Season 2 Fundraising Demystified Podcast - YouTube

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Season 2 Fundraising Demystified Podcast $100M Exits - w/ Jason Kirby

$100M Exits - w/ Jason Kirby3.76K subscribers

$100M Exits Podcast The podcast that uncovers the untold stories of founders who have weathered the highs and lows of raising capital. Each week, we go beyond the headlines and Techcrunch funding news articles to explore the uncharted territories of the fundraising landscape with a new guest. Don't forget to subscribe for weekly reminders every time a new episode goes live! Join 12K+ founders & investors who open these emails every week

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EP 114 | What Founders Get Wrong After Making Millions From an Exit

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EP 114 | What Founders Get Wrong After Making Millions From an Exit

04/30/2026

EP 113: The Truth About “Free” Investor Money

04/16/2026

EP 112: How He Built and Sold a $100M Startup Twice | Dan Rosenberg

04/11/2026

EP 111: How Defense Tech Startups Get Funded | AI, Warfare, and Venture Capital with Brad Harrison @ Scout Ventures | EP 111

04/02/2026

EP 110: From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital

03/27/2026

EP 109: Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah

03/19/2026

EP 108: Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit

03/05/2026

1:01:08

EP 107: He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree

02/26/2026

1:01:03

EP 106: How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap

02/19/2026

EP 105: From CEO to Employee: The Hardest Pivot of a Founder’s Career

02/12/2026

EP 104: The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar

01/29/2026

EP 103: Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque

01/22/2026

EP 102: He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems

01/15/2026

EP 101: Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai)

12/11/2025

EP 100: The Earnout Trap: What This Founder Learned After Selling His Company

12/04/2025

EP 99: From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit

11/27/2025

EP 98: How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets

11/20/2025

EP 97: From Startup Burnout to $100M Raise: Ron Reiter’s Redemption

11/13/2025

EP 96: Inside the War Room: How to Manage a Company Crisis w/ David Meadvin

11/06/2025

EP 95: How to Sell Your Startup: The Founder’s M&A Playbook

10/30/2025

1:03:33

EP 94: I Bet My Entire Net Worth on Life360 — It Paid $8B Later

10/23/2025

1:07:39

EP 93: Building Europe’s Palantir: How Max Buchan Raised $20M to Launch Valarian

10/16/2025

EP 92: Why I Left My $500M Startup to Start Again — Shay Levi (Unframe AI)

10/10/2025

1:01:17

EP 91: How She Bought Back Her Company From Investors

10/02/2025

EP 90: Search Funds Demystified: How Jon Staenberg (Agate Hound Fund) Nets 35% Annual Returns

06/19/2025

EP 89: From Uber to Snap to AI: Ben Chiang on Raising Millions Then vs Now

06/12/2025

EP 88: How a Broken Leave Policy Led to a $30M HR Tech Startup w/ Jenniffer Henderson (Tilt)

06/05/2025

EP 87: Customer Retention Over Acquisition? Travis Steffen, Who’s Done $200M in Deals, Says Yes

05/29/2025

1:05:21

EP 86: What Founders Get Wrong About Exits (and How John Rood Got It Right)

05/22/2025

EP 85: From Burnout to Breakout: How Jennifer Tsai Bootstrapped Shoott.com to $10M After Raising $2.7M

05/15/2025

EP 84: David Connors Used The Swarm to Raise Millions | Deal Flow, M&A, and Warm Intros

05/08/2025

EP 83: Jess Loren on Digital Twins & Unconventional Strategies of Raising Capital as Female Founder

05/01/2025

EP 82: How to Build a Startup Advisors | Barry Stamos of Supernova on Scaling & Managing Advisors

04/17/2025

EP 81: IPO Market Trends 2025: Best Time to Go Public w/ Peter Goldstein | IPO Valuation & Readiness

04/10/2025

EP 80: JC Glancy’s Unicorn Startup ZenBusiness From Credit Card Debt, Gave Up CEO, Hit $1B Valuation

