart Risks and Own the Outcome – Lee turned a struggling company around by assuming its debt, securing customers, and focusing on value creation. Many entrepreneurs hesitate at the idea of taking on debt, but when done strategically, it can be a powerful tool for business growth.
Growth is Not Linear – Scaling a business involves hitting revenue plateaus before making the next big leap. Lee experienced these plateaus, such as being stuck at $8 million for a few years before unlocking the next growth phase.
Be the CEO Your Company Needs – One of the biggest lessons Lee shared is that business owners must evolve as leaders. Each stage of business growth requires different skills, mindsets, and strategies.
Focus on Profitability Over Revenue – A mistake many business owners make is chasing top-line revenue without ensuring profitability. Lee emphasized the importance of maintaining strong profit margins while scaling.
Execution is Everything – Scaling isn’t just about strategy; it’s about execution. Lee’s company maintained a 20%+ annual growth rate by continuously refining operations and executing with discipline.

Guest Bio:

Conclusion:

If you’re an entrepreneur looking to break through revenue plateaus and build a high-value business, start by implementing the key lessons from this episode.

Links:

https://www.linkedin.com/in/lee-j-benson/

https://www.etw.com/

https://www.facebook.com/ETW.executetowin

https://www.instagram.com/executetowin/

https://www.youtube.com/@execute-to-win

Watch the full episode on YouTube: https://www.youtube.com/@profitanswerman

Profit First Toolkit: https://lp.profitcomesfirst.com/landing-page-page

Relay Bank (affiliate link): https://relayfi.com/?referralcode=profitcomesfirst

Profit Answer Man Facebook group: https://www.facebook.com/groups/profitanswerman/

My podcast about living a richer more meaningful life: http://richersoul.com/

Music provided by Junan from Junan Podcast

Any...

Previous Episode

Ep 256 Scaling Businesses Across Industries: Lessons from a Serial Entrepreneur with Philip Taylor

Scaling Businesses Across Industries: Lessons from a Serial Entrepreneur

In this episode of The Profit Answer Man, we sit down with Philip Taylor (PT), a CPA turned entrepreneur, to discuss his journey in building multiple successful businesses. From launching a finance blog in 2007 to creating major conferences like FinCon and TravelCon, and now running a CPA firm for content creators, PT shares his insights on diversification, adapting to industry changes, and maintaining profitability.

If you're an entrepreneur looking to build multiple income streams, navigate the shifting digital landscape, and optimize your financial strategies, this episode is packed with actionable insights!

In this episode, you will learn:

How Philip built and scaled multiple businesses in blogging, events, and accounting.
The major shifts in blogging and digital content creation over the years.
How AI and search engines have disrupted traditional content models.
Strategies for running a profitable conference and event business.
Key financial mistakes content creators make—and how to avoid them.
The importance of tax planning, retirement strategies, and financial systems for entrepreneurs.
Why building a financial war chest is crucial for long-term success.

Key Takeaways:

1. Diversification is Key to Long-Term Success. Philip didn’t rely on just one business—he built multiple streams of income:

PTMoney.com – A personal finance blog that started in 2007.
FinCon – A major annual conference for personal finance content creators.
TravelCon – A travel content creator event.
The Creator CPA – A tax and accounting firm focused on digital entrepreneurs.

Each of these businesses operates differently, but Philip has found ways to integrate them so they support each other.

2. The Changing Landscape of Blogging and AI's Impact. Blogging used to be a hub for conversations, but social media took that engagement away. AI-powered search engines now provide direct answers, reducing website traffic for independent bloggers. Google prioritizes big media brands over independent creators, making it harder for small content sites to rank. Many creators are shifting to email newsletters, YouTube, and social media platforms where they can directly engage audiences.

3. Running a Profitable Conference Business. Philip runs two major creator-focused events, but COVID and rising travel costs disrupted the event industry. His advice: Build financial reserves so you can weather downturns. Continuously evolve your model—smaller events, hybrid events, or alternative pricing strategies may be needed. Understand the true cost for attendees—it’s not just the ticket price; flights, hotels, and food add up significantly.

4. Financial Mistakes Entrepreneurs Make. Philip sees common financial pitfalls among entrepreneurs, especially content creators:

Not setting aside 20% of income for taxes.
Ignoring retirement planning (e.g., Solo 401(k)s, SEP IRAs).
Mixing personal and business expenses.
Failing to build a financial war chest to handle downturns.

Solution: Work with a CPA, separate personal and business finances, and prioritize long-term financial stability over short-term spending.

5. Tax Planning vs. Tax Preparation. Most CPAs focus on tax prep (reactive) instead of tax planning (proactive). Strategic tax planning can help business owners reduce taxable income, plan for retirement, and optimize deductions. Meet with your CPA in September/October to plan before year-end.

