Do What you Say and Say What You Do with Evan Kaplan

Trust is a Long Game with Tushar Garg

Tushar Garg raised over $200M for Flyhomes — one round closed in 30 minutes, another nearly collapsed while his co-founder was hospitalized after being hit by a drunk driver. 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/ [https://www.linkedin.com/in/elowitz/] Follow Raiser's Edge on Substack: https://substack.com/@elowitz [https://substack.com/@elowitz]

Conviction, Courage, and Capital with Stefan Kalb

In this episode of Raiser’s Edge, host Ben Elowitz sits down with Stefan Kalb—entrepreneur, investor, and three-time founder, currently building Super Labs, an AI startup focused on transforming how Main Street businesses operate. 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 [https://substack.com/@elowitz]

Using Story as Strategy with David Politis

Most founders think they have a strategy problem. In reality, they have a storytelling problem. 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/ [https://www.notanotherceo.com/] Follow Raiser's Edge on Substack: https://substack.com/@elowitz [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)

Evolution Over Ego with Omar Tawakol

In this episode, host Ben Elowitz sits down with serial entrepreneur Omar Tawakol, whose journey spans building and leading companies like BlueKai, Voicea, and Rembrandt, as well as strategic acquisitions by industry giants like Cisco and Oracle. 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

Fundraising at Full Throttle with Greg Mark

On this episode of Raiser’s Edge, Ben Elowitz sits down with Greg Mark, CEO and founder of Markforged and Backflip. Drawing on his experience raising over $550M in capital, Greg Mark breaks down what it really takes to capture investor interest and thrive under intense fundraising pressure. 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.