04/03/2025

EP 79: How to Attract Influencers to Promote Your Startup: Celebrity Marketing & Influencer Deals Explained

03/27/2025

EP 78: How to Make a Startup Successful, Founder Mindset & Startup Operations with Adam Spector of Chore

03/20/2025

EP 77: How To Spot Massive Early-Stage Startup Trends With Katelyn Donnelly Of Avalanche VC

03/13/2025

EP 76: What VC Look For in Early Stage Startups with Dave Lambert Right Side Capital Management

03/06/2025

EP 75: Raising Capital & Selling a Startup for Millions – Jeremy Parker’s Swag.com Story

02/27/2025

EP 74: Jon Tucker of HelpFlow on AI for business efficiency and Evaluating AI Performance

02/20/2025

EP 73: Fundraising Quadrants Explained: Where Does Your Startup Fit?

02/13/2025

EP 72: Bootstrapping, Exiting, and Alternative Fundraising with Laurits Just

02/06/2025

EP 71: How Rebel Energy Scaled £1.5M to £100M with Penelope Hope

01/30/2025

EP 70: From Founder to Philanthropist: $1.3B Deployed by David Goldberg

01/23/2025

EP 69: Scaling and Selling to Eight-Figure Exits with Carrie Kerpen

01/16/2025

EP 68: From Bootstrapping to an Eight-Figure Exit with Conor Tomkies

01/09/2025

EP 67: From Bootstrapping to $175M Exits with David Hauser

12/19/2024

EP 66: How Patrick Butler Built 3 Wildly Different Businesses

12/12/2024

EP 65: Navigating Debt Financing for Startups with Kyle Rector of Boundless

12/05/2024

Season 2 Recap: The Best Fundraising Stories of This Season

12/02/2024

EP 64: From Student Housing Startup to Africa’s Largest Platform with DigsConnect's Alexandria Procter

11/21/2024

EP 63: Using Donor-Advised Funds to Power Underrepresented Startups with Patrice King-Brickman

11/14/2024

EP 62: How to Gracefully Exit Your Startup with Simple Closure's Dori Yona

11/07/2024

EP 61: Interplay's Mark Peter Davis Busts the Biggest VC Myths

10/31/2024

EP 60: From Bootstrapping to Venture Capital to $30M Exits

10/24/2024

EP 59: Master the 12-Month Plan That Will Get You Funded Faster

10/17/2024

EP 58: From Air Force Mechanic to $25M Fintech Founder with Edrizio De La Cruz

10/10/2024

EP 57: Mastering the First Investor Call with Jason Kirby

10/03/2024

EP 56: Hidden Dangers of SAFE Agreements with Massive VC's Ari Newman

09/26/2024

EP 55: Why Noah Friedman of Top Shelf Ventures Thinks Alcohol and Vices Are the Next Big Thing

09/19/2024

EP 54: Mastering AI Startups and Fundraising Tips with Plutoshift's Prateek Joshi

08/15/2024

EP 53: How Michael Markesbery turned NASA Tech into an Insulation Empire and Raised $50 Million in Capital

08/08/2024

Ep 52: When to Sell To Your Business, Exit Strategies and Selling Your Marketing Agency By David Rodnitzky

08/01/2024

EP 51: How Aakash Shah Raised Millions for Wyndly Without Traditional Funding

07/25/2024

EP 50: How Dan Reich Cracked the Code to Multiple Successful Exits

07/18/2024

EP 49: How Chris Gladwin Raised Over $100M and Achieved Over A Billion Dollar Exit Guest Name: Chris Gladwin

07/11/2024

EP 48: How Alex Pattis Raised $75M in 300 Deals by Launching a Syndicate

07/04/2024

EP 47: How Wen-Wen Lam Sold Her $100M Revenue Startup During Covid and Became a Top VC

06/27/2024

EP 46: From Bankruptcy to Multi-Million Dollar Exits with Rob Hunter

06/20/2024

1:01:17

EP 45: This Ex-Lawyer Raised $12M for a Cannabis-Tech Startup and Sold It!

