Build Mode

Investors want founders who understand the financial reality of their business. Messy data, misunderstood metrics, or waiting until you’re nearly out of cash to start fundraising can cost founders leverage, valuation, and even a term sheet.

In this episode of Build Mode, host Isabelle Johannesen sits down with Sasha Orloff, founder and CEO of Puzzle and Startup Battlefield alum, to talk about what he’s learned from building companies that have raised more than $1 billion collectively.

Sasha breaks down what investors look for during fundraising, which financial metrics founders should know by heart, and why VCs don’t expect your startup to be perfect—they expect you to understand its reality. He also shares how he nearly lost a term sheet because his data room wasn’t ready, how fundraising diligence changes as a startup grows, and why getting your financial house in order can help founders raise with more confidence and leverage.

They get into:

What raising more than $1 billion across multiple companies taught Sasha about fundraising

Why investors value founders who have a strong grasp of their company’s financial reality

The financial metrics founders should know before pitching VCs

How investor expectations change from pre-seed and seed through Series A, B, and beyond

Why revenue growth and the quality of that revenue are critical fundraising metrics

How runway, margins, sales efficiency, and profitability factor into investor decisions

Why waiting until you’re running out of cash can hurt your fundraising leverage

How Sasha nearly lost a term sheet because his data room wasn’t ready

Why financial organization and compliance can influence investor confidence and startup valuations

What founders should have prepared for the due diligence process

Why VCs don’t expect perfection—and why being honest about what isn’t working can make for a stronger pitch

How Sasha’s own fundraising and finance frustrations ultimately led him to build Puzzle

How AI could change the way startups manage accounting and understand their financial health

Subscribe to Build Mode on Apple Podcasts, Spotify, or wherever you like to listen. And watch the full videos on YouTube. New episodes of Build Mode drop every Thursday.

Chapters:

00:00 – Why VCs Want Founders Who Understand Reality

01:26 – Sasha Orloff’s Journey to Building Puzzle

05:05 – Why Puzzle Started With Startup Founders

08:38 – What Founders Should Know Before Fundraising

11:08 – What Investors Look for During Due Diligence

14:37 – Understanding the Financial Health of Your Startup

17:52 – The Financial Mistakes Founders Make

20:19 – When Startups Need Accountants and Finance Teams

24:04 – How Sasha Almost Lost a Term Sheet

26:10 – The Financial Metrics Founders Should Know Cold

28:20 – Lessons From Raising $1B+ Across Multiple Companies

31:45 – Why Financial Readiness Matters to Investors

33:49 – How AI Is Changing Startup Accounting

37:17 – Inside Puzzle’s Series A With General Catalyst

38:52 – Launching Puzzle at Startup Battlefield

40:38 – Sasha’s Advice for Early-Stage Founders

Hosted by Isabelle Johannesen. Produced and edited by Maggie Nye. Audience development led by Morgan Little. Special thanks to the Foundry and Cheddar video teams.

Immigrant founders have built some of the world’s most valuable companies, but many still face barriers that make it harder to get a startup off the ground. Visa restrictions, limited access to friends-and-family capital, shallow networks, and a venture industry built around pattern matching can keep promising founders from getting funded before they have a chance to prove themselves.

In this episode of Build Mode, host Isabelle Johannesen sits down with Manan Mehta, co-founder and managing partner of Unshackled Ventures, to talk about why he believes immigrant founders represent one of venture capital’s biggest overlooked opportunities. Manan breaks down how Unshackled built an investment model designed to help founders navigate immigration barriers, why traditional VC pattern matching causes investors to miss potential outliers, and how his team evaluates founders at day zero—often before they have a product, customers, or traction. He also explains why the structural gaps that make some founders harder to fund may be exactly where investors should be looking for outsized returns.

They get into:

The four structural barriers immigrant founders face when starting companies in the U.S.

How Unshackled Ventures helps founders navigate visas while building their startups

Why VC’s reliance on pattern matching can cause investors to miss outlier founders

How Manan evaluates founders before they have a product, customers, or traction

The IQ, AQ, EQ, and SQ framework Unshackled uses to evaluate founder potential

Why resilience, lived experience, and a founder’s relationship to the problem can matter more than a polished pitch

Why structural gaps can create some of the biggest opportunities for investors

How founders without traditional networks can find alternative paths to early capital

Why founders should understand their personal “why” instead of trying to fit the traditional VC mold

Subscribe to Build Mode on Apple Podcasts, Spotify, or wherever you like to listen. And watch the full videos on YouTube. New episodes of Build Mode drop every Thursday.

