Sean is the founder of Flurry (sold to Yahoo, 98% market share at exit) and Outlier.ai (exited 2022), a CEO coach, and the author of the Breaking Point newsletter. In this conversation, he makes the case that fundraising is sales — and that most founders lose not because their pitch is weak, but because they’re pitching the wrong investors and telling the story the wrong way.

In this episode:

• How to research investor bias before your first meeting — who’s predisposed to say yes, who’s already been burned by something adjacent, and who you should skip entirely

• Why you have two minutes at the top of every pitch to earn the room — and what happens if you don’t

• How to end a pitch so investors are still thinking about it at the end of the week

• The friction filter: why making it hard for investors to meet you actually improves your odds

• What makes VCs more risk-averse than they appear — and how to use that to your advantage

• Why fundraising is a full-time 3–6 month commitment, and what happens to founders who treat it as a side project

About Raiser's Edge: 

Raiser's Edge is the podcast where you get the chance to open top fundraisers' playbooks, and get a capital advantage for you and your company. Host Ben Elowitz talks to world-class founders, investors, and operators about what actually works when you’re pitching, closing, and building a venture-backed company. New episodes every other week. Subscribe on YouTube, Spotify, and Apple Podcasts.

Connect with Sean Byrnes:
The Breaking Point: https://breakingpoint.tech
The Startup Help Desk: https://thestartuphelpdesk.com
Find Sean on LinkedIn: https://www.linkedin.com/in/sbyrnes/
 
Follow Raiser’s Edge:
Apple Podcasts: https://podcasts.apple.com/us/podcast/raisers-edge/id1850622699
Spotify: https://open.spotify.com/show/6jUhW3Yq0ZnvBFZnWngnzj?si=5b902a95261e47da
Substack: https://substack.com/@elowitz
Find Ben on LinkedIn: www.linkedin.com/in/elowitz

Tushar is the co-founder and CEO of Flyhomes, a proptech company that pioneered cash-backed offers for homebuyers. In this episode he traces a full decade of fundraising — from a 30-minute seed term sheet through a $150M Series C he didn't plan for, to a near-death survival round raised in a frozen market after cutting more than 80% of the company. Every round traces back to a relationship he had been quietly building for years.

In this episode:

• Why Tushar treats every investor meeting as a long-term relationship — even when they say no
• How he raised Series B while his co-founder was in the hospital and his daughter was in the NICU
• How a $30-50M Series C target became a $150M round — and why he says they raised too much
• The market crash playbook: cutting 80%+ of headcount, managing morale, and staying honest with investors
• How his original seed investor — met a decade earlier — led the survival round that saved Flyhomes
• His core principle: "Trust is your currency" — and what that looks like across a decade of building

Show notes:

00:00 — Intro: The two-minute arc of Flyhomes

02:02 — Tushar's background: Microsoft, Mayo Clinic, and becoming a realtor by accident

06:00 — Seed round: A 30-minute term sheet with Al Goldstein and Mark Vadon

07:11 — Series A: Why they chose Andreessen Horowitz's Alex Rampell over a higher offer

07:20 — Series B: Raising while a co-founder was hospitalized after a drunk-driving accident

09:18 — Series C: Planning for $30-50M, closing $150M with Battery Ventures and Norwest

15:30 — Market crash: Interest rates, revenue collapse, and cutting 80%+ of the team

19:05 — Survival round: Complicated cap table, big pref stack, and the seed investor who stepped up

21:00 — Investor green flags and red flags

23:01 — Relationship vs. transaction: Why Tushar sees no other way

25:12 — Founder advice: Trust is your currency

About Tushar Garg:

Tushar Garg is the co-founder and CEO of Flyhomes, a Seattle-based real estate technology company. He previously held roles at Microsoft, where he was PM for the core Bing search algorithm, and conducted AI and brain research with Mayo Clinic. Flyhomes has raised over $200M in equity financing and pioneered the cash-backed offer model for homebuyers.

About Raiser's Edge:

Raiser's Edge is a podcast for founders and operators navigating venture capital fundraising. Host Ben Elowitz interviews top founders about the real mechanics of raising — the strategies, the failures, the relationships, and the moments that made the difference. New episodes on YouTube, Spotify, and Apple Podcasts.

Connect with Ben: https://www.linkedin.com/in/elowitz/

Follow Raiser's Edge on Substack: https://substack.com/@elowitz

Stefan shares his journey from a shy early founder to a more seasoned, “presidential” CEO, including lessons from building Shelf Engine and raising $8M in preempted funding for his latest company.

They discuss what it really takes to raise venture capital today, including how to identify and win over “kingpin” investors, what separates good founders from exceptional ones, and how to build trust with VCs in competitive markets. The conversation also explores how fundraising is evolving in the age of AI, where speed, adaptability, and conviction matter more than ever.

