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TBPN · 8 May 2026 · 2h 33m
Intel & Apple, The American Economic Rollercoaster | Brian Chesky, Josh Reeves, Jonathan Neman, Zal Bilimoria
MentionsBrian CheskyJonathan NemanReach
(01:34) - Apple and Intel Reach Chip Deal (10:05) - The American Economic Rollercoaster (27:52) - Timeline Reactions (43:48) - Josh Reeves, CEO and co-founder of Gusto, a company specializing in payroll, benefits, and HR solutions for small businesses, discusses the company's recent… More on the show's page
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TBPN · 10 Apr 2026 · 2h 25m
SpaceX Financials, Chimpanzee Civil War, Ferrari's Brand Legend | Josh Reeves, Prof. Alex Young, Jason Kim, Chad Janis, Jordan Bramble, Andy Dunn
MentionsAndy DunnDavid Geffen
(02:56) - SpaceX Financials (08:26) - 𝕏 Timeline Reactions (15:30) - Chimpanzee Civil War (23:12) - Ferrari's Brand Legend (39:02) - Prof. Alex Young, an Assistant Adjunct Professor in Human Genetics at UCLA's David Geffen School of Medicine, specializes in statistical genetics and… More on the show's page
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TBPN · 27 Aug 2025 · 3h 4m
SpaceX Launch: Deep Dive & Reactions | Josh Reeves, Keller Cliffton, Will Brown, Julia Steinberg, Olivia Moore, Flo Crivello
WithJosh Reeves
MentionsKeller RinaudoKeller Rinaudo Cliffton
(00:11) - SpaceX Launch Reactions (16:35) - History of SpaceX (29:53) - Mature Startups Get Venture-Debt Boost (41:38) - Timeline Reactions (01:28:52) - Josh Reeves, CEO of Gusto, discusses the company's acquisition of Guideline, a retirement benefits provider, to enhance services for… More on the show's page
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Pattern Breakers · 16 Dec 2024 · 39 min
Josh Reeves: How Gusto Took The Pain Out Of Payroll
WithJosh Reeves
MentionsEdward KimTomer London
When Josh Reeves, Tomer London and Edward Kim founded Gusto in 2012, roughly 40 percent of the employers in the United States were still doing their payroll by hand. Thousands of small business owners spent their time reading up on various federal and local tax codes or buried in late-night… More on the show's page
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This Week in Startups · 2 Aug 2024 · 1h 5m
Overcoming SMB Roadblocks: Expert tips from Gusto's Josh Reeves | Episode 1988
WithJosh Reeves
This Week in Startups is brought to you by… Vanta. Compliance and security shouldn't be a deal-breaker for startups to win new business. Vanta makes it easy for companies to get a SOC 2 report fast. TWiST listeners can get $1,000 off for a limited time at https://www.vanta.com/twist OpenPhone.… More on the show's page
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The Logan Bartlett Show · 26 Jul 2024 · 1h 34m
EP 111: How Josh Reeves (CEO, Gusto) Built a $10B Company Serving Small Businesses
WithJosh Reeves
MentionsReach
Josh Reeves has built Gusto into a nearly $10B company with over $500M in ARR, serving small businesses. In our conversation, Josh delves into Gusto’s 13-year journey, sharing insights on how they achieved product-market fit by initially targeting a very narrow niche. He also highlights the tactics…
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Episodes that name Josh Reeves in their description, which is not the same as being on them.
Term Sheet · 7 May 2026 · 38 min
From a Palo Alto Closet to $1 Billion Revenue: How Gusto Cracked Small Business Software | Term Sheet
MentionsJosh Reeves
Approximately nine out of every ten net new jobs in America come from small businesses, yet they shoulder over $81 billion a year in federal paperwork. As more Americans launch their own businesses, the back office is buckling under the weight.In this episode, Josh Reeves, cofounder and CEO of…
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In Depth · 1 Jul 2025 · 55 min
How Gusto built a $9.5 billion company by identifying a burning problem
MentionsFirst Round CapitalWells FargoY CombinatorJosh ReevesTomer London
Tomer London is the co-founder and Chief Product Officer at Gusto, the payroll and people platform used by over 400,000 businesses. He grew up helping run his dad’s clothing store in Israel, an experience that sparked his mission to build better tools for small business owners. After moving to the…
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This Week in Fintech · 22 May 2025 · 38 min
🎧Vanta CEO Christina Cacioppo Live at Newcomer's Breaking The Bank Summit: Turning Compliance Into a Competitive Advantage and Learnings From $0 to $100M ARR
MentionsAnnie LamontEric GlymanJackie ResesJosh ReevesMatt HarrisWilliam Hockey
In today's episode, Ryan Zauk is joined by Christina Cacioppo , Co-Founder & CEO of Vanta . Ryan and Christina recorded this episode live at Newcomer's Breaking the Bank Summit in San Francisco. The Summit was an invite-only, one-day summit for fintech founders, builders, and investors to…
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In Depth · 20 Feb 2025 · 1h 25m
Inside Guideline's mission to modernize 401(k)s | Building from first principles, finding strategic edges, and rewiring retirement | Kevin Busque (Co-founder and CEO)
MentionsAydin SenkutFidelityJohn ZimmerJosh Reeves
Kevin Busque is the co-founder and CEO of Guideline, a 401(k) management company revolutionizing the retirement space for small and medium-sized businesses. Prior to Guideline, Kevin co-founded Taskrabbit, where he encountered firsthand the complexity and low participation rates of traditional…
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The Twenty Minute VC · 2 Aug 2019 · 32 min
20VC: Why Passion Is Overrated When It Comes To Starting Companies, Why VC Is Overrated As A Financing Mechanism & Why You Should Never Sell Your Company with Waseem Daher, Founder & CEO @ Pilot
MentionsWaseem DaherJohn CollisonPaul EnglishFrederic KerrestJosh Reeves
Waseem Daher is the Founder and CEO @ Pilot , the startup that takes care of your bookkeeping from start to finish so you can focus 100% on making your business succeed. To date, Waseem has raised over $58m in funding from some of the very best firms and people in the business including Index,… More on the show's page
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