Chapters:

00:00 – Why VCs Miss Outlier Founders

01:45 – Why Manan Mehta Founded Unshackled Ventures

04:15 – The Problem With VC Pattern Matching

06:15 – The Friends-and-Family Gap for Immigrant Founders

08:18 – How Unshackled Helps Founders Navigate Visas

10:40 – Building a Startup in Today’s Immigration Environment

12:19 – Solving One of Unshackled’s Hardest Immigration Cases

14:39 – What the U.S. Stands to Lose16:59 – Raising Unshackled’s First Venture Funds

19:40 – Can You Start a Company on an H-1B Visa?

22:13 – How to Evaluate a Founder at Day Zero

28:30 – Measuring IQ, AQ, EQ, and SQ

30:26 – How Fear Drives VC Pattern Matching

33:01 – Why Structural Gaps Create Outlier Opportunities

35:14 – Finding Startup Capital Outside Traditional VC

38:09 – Why Founders Need to Understand Their “Why”

Hosted by Isabelle Johannesen. Produced and edited by Maggie Nye. Audience development led by Morgan Little. Special thanks to the Foundry and Cheddar video teams.

Setting up a sound legal foundation could be what saves a startup down the line. A missing founder vesting agreement, an unclear IP agreement, or a messy cap table can derail fundraising, spark co-founder disputes, or even kill an otherwise promising company before it has a chance to scale.

In this episode of Build Mode, host Isabelle Johannesen sits down with Kristina Subbotinai, founder and CEO of Lesxy and former startup attorney at Cooley, to break down the legal fundamentals every founder needs to get right. Kristina shares the four non-negotiable legal decisions every startup should make from day one, what investors actually look for during due diligence, how founders should think about negotiating control versus valuation, and why leverage is the key to getting better fundraising terms. She also shares real stories from the front lines of startup law, from co-founder breakups and investor negotiations to a founder who tried using ChatGPT to draft a merger agreement.

They get into:

The four legal mistakes that can make a startup unfundable

How founder vesting, IP assignment, Delaware incorporation, and 83(b) elections protect your company

What VCs actually look for during due diligence and how to avoid common red flags

How founders should negotiate valuation, board control, and investor rights

Why leverage comes from building a great business—not signing better term sheets

The wildest legal horror stories Kristina has seen, including a startup acquisition gone completely off the rails

Subscribe to Build Mode on⁠ Apple Podcasts⁠, ⁠Spotify⁠, or⁠ wherever you like to listen⁠. And watch the full videos on⁠ YouTube⁠. New episodes of ⁠Build Mode⁠ drop every Thursday.

Chapters:00:00 – Intro: The Legal Mistakes That Kill Startups01:37 – Why Kristina built Lexsy03:58 – The Legal Foundations Every Startup Needs08:22 – How to Find the Right Startup Lawyer10:21 – The Four Non-Negotiable Legal Decisions17:33 – What Investors Look for During Due Diligence20:04 – SAFE Notes vs. Priced Rounds22:18 – Negotiating Valuation Without Losing Control25:25 – Board Seats, Investor Rights, and Hidden Term Sheet Traps30:51 – Should Founders Use AI for Legal Advice?31:04 – How Founders Build Leverage in Fundraising35:48 – The Terms That Can Destroy Founder Wealth37:01 – The Craziest Startup Legal Story Kristina Has Ever Seen

Hosted by Isabelle Johannessen. Produced and edited by Maggie Nye. Audience development led by Morgan Little. Special thanks to the Foundry and Cheddar video teams.

SeatGeek didn't become one of the biggest names in ticketing by following the playbook. It started as a simple ticket search engine on the TechCrunch 50 stage (now known as TechCrunch Battlefield) and took on the industry’s massive incumbents by expanding its vision, surviving industry-defining challenges, and convincing investors that even a monopoly could be disrupted.

In this episode of Build Mode, host and Startup Battlefield lead Isabelle Johannesen sits down with Jack Groetzinger, co-founder and CEO of SeatGeek, to unpack the company's 17-year journey from startup to industry leader. Jack shares how SeatGeek raised nearly $400 million in venture capital, why he believes founders should think about expanding rather than pivoting, what it was like fundraising during the COVID-19 shutdown of live events, and why the company ultimately walked away from its planned SPAC. He also explains how founders can convince investors to back them against an entrenched incumbent, why your first hires define your company's future, and how AI is reshaping the future of live entertainment and ticketing.