06/13/2024

EP 44: Mastering Venture Capital Strategies with Winter Mead

06/06/2024

EP 43: Solo Founder Diana Heldfond of Parallel Raises $29 Million in Edtech

05/30/2024

EP 42: IPO Expert Peter Goldstein Explains How to Successfully Go Public

05/23/2024

EP 41: From DotCom Failure to Successful Exits, Now A Top Investor

05/09/2024

EP 40: How Brady Nolan's Cold LinkedIn Message Leads to Best Egg's Acquisition of Till

05/02/2024

EP 39: Sim Desai is Shaking Up Secondary Markets with $4.25M in Fresh Capital

04/25/2024

EP 38: How OpenStock is Revolutionizing Private Stock Liquidity with Alex Simpson

04/18/2024

EP 37: How Sherry Jiang Led Bluejay Finance Through a Major Pivot to Success

04/11/2024

EP 36: Proof's Thanasis Delistathis Reveals Strategies to $350M in Venture Capital Investments

04/04/2024

EP 35: From Pro-E-Gamer to CEO, Nick Cuomo Tells How He Raised 12M Series A for AllStar.gg!

03/28/2024

EP 34: Alon Talmor is a "Crises-Time" Founder Raising $20M in a Down Market After Losing his COO

03/21/2024

Ep. 33: How Tyler Denk Built the Newsletter Platform, Beehiiv, to Reach $7M in ARR

03/14/2024

Ep. 32: How Jeremy Vaughan Raised a $3M Seed Round in Cybersecurity for Start Left Security

03/07/2024

Ep. 31: Immigrant Entrepreneur Raised $12 Million for EdTech Startup: Vlada Lotkina of ClassTag

02/29/2024

Ep. 30: How to Find the Right Chief Technical Officer for Your Startup and How a Service-Based Company Got $3 Million Funding with Frank Licea of Howdy.com

02/22/2024

Ep. 29: Get Funded Fast with Kaustav Das’ Revenue-Based Financing Strategies

02/15/2024

Ep. 28: How Nami Baral Raised $7 Million in 2 Weeks for Niural

02/08/2024

Ep. 27: The Secret Weapon to Successful Fundraising: Practical Empathy

02/01/2024

Ep 26: First-time Founder Ryan Eisenman Raised $20 Million in Series A by Building a Robust Network

01/25/2024

EP. 25 How Did Ali Ansari Raise $14 Million in Pre-seed through Proper Positioning and Transparency

01/18/2024

Ep 24: Unlocking the Power of PR in Fundraising with Jordan Bantista

11/14/2023

Ep 23: How Julia Pimsleur Raised $6 Million in Venture Capital and Empowered Women Entrepreneurs

11/07/2023

Ep 22: Zach Bell: Turning a Blank Check into $6 Million Pre-Revenue Funding

11/07/2023

Ep 21: How Jack Hamrick Raised a $3 Million Seed Round For a Specialty Foods Marketplace

10/31/2023

Ep 20: From Survival Mode to Profitable Growth: Bootstrapping Done Differently with Melissa Kwan

10/17/2023

Ep 19: Raising $250 Million Since 1998: Proven Fundraising Tactics and Tips with Nick Desai

10/10/2023

Ep18: From Failures to $10 Million Revenue: How Lloyed Lobo Started Boast.ai From Bootstrapping, Raised $123 in Equity And Debt

10/03/2023

Ep17: From Refugee to Revolutionizing Antibiotic Resistance Detection: The Journey of How Mustafa Al-Adhami Raised $2 Million for Astek Diagnostics

09/26/2023

Ep16: Quaid Walker Raises $8M From VCs & Celebrities Like Kevin Hart for Luxury Watch Marketplace

09/19/2023

Ep15- Raising Capital Before the Crypto Collapse: Lessons from Courtyard.io Founder Nicolas le Jeune

