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Ep. 12: Todd Caponi - Journey from Sales Leader to Author, Speaker, and Sales Historian
In this episode of How I Started, host Andrew Kappel interviews Todd Caponi, author of The Transparency Sale and founder of Sales Melon, a sales training and keynote business built around behavioral science and honesty in selling.
Todd shares his unorthodox journey—from tech sales rep to SVP of Sales, to CRO of Chicago’s fastest-growing tech company, and eventually quitting to write a book after a surprising buyer behavior study changed his worldview. He explains how embracing transparency in sales not only feels better but actually improves conversion rates.
Todd also dives into his rollercoaster entrepreneurial experience, why he says “no” often, how he builds self-discipline using quarterly board-style reports, and what inspired his passion project—the Sales History Museum.
Takeaways:
- A Northwestern University study on reviews convinced Todd that honesty converts better than perfection.
- Revealing flaws in your product or service up front can build trust and speed up decision-making.
- After resigning from a high-growth CRO role, Todd had to say no to “can’t-miss” opportunities to stay focused on writing his first book.
- Building a business meant experimenting with consulting, training, and keynotes, and then doubling down on what worked best.
- The entrepreneurial journey is bumpy, with highs and lows—Todd shares how Q1 2024 was his best quarter ever, followed by a slow Q2.
- He conducts solo quarterly reviews (like board meetings) to analyze revenue, buyer demographics, win rates, and business health.
- Learning to qualify leads better saved him time and improved his sales process.
- Todd's new book,Four Levers Negotiating, aims to replace outdated haggling with a cards face-up, trust-based approach.
- The Sales History Museum is a passion project highlighting lost wisdom from 19th- and 20th-century sales books and artifacts.
- His mission: Make sales a trusted, admired profession again.
Chapters:
00:00– Intro & Sales History Museum Welcome
00:57– From Tech Sales Rep to Leadership & Sales Trainer
03:28– Buyer Behavior Study That Changed Everything
06:10– Quitting the CRO Role to Write *The Transparency Sale*
08:21– Saying No: How Mentorship Helped Todd Focus
10:31– Turning Down Salesforce & Finding the Real Lesson
12:35– Building the Business: Experiments, Focus, and Lessons
15:02– Riding the Revenue Rollercoaster as an Entrepreneur
16:51– Doing Board-Style Reviews to Self-Audit the Business
20:02– Qualifying Leads & Understanding Buyer Roles
22:09– Writing *Four Levers Negotiating* & What It Teaches
26:10– What Is the Sales History Museum?
28:38– Hunting Vintage Sales Books & Artifacts
30:10– Closing Thoughts & Where to
Connect with Todd:
Caponi:https://www.linkedin.com/in/toddcaponi/https://www.transparencysale.com/Sales History Podcast:https://podcasts.apple.com/us/podcast/the-sales-history-podcast/id1607151709
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By Andrew KappelIn this episode of How I Started, host Andrew Kappel interviews Todd Caponi, author of The Transparency Sale and founder of Sales Melon, a sales training and keynote business built around behavioral science and honesty in selling.
Todd shares his unorthodox journey—from tech sales rep to SVP of Sales, to CRO of Chicago’s fastest-growing tech company, and eventually quitting to write a book after a surprising buyer behavior study changed his worldview. He explains how embracing transparency in sales not only feels better but actually improves conversion rates.
Todd also dives into his rollercoaster entrepreneurial experience, why he says “no” often, how he builds self-discipline using quarterly board-style reports, and what inspired his passion project—the Sales History Museum.
Takeaways:
- A Northwestern University study on reviews convinced Todd that honesty converts better than perfection.
- Revealing flaws in your product or service up front can build trust and speed up decision-making.
- After resigning from a high-growth CRO role, Todd had to say no to “can’t-miss” opportunities to stay focused on writing his first book.
- Building a business meant experimenting with consulting, training, and keynotes, and then doubling down on what worked best.
- The entrepreneurial journey is bumpy, with highs and lows—Todd shares how Q1 2024 was his best quarter ever, followed by a slow Q2.
- He conducts solo quarterly reviews (like board meetings) to analyze revenue, buyer demographics, win rates, and business health.
- Learning to qualify leads better saved him time and improved his sales process.
- Todd's new book,Four Levers Negotiating, aims to replace outdated haggling with a cards face-up, trust-based approach.
- The Sales History Museum is a passion project highlighting lost wisdom from 19th- and 20th-century sales books and artifacts.
- His mission: Make sales a trusted, admired profession again.
Chapters:
00:00– Intro & Sales History Museum Welcome
00:57– From Tech Sales Rep to Leadership & Sales Trainer
03:28– Buyer Behavior Study That Changed Everything
06:10– Quitting the CRO Role to Write *The Transparency Sale*
08:21– Saying No: How Mentorship Helped Todd Focus
10:31– Turning Down Salesforce & Finding the Real Lesson
12:35– Building the Business: Experiments, Focus, and Lessons
15:02– Riding the Revenue Rollercoaster as an Entrepreneur
16:51– Doing Board-Style Reviews to Self-Audit the Business
20:02– Qualifying Leads & Understanding Buyer Roles
22:09– Writing *Four Levers Negotiating* & What It Teaches
26:10– What Is the Sales History Museum?
28:38– Hunting Vintage Sales Books & Artifacts
30:10– Closing Thoughts & Where to
Connect with Todd:
Caponi:https://www.linkedin.com/in/toddcaponi/https://www.transparencysale.com/Sales History Podcast:https://podcasts.apple.com/us/podcast/the-sales-history-podcast/id1607151709