This episode is packed with practical insights for founders, operators, and investors looking to better understand how great companies get funded—and how to navigate the process more effectively.

Follow Raiser’s Edge on Substack for Ben’s takeaways on every episode: https://substack.com/@elowitz

In this episode of Raiser’s Edge, Ben Elowitz sits down with David Politis, a multi-time founder (Vocalocity, BetterCloud) who has raised over $300M in venture capital, to break down why storytelling is the most important skill in fundraising. 

But this isn’t about clever narratives or polished pitch decks. David explains how great founders use storytelling strategically—to align with what investors are looking for, systematically close risk, and build belief over time. From early mistakes overselling projections to developing a disciplined approach to underpromising and overdelivering, this conversation is a masterclass in turning your company into something investors have to fund.

David also hosts the Not Another CEO Podcast, where he interviews top founders and CEOs about the real, unfiltered journey of building and scaling companies. If you enjoyed this conversation, it’s well worth checking out.

Listen to David's Not Another CEO Podcast: https://www.notanotherceo.com/

Follow Raiser's Edge on Substack: https://substack.com/@elowitz

0:00 – Introductions

2:00 – From Terrified Speaker to $300M Founder 

5:30 – What Makes a Great (and Terrible) Investor

7:00 – Why Storytelling Beats IQ and EQ in Fundraising

10:00 – The Founder Journey: Vocalocity, Cloud Sherpas, BetterCloud

14:30 – Early Fundraising Mistakes (and Artificial FOMO)

17:30 – What VCs Actually Want: The “Fund Maker” Story

22:00 – Using Data to Build a Narrative Investors Believe

27:00 – A Brutal Sequoia Pitch—and the Lesson That Changed Everything

32:00 – How to Create Traction (and Ask Investors the Right Questions)

So what does it really take to fundraise, lead, and build game-changing startups—again and again? Omar shares lessons learned through market crashes, tough boardroom conversations, and high-stakes pivots. He reveals the importance of leveraging feedback as a tool for growth, not just validation, and the unique power of learning from every pitch—success or setback.

If you want unvarnished advice on how and why simplicity, humility, and relentless learning always win—press play.

For more insights from this episode, follow Ben on Substack: https://substack.com/@elowitz

Greg Mark opens up about the rollercoaster world of startups—from the thrill of being the “Ferrari” in a hot round, to the grit required to fundraise when the market turns cold. You'll hear lessons learned from both easy and brutally challenging fundraising cycles, and a masterclass in pitching that turns your company story into a blockbuster movie that investors actually want to watch. Beyond the tactics, Greg Mark goes deep on personal growth, sharing how empathy and appreciation for the people across the table have shaped his journey. 

These are practical, hard-won strategies for founders at any stage - you won’t want to miss access to Greg’s masterful playbook. Tune in for lessons on how to stay in control of your raise without having to take your foot off the gas. 

Evan shares how credibility and authenticity are the keys to successfully raising capital for your startup. He builds relationships with his investors step by step—for him, gaining trust isn’t just words, it’s about maintaining consistency in your process.  

You’ll also hear about some near-death startup moments, the importance of seeing the raise from the VC’s point of view, and how handling setbacks with humility and grit pay off in the long run.

This episode is packed with practical advice and the personal insights you need to build trusting relationships with investors—and survive the inevitable ups and downs of the startup journey.

The episode unpacks the critical importance of designing a business to be fundable—not just following trends—and why storytelling and narrative matter, but great metrics matter more. With stories of pre-emptive term sheets and the struggle of pitching to 100+ investors, this episode offers advice on using your control wisely: build for real customers, craft a compelling story, and understand when timing is everything (and what to do when it’s out of your control).

Whether you're at a hot AI startup or grinding through the “cold” sectors, this candid exchange is packed with practical takeaways on fundraising playbooks, investor psychology, and the necessity of runway. Tune in for real lessons on how to shape your fundraising strategy for what you can control—and adapt for what you can’t.

In this episode of Raiser’s Edge, host Ben Elowitz sits down with serial entrepreneur Russ Fradin (Larridin, Adify, Dynamic Signal) for a candid, unfiltered conversation about the realities of startup fundraising and building a venture-backed company that lasts.

With decades of experience, over $1B raised, and board seats across multiple high-growth startups, Russ shares the fundraising lessons founders can’t afford to learn the hard way.

They break down:

• How to prepare for investor conversations (and avoid the most common founder mistakes)
• Red flags and green flags when choosing VCs
• Why FOMO-driven fundraising backfires
• How honesty, humility, and self-awareness change your outcomes
• What separates the founders who raise successfully from those who stall out

Russ offers practical, plainspoken advice for navigating the emotional roller coaster of raising capital—and staying focused on building a business worth investing in.