09/12/2023

Ep14: Closing a $3.5 Million Series A Funding: How Unit One Pivoted Their Product Strategy Amidst The Pandemic

09/05/2023

Ep.13- Cultivating Hype and Attention to Raise Capital Successfully with Michael Houck

08/29/2023

Ep - 12 He Raised $20 million For His Startup - Eziah Zaidi, CEO, Mend Labs

08/21/2023

Ep - 11 He Raised $16 MILLION for his Startup 💰 - Nik Talreja, CEO, Sydecar

08/14/2023

Ep - 10 They closed their Series A within 3 MONTHS!! - George Richardson, CEO, AeroCloud

08/07/2023

Ep - 9 What is Venture-Market Fit? - Jens Neuse, Founder, WunderGraph

07/31/2023

Ep - 8 Should you raise VC or bootstrap? - David Daneshgar, CEO, Whippy

07/24/2023

Ep - 7 He raised $4.2 Million for his startup - Brandon Peterson, CEO, Geokey

07/17/2023

Ep - 6 He raised $21 Million for his startup - Brett Martin, Co-founder, Kumospace

07/10/2023

Ep - 5 He raised $2 Million using a picture of a unicorn drawn by his daughter - Martins Lasmanis, CEO, Supliful

07/04/2023

Ep - 4 He raised $48 Million💰 for his estate-planning startup - Daniel Goldstein, COO, Trust & Will

06/27/2023

Ep- 3 Father-Son duo raise $2.5 Million Seed Round solely through warm intros - Romil Verma, CEO, Outdefine

06/20/2023

Ep-2 She raised $12 Million in Series A funding - Caitlyn Krebs, Co-founder, Nalu Bio

06/13/2023

Ep-1 He raised an oversubscribed Series A of $11 Million - Jeff Beck, Co-founder, AnswersNow

06/13/2023

Ep-0 Fundraising Demystified: Podcast Introduction by Jason Kirby

06/13/2023

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$100M Exits - w/ Jason Kirby

•3.7K Subscribers•628 Videos•225K Views

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• Podcast

48:02](https://www.youtube.com/watch?v=tlsLKH1whK4 "The Truth About “Free” Investor Money | EP 113")

The Truth About “Free” Investor Money | EP 113

4/16/2026

46:49](https://www.youtube.com/watch?v=JC5706ukqfQ "How He Built and Sold a $100M Startup Twice | Dan Rosenberg | EP 112")

How He Built and Sold a $100M Startup Twice | Dan Rosenberg | EP 112

4/11/2026

53:27](https://www.youtube.com/watch?v=lSysEyi_soU "How Defense Tech Startups Get Funded | AI, Warfare & VC w/ Brad Harrison @ Scout Ventures | EP 111")

How Defense Tech Startups Get Funded | AI, Warfare & VC w/ Brad Harrison @ Scout Ventures | EP 111

4/2/2026

54:55](https://www.youtube.com/watch?v=bwBHxvvP620 "From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital | EP 110")

From Operator to Investor: George Alifragis on Scaling With Non-Dilutive Capital | EP 110

3/27/2026

59:58](https://www.youtube.com/watch?v=pRlD7YzYeE8 "Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah | EP 109")

Why Silicon Valley Founders Are Panicking About AI w/ Jessica Mah | EP 109

3/19/2026

01:01:09](https://www.youtube.com/watch?v=52yZGMaARno "Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit | EP 108")

Luxury DTC Founder Chris Wichert: Raising $20M, Surviving DTC Collapse & Turnaround Exit | EP 108

3/5/2026

01:01:04](https://www.youtube.com/watch?v=rH9PUgilLaw "He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree | EP 107")

He Pivoted to Survive—Then Sold to Victoria's Secret for ~$700M | Brian Ree | EP 107

2/26/2026

54:55](https://www.youtube.com/watch?v=eAHF8e-TigU "How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap | EP 106")