Tip: If your business revenue fluctuates, consider using Roth conversion strategies during low-income years to maximize tax advantages.

About Philip Taylor:

Philip Taylor (PT) is a CPA, entrepreneur, and founder of FinCon. He also runs The Creator CPA, a tax firm specializing in financial services for content creators. His insights have been featured in The New York Times, Forbes, The Washington Post, and other major media outlets.

Conclusion:

Philip Taylor’s journey proves that multiple revenue streams, financial planning, and adaptability are key to long-term entrepreneurial success. Whether you’re a content creator, business owner, or service provider, his advice on tax planning, cash flow management, and business diversification can help you increase profitability and protect against economic downturns.

Links:

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

Twitter: https://x.com/ptmoney

https://taylorassociatescpa.com/cpa-for-content-creators/

Watch the full episode on YouTube:

Next Episode

Ep 258 Scaling Success: Transforming Your Business into a Powerhouse with Courtney De Ronde

Scaling Success: Transforming Your Business into a Powerhouse with Courtney De Ronde

Welcome to another insightful episode of The Profit Answer Man! In this episode, we sit down with Courtney De Ronde, CEO of Forge Financial and Management Consulting, to discuss the crucial intersection of financial management and business growth. Many businesses struggle not with generating revenue but with understanding what their numbers mean and how to take action on them. That’s where Courtney and her Simple ScaleUp SystemTM come in, helping business owners move from financial confusion to confident decision-making.

If you’re looking to scale your business while keeping financial clarity, this episode is a must-listen.

In This Episode, You Will Learn:

How your financials tell the story of your business and why most accountants stop short of helping you act on them.
Why management consulting and financial expertise should go hand in hand for business success.
The Simple ScaleUp SystemTM and how it helps entrepreneurs translate financial insights into action.
How small businesses can bridge the gap between financial data and strategic decisions.
The key factors that separate thriving companies from those that struggle financially.

Key Takeaways:

Financial Reports Are Just the Beginning. Most business owners get financial reports but struggle to act on them. Courtney highlights how her firm goes beyond the numbers, ensuring business owners understand the "why" behind their profit margins.
The Missing Piece in Accounting – Business Strategy. Many accountants provide historical financial data but don’t connect the dots to operational decisions. Courtney’s firm helps entrepreneurs answer the big question: "Now that I know my financials, what should I do next?" This bridges the gap between data and strategy.
Scaling Requires Systems, Not Just Growth. Scaling a business isn’t just about increasing revenue—it’s about ensuring your systems, leadership, and financial clarity grow alongside it. The Simple ScaleUp SystemTM provides a structured framework for making scaling intentional and profitable.
Profitability Isn’t Just a Math Problem – It’s a Leadership Issue. Your profit and loss statement won’t explicitly tell you if you have poor leadership, a toxic culture, or inefficient systems—but it will show up in your bottom line. Courtney shares how business leaders can spot these inefficiencies early and take action before they eat away at profits.
CFO Services Aren’t Just for Big Companies. Many small businesses think they can’t afford financial leadership, but outsourced CFO services provide big-business financial strategy on a small-business budget. Whether through bookkeeping, tax strategy, or high-level consulting, having a financial expert on your team is a game-changer.

About Courtney De Ronde:

Courtney De Ronde is the CEO of Forge Financial and Management Consulting and the creator of the Simple ScaleUp SystemTM. With 20+ years as a CPA and 15 years in leadership, she helps business owners understand their numbers and take action toward growth. Her firm provides a mix of financial expertise and management consulting to help businesses and nonprofits scale successfully without financial blind spots.

When she’s not helping businesses thrive, Courtney enjoys road-tripping with her husband and three kids from their home base in Des Moines, Iowa.

Conclusion:

Scaling a business isn’t just about making more money—it’s about making smart, sustainable financial decisions. Courtney De Ronde delivers a refreshing perspective on the power of financial clarity, showing how combining numbers with strategy is the ultimate formula for success.

If you’ve ever felt like you’re drowning in financial reports but don’t know what to do next, this episode is for you.

Links:

Website: ForgeAhead.com

LinkedIn: in/CourtneyDeRonde

Facebook: /ForgeFMC

https://www.forgeahead.com/resources/simple-scaleup-system-e-book/

Watch the full episode on YouTube: https://www.youtube.com/@profitanswerman

Profit First Toolkit: https://lp.profitcomesfirst.com/landing-page-page

Relay Bank (affiliate link): https://relayfi.com/?referralcode=profitcomesfirst

Profit Answer Man Facebook group: https://www.facebook.com/groups/prof...