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

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/

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)

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

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.

Host Ben Elowitz sits down with seasoned entrepreneur and fundraising expert Evan Kaplan, CEO and founder of InfluxData, and industry veteran with over $400M raised and three decades of experience across public and private companies.

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.

In this episode of Raiser's Edge, host Ben Elowitz dives deep into the realities of startup fundraising with guest David Shim, CEO and co-founder of Placed and Read.ai,

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.

How do top founders actually raise venture capital—and what do investors really look for?

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.

In this episode, host Ben Elowitz sits down with master fundraiser Dan Shapiro, currently the co-founder of CEO of Glowforge, and the author of Hot Seat: The Startup CEO Guidebook.

From his early days building laser light shows to raising over $200M (and counting) over his startups, Dan reveals how he’s raised capital at every stage by putting data—and his audience—at the center of his strategy. Dan shares his playbook for testing, iterating, and fine-tuning every pitch, using feedback loops, A/B testing, and relentless curiosity to turn rejections into actionable insights. You'll also get tactical advice on getting sincere feedback, building a narrative that resonates with investors while staying true to your mission, understanding founder market fit, and how to keep going when the going gets tough.

For more from Ben, subscribe to our Substack at https://substack.com/@elowitz