Business

High Stakes

Join seasoned investors and successful start-up founders as they weigh in on topics and trends currently dominating the venture capital space. Each episode brings together a founder and an investor to provoke a deepened understanding of the topic at hand. If you want to learn about how early-stage venture capital investing works, this show is for you.

Latest Episodes:

The Cold, Hard Truth About Startup Shutdowns | Dori Yona May 22, 2025

Show notes

What really happens when a startup shuts down? In this revealing episode of High Stakes, host Paige Soya sits down with Dori Yona, founder of SimpleClosure and seasoned entrepreneur, to unpack the complex—and often hidden—realities of shutting down a startup. After navigating the painful process of closing his own VC-backed company, Dori realized just how broken and opaque the process was, and became determined to fix it. Now, after guiding over 500 shutdowns in 2024 alone, he brings clarity to a topic most founders and investors would rather avoid. From legal minefields and IP entanglements to payroll risks and emotional tolls, Dori shares what every stakeholder needs to know about ending a startup the right way.Key Points From This Episode:

How Dori’s own shutdown journey inspired the creation of SimpleClosure
Hidden liabilities and risks founders and VCs often miss
What happens to intellectual property, equity, and employee obligations
Data from 2023–2024: which startups are shutting down, where, and why
The surprising prevalence of founder-led shutdowns
Visa challenges for international founders during closures
How SimpleClosure streamlines the wind-down process
The role of VCs in helping founders exit cleanly and move forward

Whether you’re a founder, operator, or investor, this episode is a must-listen for understanding the realities of startup shutdowns—and how to navigate them with integrity.

When Venture Deals Go South: Inside the Realities of Startup Failures, Wind Downs, Write-Offs, and Zombie Companies May 08, 2025

Show notes

Not every startup story ends in a big exit. Sometimes, despite best efforts, companies miss key milestones, burn through their runway, or become what investors call “zombie startups.”

In this episode of High Stakes, host Paige Soya sits down with Tony Chan, partner at ORIC and seasoned venture capital and M&A expert, to explore the hard truths of venture investing. Tony shares insights into what happens when deals go south—and what investors can (and should) do when startups are struggling.

Key Points From This Episode:

• Common examples of how companies can handle early closures and exits.

• The importance of early, honest conversations when things aren’t going to plan.

• Why founder optimism and investor caution can be hard to reconcile.

• Founder trust in VCs: how it hinges on operating experience and credibility.

• Navigating misaligned incentives among early and late-stage investors.

• What really happens behind the scenes before and after a board meeting.

• How disciplined investors avoid FOMO and spot underfunded opportunities.

• Why some startups are turning to even-sided mergers instead of IPOs.

• The growing role of secondaries in private market liquidity.

• How VC is shifting as private equity becomes more accessible to retail investors.

Why Some VCs Lead and Others Don’t | Mark Volchek Apr 24, 2025

Show notes

Why do some VCs lead while others follow? On this episode of High Stakes, host Paige Soya sits down with Mark Volchek, founding partner at Las Olas Venture Capital, to explore the dynamics of leading versus following in venture capital. With a focus on early-stage B2B software, Mark brings insights from his journey, from founding a FinTech company during the dot-com crash to launching and managing multiple successful funds since 2016. Together, they unpack the pros and cons of leading investment rounds, how firm size and resources influence strategy, and how to navigate key decisions like taking board seats, aligning with co-investors, and allocating resources. Mark also shares advice for founders on finding the right VC fit and explains why there is a firm out there for every type of startup. Tune in for a deep dive into how venture firms decide when to lead and when to follow, and what that means for investors and founders alike!

Key Points From This Episode:

• Mark’s journey from entrepreneurship to venture capitalism.

• Lessons from being an angel investor and limited partner (LP).

• The value of being on the board of companies you’ve invested in.

• Key advantages and challenges of leading investments.

• How to take the size and resources of your VC firm into account.

• The difficulties of following on in oversubscribed rounds.

• Unpacking the necessity of aligning with co-investors.

• Mark’s advice to founders on how to find the right VC fit for your company.

Breaking Into Venture—No Straight Paths, Just Bold Moves | Ethan Austin Apr 11, 2025

Show notes

How do you make it in venture capital when the path is anything but straightforward? In this episode of High Stakes, Ethan Austin, Founding Partner at Outside VC, shares his journey and the key lessons he's learned as a founder in the world of early-stage investing. From the importance of empathy and people skills over traditional finance experience to the power of networking and taking bold, unconventional actions to set yourself apart, Ethan breaks down what it takes to succeed in VC. He also reveals why storytelling, strategic name-dropping, and putting your own capital on the line can make all the difference in your career. Whether you're looking to break into the industry or refine your approach, Ethan's insights will help you navigate the highs and lows of venture capital success. Tune in to learn how to leverage relationships, embrace failure, and become a smarter, more resilient investor!

