Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
Are you trying to grow your business by 10% year over year? You might be leaving massive wealth on the table. In this episode, we sit down with Tom Shipley, a former Special Forces operator turned serial entrepreneur and aggressive investor. Tom challenges the traditional startup narrative with a shocking reality: Growing organically might increase your value by 50% over five years, but buying competitors can increase it by 1,200%. Tom shares his incredible journey from the dot-com bust, where he was days away from missing payroll, to buying a $15M division of Boise Cascade without using his own capital. We unpack the "Programmatic M&A" playbook, how to use acquisitions to solve operational weaknesses, and why the best path to a massive exit is often buying your way there.
--
Tom Shipley is a serial entrepreneur and M&A strategist known for creating the “Add a Zero” growth philosophy, which helps founders rapidly scale their businesses through strategic acquisitions. From his early career as an IDF special forces operator to building and advising brands that have generated more than $2 billion in revenue, Tom brings a rare combination of disciplined execution and bold dealmaking. A pioneer of programmatic M&A for mid-market companies, he has raised over $100 million, led multiple acquisition platforms, and now teaches 7 to 9 figure founders how to accelerate growth, close capability gaps, and engineer premium exits through smart, repeatable deals.
Websites - https://www.tshipley.com/
- https://dealconlive.com/
LinkedIn - https://www.linkedin.com/in/t-shipley/
Time Stamps:
00:00 - Intro
02:47 - Buying a division of a Fortune 500 company without cash
05:05 - Scaling a beauty brand from $30k to $100M+ via acquisition
08:09 - How Mezzanine debt works (and why it’s better than pure equity)
12:51 - The Golden Stat: 50% vs. 1,200% Enterprise Value growth
17:58 - The thought exercise that will force you to raise your prices today
20:41 - The biggest mistakes entrepreneurs make when selling
24:14 - Why "Day One" after closing is the most dangerous time
27:31 - What is Programmatic M&A?
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The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
All content for The Exit - Presented By Flippa is the property of The Exit - Presented By Flippa and is served directly from their servers
with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
Are you trying to grow your business by 10% year over year? You might be leaving massive wealth on the table. In this episode, we sit down with Tom Shipley, a former Special Forces operator turned serial entrepreneur and aggressive investor. Tom challenges the traditional startup narrative with a shocking reality: Growing organically might increase your value by 50% over five years, but buying competitors can increase it by 1,200%. Tom shares his incredible journey from the dot-com bust, where he was days away from missing payroll, to buying a $15M division of Boise Cascade without using his own capital. We unpack the "Programmatic M&A" playbook, how to use acquisitions to solve operational weaknesses, and why the best path to a massive exit is often buying your way there.
--
Tom Shipley is a serial entrepreneur and M&A strategist known for creating the “Add a Zero” growth philosophy, which helps founders rapidly scale their businesses through strategic acquisitions. From his early career as an IDF special forces operator to building and advising brands that have generated more than $2 billion in revenue, Tom brings a rare combination of disciplined execution and bold dealmaking. A pioneer of programmatic M&A for mid-market companies, he has raised over $100 million, led multiple acquisition platforms, and now teaches 7 to 9 figure founders how to accelerate growth, close capability gaps, and engineer premium exits through smart, repeatable deals.
Websites - https://www.tshipley.com/
- https://dealconlive.com/
LinkedIn - https://www.linkedin.com/in/t-shipley/
Time Stamps:
00:00 - Intro
02:47 - Buying a division of a Fortune 500 company without cash
05:05 - Scaling a beauty brand from $30k to $100M+ via acquisition
08:09 - How Mezzanine debt works (and why it’s better than pure equity)
12:51 - The Golden Stat: 50% vs. 1,200% Enterprise Value growth
17:58 - The thought exercise that will force you to raise your prices today
20:41 - The biggest mistakes entrepreneurs make when selling
24:14 - Why "Day One" after closing is the most dangerous time
27:31 - What is Programmatic M&A?
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
Battling Cancer, Buying Out a Co-Founder, and The "Napkin Pitch" Strategy with Chelsea Jones
The Exit - Presented By Flippa
30 minutes 16 seconds
4 weeks ago
Battling Cancer, Buying Out a Co-Founder, and The "Napkin Pitch" Strategy with Chelsea Jones
Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
What happens when your business explodes with growth at the exact moment your personal life falls apart?
In this episode, we sit down with Chelsea Jones, co-founder of Sunny Road, to unpack a journey that defines entrepreneurial resilience. From losing her life savings on a failed MLM venture to building a successful agency during the chaos of COVID, Chelsea’s story is a masterclass in pivoting.