They get into:

Why SeatGeek chose to compete with Ticketmaster and how investors evaluated that opportunity

How SeatGeek survived COVID and closed its hardest fundraising round during the pandemic

Why passionate customers can become your best fundraising asset

The hiring mistakes Jack wishes he could undo and why your first employees shape company culture

How AI is transforming ticketing, live entertainment, and the fan experience

Jack Groetzinger's advice for founders building companies that challenge established incumbents

Subscribe to Build Mode on⁠ Apple Podcasts⁠, ⁠Spotify⁠, or⁠ wherever you like to listen⁠. And watch the full videos on⁠ YouTube⁠. New episodes of ⁠Build Mode⁠ drop every Thursday.

Chapters:

00:00 – Intro: How SeatGeek Took on Ticketmaster

01:09 – From Startup Battlefield to Building SeatGeek

04:03 – Finding Product-Market Fit in a Broken Ticketing Industry

05:54 – Why SeatGeek Expanded Instead of Pivoting

07:14 – Raising Nearly $400M and Surviving the Hardest Fundraise During COVID

10:46 – Why SeatGeek Walked Away from Its SPAC IPO

13:57 – How to Raise Money Against a Monopoly Like Ticketmaster

17:02 – The Hiring Mistakes That Nearly Hurt SeatGeek's Culture

19:08 – How AI Will Transform Live Entertainment and Ticketing

22:19 – Regulation, Competition, and Jack Groetzinger's Advice for Founders

Hosted by Isabelle Johannessen. Produced and edited by Maggie Nye. Audience development led by Morgan Little. Special thanks to the Foundry and Cheddar video teams.

Building a great product is one thing. Getting a company like Nvidia to put its name behind it is something else entirely.

In this episode of Build Mode, host and Startup Battlefield lead Isabelle Johannesen sits down with Sydney Sykes, who leads global venture capital alliances and partnerships at Nvidia, to unpack how startups break into the Nvidia ecosystem and what a corporate venture capital partnership actually looks like once they're in.

Sydney explains how founders can get on Nvidia's radar through programs like Nvidia Inception, why strategic alignment matters more than a slick pitch deck, and how corporate venture capital differs from traditional venture capital when it comes to fundraising, diligence, and deal terms. Drawing on her experience as an investor at NEA and Lightspeed Venture Partners, and as co-founder of BLCK VC, she also discusses access and representation in venture capital and how the AI boom is reshaping who gets funded. She closes with practical fundraising advice for founders hoping to build lasting relationships with corporate VCs like Nvidia.

They get into:

How a startup can "enter the Nvidia orbit" through the Nvidia Inception program

What Nvidia looks for before offering its stamp of approval to an AI startup

Corporate venture capital vs. traditional venture capital: what founders need to know

Why a corporate VC checks for strategic relevance, not just financial upside

How to pitch the same startup differently to a corporate VC vs. an institutional VC

Why founders should build their cap table like a puzzle, not a popularity contest

How the AI boom is lowering barriers to entrepreneurship — and where old barriers remain

Why Sydney believes VCs should pay closer attention to energy and data center infrastructure

How Black VC is expanding access and education across the venture capital industry

Sydney Sykes' advice for founders trying to break into the corporate venture ecosystem

Subscribe to Build Mode on⁠ Apple Podcasts⁠, ⁠Spotify⁠, or⁠ wherever you like to listen⁠. And watch the full videos on⁠ YouTube⁠. New episodes of ⁠Build Mode⁠ drop every Thursday.

Chapters:

00:00 – Intro: How Startups Enter Nvidia's Orbit

01:20 – Meet Sydney Sykes: From NEA to Lightspeed to Nvidia

03:18 – What Sydney Does as Nvidia's VC Alliances Lead

04:20 – The AI Trends Nvidia Is Watching Across Verticals

07:47 – How Startups Can Enter the Nvidia Orbit

10:34 – What Nvidia's "Stamp of Approval" Actually Looks Like

12:56 – How Startups Get Noticed by Corporates (Beyond Nvidia)

15:18 – Does a Corporate Stamp Move VCs to Write Checks?

19:41 – Access, Black VC, and Gatekeeping in Venture Capital

30:20 – Procurement vs. Corporate VC vs. Traditional VC, Explained

38:28 – Final Advice for Founders Chasing Corporate Partnerships

Hosted by Isabelle Johannessen. Produced and edited by Maggie Nye. Audience development led by Morgan Little. Special thanks to the Foundry and Cheddar video teams.