✨Startups & VC Investing Demystified✨ New episodes Monday & Thursday!
Chicago, IL
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Is seed becoming the new sucker round?
@thejohnchen of @fikavc joins TFR to discuss $10–15M pre-seed rounds, fear and greed in AI, VC “kingmakers,” soaring valuations, why the best product can still win, and where he’s finding overlooked opportunities.
Link in bio.
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Building technology is getting easier. Building a great company is not.
@vsvaidya of @supersetstudio joins TFR to discuss AI cost structures, pricing, proprietary data moats, choosing the right problem to solve, and why execution may be the ultimate moat. Ep 516 link in bio.
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AI isn't killing software. It's killing companies without barriers.
In episode 514, @mpd explains why AI is expanding demand, how @interplay built an internal AI system that boosted productivity by 50%, and why venture investors need a new playbook for finding winners.
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The biggest wealth creation in tech now happens before IPO. @benjamindblack explains why he launched @PWRL_ to give investors exposure to companies like @SpaceX, @OpenAI, @stripe, @databricks, and @perplexity_ai—and why he believes the traditional 10-year VC fund model is broken.
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What creates the most combat power: ships, munitions, or AI software?
@TFR_Pod Producer Brenna Kyper guest hosted her @WestPoint_USMA classmate @DemareeGrant, CEO of @Onebriefapp ($2B+). They discuss AI, defense tech, founder mode, and the future of military planning.
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What happens when software stops being a tool & starts doing the whole job? I sat down with Jake Saper of Emergence Capital to discuss AI-native services, outcome-based pricing, trust as a moat, & why SaaS is being rethought. Episode 506 is brought to you by @dottechdomains.
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Investors share the deals that got away.
Why did VCs pass on Solana, Zoom, Twilio, and MongoDB?
Featuring @AriannaSimpson of @a16z, @NavinChaddha of @MayfieldFund, and @ethanaustin of Outside VC on the painful lessons behind billion-dollar anti-portfolios.
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What makes a truly visionary founder?
@JTananbaum of @ForesiteCapital, @mkhandel of @defyvc, and @davidcohen of @Techstars share stories of exceptional founders they’ve worked with—and the traits that separate them from the rest. Brought to you by @dottechdomains.
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Fintech isn’t an inning — it’s an evergreen evolution.
I sat down with Eric Byunn of @CentanaGrowth to discuss 25 years of fintech cycles, growth investing, monopoly myths, identity + fraud, and today’s AI-driven expectations.
Episode 503 is live now - link in bio.
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In Why I Passed, Paul Madera of @MeritechCapital, @bussgang of @flybridge, and Victor Orlovski of @R136Ventures share the real stories behind passing on @netflix, @PalantirTech, and @VeevaSystems—and the lessons that still shape how they invest. #VentureCapital #Startups
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Being wrong 80–90% of the time isn’t a failure — it’s the job. @jcal7 of @trueventures explains why curiosity, not certainty, drives great venture outcomes, and how long-term thinking and repeat founders shape True’s approach. Episode 501 of The Full Ratchet.
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Episode 500 is live. 500 conversations, countless lessons.
For this milestone episode of The Full Ratchet, Benjamin Orthlieb of @BlueMoon_VC joins me to break down AI-native venture and what’s next for VC. Link in bio.
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What separates a good founder from a true 100x founder?
@bussgang of @flybridge, @thedatavc of @645ventures, and @chudson of @PrecursorVC break down how their investing philosophies have evolved—and why, at the earliest stages, people now matter far more than markets.
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What happens when Facebook builds your product and wipes out eight years of work? Founder-turned-investor @ethanaustin shares how that journey led to Outside VC, backing outsider founders in fintech and climate. Full episode now live on The Full Ratchet.
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Shamin Walsh of @BAMVentures, @aniehenke of @scalevp, and @aaref of @BainCapVC share stories of working with leaders like @smakani (@Motive_inc), @t_xu (@DoorDash), @patrickc (@Stripe), and @Keller (Zipline)—from deep customer obsession to elite recruiting and relentless focus.
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AI is moving in dog years.
I sat down with @Redpoint MD @jacobeffron to talk models vs agents, vertical AI in healthcare and legal, why “T2D3 is dead,” and where the real defensibility will come from in AI apps and tooling.
The link to TFR and Episode 496 is in our bio.
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How do great investors evolve?
@kyork20 of @YorkGrowth, @someshdash of @IVP, and Paul Madera of @MeritechCapital share how their philosophies have changed — from early angel bets to disciplined diligence and deeper listening.
Check out Investor Stories 439 today. Link in bio.
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“Banks will be fully automated—with zero employees.” Victor Orlovski of @R136Ventures joins TFR to discuss DPI without IPOs, late-stage growth traps, why people still trump metrics, and how agentic AI is reshaping fintech and banking. Check out Episode 495 today. Link in bio.
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