We dive deep into the messy reality of agency life, discussing the "dark side" of partnerships, how to navigate a buyout while battling a cancer diagnosis, and the complexities of merging two seven-figure companies. Chelsea also opens up about the "Napkin Pitch" concept and why women entrepreneurs need to stop waiting for perfection and start selling their vision.
If you are an agency owner, an e-commerce founder, or an entrepreneur navigating a transition, this episode offers the blueprint for survival and scale.
In this episode, we cover:
The "Fail Fast" Mentality: Lessons learned from a $5,000 loss and early MLM failure.
The COVID Scale-Up: Going from 5 to 32 employees overnight and the operational debt that followed.
The Buyout & The Battle: How Chelsea bought out her burning-out partner while simultaneously undergoing cancer treatment.
Merging & AI: Navigating a merger between friends and how AI has slashed design fees from six figures to low fives.
The "Napkin Pitch": Why you need to run into the room with your idea before it's fully fleshed out.
Exit Strategy: How to prepare your books and your mindset for a sale long before you're ready to leave.
Key Timestamps:
(00:00) Intro
(01:55) The $5,000 mistake: Learning from early failure
(05:14) Scaling during COVID: Managing rapid growth and team burnout
(07:27) The Crucible: Buying out a partner while fighting cancer
(10:50) Merging companies and the impact of AI on agency pricing
(13:21) How to prepare your financials for a merger or exit
(18:15) When is the right time to sell?
(20:02) The "Napkin Pitch": Overcoming perfectionism in business
(23:38) What Sunny Road does for E-Commerce brands
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Chelsea Jones is a visionary e-commerce leader, Shopify Platinum Partner, and co-founder of Sunny Road. She first built her reputation at Chelsea & Rachel Co., the first women-founded agency to achieve Shopify Premier status, where she created high-performing online stores and became a trusted partner for brands looking to scale. In 2023, she joined forces with Drew Himel of Fireside Digital to launch Sunny Road, a digital agency that blends creative excellence with data-driven growth. Today, Chelsea leads with the same passion and client-first approach that have defined her career, helping brands build e-commerce experiences that shine.
Website - https://sunnyroad.co/
LinkedIn - https://www.linkedin.com/in/chelsea-jones101/
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
The Exit - Presented By Flippa
Want a quick estimate of how much your business is worth?
With our free valuation calculator, answer a few questions about your business, and you’ll get an immediate estimate of the value of your business.
You might be surprised by how much you can get for it: https://flippa.com/exit
--
Are you trying to grow your business by 10% year over year? You might be leaving massive wealth on the table. In this episode, we sit down with Tom Shipley, a former Special Forces operator turned serial entrepreneur and aggressive investor. Tom challenges the traditional startup narrative with a shocking reality: Growing organically might increase your value by 50% over five years, but buying competitors can increase it by 1,200%. Tom shares his incredible journey from the dot-com bust, where he was days away from missing payroll, to buying a $15M division of Boise Cascade without using his own capital. We unpack the "Programmatic M&A" playbook, how to use acquisitions to solve operational weaknesses, and why the best path to a massive exit is often buying your way there.
--
Tom Shipley is a serial entrepreneur and M&A strategist known for creating the “Add a Zero” growth philosophy, which helps founders rapidly scale their businesses through strategic acquisitions. From his early career as an IDF special forces operator to building and advising brands that have generated more than $2 billion in revenue, Tom brings a rare combination of disciplined execution and bold dealmaking. A pioneer of programmatic M&A for mid-market companies, he has raised over $100 million, led multiple acquisition platforms, and now teaches 7 to 9 figure founders how to accelerate growth, close capability gaps, and engineer premium exits through smart, repeatable deals.
Websites - https://www.tshipley.com/
- https://dealconlive.com/
LinkedIn - https://www.linkedin.com/in/t-shipley/
Time Stamps:
00:00 - Intro
02:47 - Buying a division of a Fortune 500 company without cash
05:05 - Scaling a beauty brand from $30k to $100M+ via acquisition
08:09 - How Mezzanine debt works (and why it’s better than pure equity)
12:51 - The Golden Stat: 50% vs. 1,200% Enterprise Value growth
17:58 - The thought exercise that will force you to raise your prices today
20:41 - The biggest mistakes entrepreneurs make when selling
24:14 - Why "Day One" after closing is the most dangerous time
27:31 - What is Programmatic M&A?
--
The Exit—Presented By Flippa: A 30-minute podcast featuring expert entrepreneurs who have been there and done it. The Exit talks to operators who have bought and sold a business. You’ll learn how they did it, why they did it, and get exposure to the world of exits, a world occupied by a small few, but accessible to many. To listen to the podcast or get daily listing updates, click on flippa.com/the-exit-podcast/
