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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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Scott Kelly, founder/CEO of Black Dog Venture Partners, shares 30 years of lessons helping tech and consumer brands fund, sell, and scale.
We dig into why “sales is a lost art,” why your network is your real funding source, and how to build relationships that lead to opportunities.
Plus: keystone habits, outworking 21-year-olds at 61, and why you should love practice as much as the game.
Highlights & Timestamps
- 0:00 Meet Scott Kelly — exits, accelerators, and why he never really “retired”
- 2:42 What success actually looks like (solve problems, create opportunities)
- 4:13 Sweet spot: early-stage tech & CPG; why sales often fixes everything
- 5:00 The lost art of asking for the sale (and handling “no”)
- 6:37 Stop doing $5/hr tasks when you’re paid for $500/hr outcomes
- 8:02 “Wozniak & Jobs” — know your lane; if you can’t sell, hire it
- 8:45 Learn the ratios: leads → calls → closes (practice, not theory)
- 9:55 Investor-readiness: your pitch, story, questions, & live “VC Fast Pitch” reps
- 11:25 Follow-up matters: most wins happen on touches 5–6+
- 11:45 Money is in your list: coffees > cold banks; DM your “couch money”
- 12:24 Daily relationship reps: LinkedIn to real conversations; 100 lunches challenge
- 13:49 Don’t pitch-slap investors on first contact; relationships first
- 13:57 Old school still works: direct mail & handwritten notes that close deals
- 15:26 Keystone habit: “obscene work ethic” — love the grind, love the practice
- 17:29 Parting advice: never stop learning, be confident & humble, don’t give up
Pull Quotes
- “Sales is a lost art. Ask for the money—and be okay hearing ‘no.’”
- “Stop doing $5/hour tasks when you’re paid to produce $500/hour outcomes.”
- “Relationships lead to opportunity. Don’t pitch-slap on the first message.”
- “If you can’t sell, be honest—find someone who can.”
- “Love the practice as much as the game.”
Guest Links
📲 Instagram: https://www.instagram.com/blackdogceo/?hl=en
📲Linked In: https://www.linkedin.com/in/blackdogceo
📲Facebook:https://www.facebook.com/blackdogceo/
🌐 Website: https://blackdogceo.com/
Host Links
- Rodric’s books: Million Dollar Flip Flops and The Magnet, The Method and The Machine
- Send a Student Leader Abroad (SASLA) — 100% of book profits support the mission
Resources:
Ready to transform your business and your life while making a difference? Grab your copy of *Million Dollar Flip Flops*—the ultimate guide to creating a life and business that feels just as good as it looks. And here’s the best part: 100% of the proceeds go directly to our foundation, Send a Student Leader Abroad, with a goal of sending 1,000,000 deserving kids on life-changing trips around the world.
As a thank you for your support, we’re offering exclusive bonuses available only for our podcast listeners. These bonuses are packed with extra tools and resources to help you implement the principles from the book faster and more effectively.
Don’t miss this opportunity to gain invaluable insights, impact a young leader’s life, and be a part of something bigger.
Click the link, order your copy, and claim your listener-only bonuses today!
Together, let’s change lives—one trip at a time.
www.MillionDollarFlipFlops.com/book
**P.S.** Every book you buy gets us one step closer to sending 1,000,000 kids on life-changing adventures. Let’s make it happen!
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