How Sendoso Raised $100M From SoftBank w/ Kris Rudeegraap | EP 106

2/19/2026

38:24](https://www.youtube.com/watch?v=05Ntx6TUXRc "From CEO to Employee: The Hardest Pivot of a Founder’s Career | EP 105")

From CEO to Employee: The Hardest Pivot of a Founder’s Career | EP 105

2/12/2026

48:32](https://www.youtube.com/watch?v=fx5bJ7eKShA "The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar | EP 104")

The Psychology Driving Fundraising, VC Decisions, and Founder Failure w/ Aram Attar | EP 104

1/29/2026

59:00](https://www.youtube.com/watch?v=q1OmQ-Rq-9g "Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque | EP 103")

Built a $100M Software Business at 22 | Matthew Wyatt, Founder of TechTorque | EP 103

1/22/2026

46:25](https://www.youtube.com/watch?v=Occ1vXCAVTA "He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems | EP 102")

He Raised $76M With No Defense Tech Background | Nelson Mills Founder of VATN Systems | EP 102

1/15/2026

55:38](https://www.youtube.com/watch?v=bXlSlk4zCF8 "Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai) | EP 101")

Unicorn Founder Raises $8M Using AI (Andrew D’Souza, Clearco & Bordy.ai) | EP 101

12/11/2025

44:47](https://www.youtube.com/watch?v=1DDkOd_POVs "The Earnout Trap: What This Founder Learned After Selling His Company | EP 100")

The Earnout Trap: What This Founder Learned After Selling His Company | EP 100

12/4/2025

59:52](https://www.youtube.com/watch?v=xM7JyaAF7D4 "From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit | EP 99")

From Zero to $10B in Secondaries: Greg Brogger 's Journey to a $160M Exit | EP 99

11/27/2025

53:33](https://www.youtube.com/watch?v=qiu7q8MymUg "How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets | EP 98")

How Andrew Ackerman Scaled DreamIt Ventures & Made 70+ Startup Bets | EP 98

11/20/2025

58:23](https://www.youtube.com/watch?v=yaL5XCgFmzY "From Startup Burnout to $100M Raise: Ron Reiter’s Redemption | EP 97")

From Startup Burnout to $100M Raise: Ron Reiter’s Redemption | EP 97

11/13/2025

55:18](https://www.youtube.com/watch?v=99ovoRfIzp0 "Inside the War Room: How to Manage a Company Crisis w/ David Meadvin | EP 96")

Inside the War Room: How to Manage a Company Crisis w/ David Meadvin | EP 96

11/6/2025

01:03:34](https://www.youtube.com/watch?v=AAKIoJvRr0w "How to Sell Your Startup: The Founder’s M&A Playbook | EP 95")

How to Sell Your Startup: The Founder’s M&A Playbook | EP 95

10/30/2025

01:07:40](https://www.youtube.com/watch?v=5f3DSAET2UU "I Bet My Entire Net Worth on Life360 — It Paid $8B Later | EP 94")

I Bet My Entire Net Worth on Life360 — It Paid $8B Later | EP 94

10/23/2025

41:42](https://www.youtube.com/watch?v=JPxeDuhVjLQ "Building Europe’s Palantir: How Max Buchan Raised $20M to Launch Valarian | EP 93")

Building Europe’s Palantir: How Max Buchan Raised $20M to Launch Valarian | EP 93

10/16/2025

00:05](https://www.youtube.com/watch?v=zfIUgFTKO5g "$100M Exits with Jason Kirby")

$100M Exits with Jason Kirby

10/1/2025

01:44](https://www.youtube.com/watch?v=UcYBn3vVoYg "It's Time For a Change")

It's Time For a Change

9/30/2025

54:03](https://www.youtube.com/watch?v=5dUCPko9dhk "I Bought Back My Company from VCs — Here’s What Really Happened | EP 91")

I Bought Back My Company from VCs — Here’s What Really Happened | EP 91

10/2/2025

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