Key Points From This Episode:

• No straight path: a founder’s guide to a career in early-stage venture capital.

• Why empathy and people skills matter more than traditional finance experience.

• The power of networks: how relationships open doors.

• How the best investors assess risk, luck, and opportunity.

• Key traits of successful VCs, including dedication, creativity, and resilience.

• Insight into what it really takes to break into the venture capital world.

• Taking bold, unconventional action to stand out from the crowd.

• The magic of winging it, embracing failure, and just making the leap.

How Government Policy Shapes VC-Backed Startups: Lessons from Softbank | Bruce Andrews Mar 27, 2025

Show notes

When choosing to invest in a company, there are a lot of elements for VCs to consider—and government policy is no exception. Today on High Stakes, we explore the role of government policy in venture capital and its impact on the industry. Joining Paige Soya to break it all down is Bruce Andrews, who has spent the last 30+ years at the intersection of business, public policy, and politics. Over his career, he’s occupied a range of consequential roles, both in government and commerce, from Deputy Secretary of the US Department of Commerce to Vice President for Global Public Policy at SoftBank. Bruce unpacks the ways government policies affect VCs, how a change in administration can impact startups, and what companies should do to prepare. He sheds light on his time at SoftBank and what it taught him about the VC industry before expanding on how the company helped startups by giving them access to government affairs experts. We also hear Bruce’s reflections on failure and success, his advice to listeners, and more. Join us for a fascinating exploration of government policy and its impact on the industry of venture capital!

Key Points From This Episode:

Bruce’s background in government and commerce and his time at SoftBank.
How American policies compare with regulatory approaches in other countries, like China.
Challenges SoftBank successfully navigated when working with the US government.
Predictions for the new administration: potential regulatory changes and their effects.
How SoftBank helped companies by giving them access to a government affairs team.
What Bruce considers his biggest failure in the VC industry and what he learned from it.
Final thoughts from Bruce and the best advice he has ever gotten: “Be nice to everyone.”

Links Mentioned in Today’s Episode:

Fundraising from VCs: Game Changing Insider Tips | Basel Fakhoury Mar 13, 2025

Show notes

What would you do if you spent two years working relentlessly on a startup idea only to realize no one wants it? That’s exactly what happened to Basel Fakhoury before he and his co-founders scrapped their first business and pivoted to User Interviews, a platform that has now raised $45 million in venture capital. In this episode of High Stakes, Paige Soya sits down with Basel to break down what it really takes to raise money from VCs, from navigating rejections to mastering the fundraising narrative. They cover the art of building investor relationships (spoiler alert: it’s a long game!), the must-have data points and deal terms that can make or break a pitch, why a strong financial story matters just as much as traction, and how User Interviews transitioned from a scrappy Craigslist hustle to a SaaS powerhouse. Plus, Basel shares the biggest mistake he made as a founder and the fundraising strategy that changed everything.

Key Points From This Episode:

• Focusing on things you can control: what it takes to raise venture capital.

• What investors actually look for and how to make it easier for them to say yes.

• The psychology behind a VC’s biggest fear (and how to leverage it).

• Why warm introductions and investor networks are crucial.

• Reasons that transparency and consistency are key in VC due diligence.

• Red flags that make term sheets a dealbreaker for founders and funders.

• One thing that VCs really want to know: can you do it again?

Links Mentioned in Today’s Episode:

User Interviews

Basel Fakhoury on LinkedIn

Basel Fakhoury on X

Entrepreneurs Roundtable Accelerator (ERA)

The Lean Startup

Paige Soya

K Street Capital

K Street Capital on YouTube

The End Is Not the End | Greg Vetter Dec 05, 2024

Show notes

In the final episode of Season 2, K Street Capital’s Managing Partner, Paige Soya, sits down with Greg Vetter—the driving force behind Tessemae’s, one of the nation’s most iconic condiment brands.

Greg unpacks the journey of growing a family business into a brand that was valued at $300M+ at its peak. From navigating the fallout of the pandemic to ultimately filing for Chapter 11, his story is one of grit and perseverance.

He also opens up about his new book, “Undressed: The Unfiltered Story of My Failed American Dream and How It Led to Success,” offering a candid look at the lessons learned along the way.

A fitting close to a season all about exits—don’t miss this one.

Greg’s book- https://www.amazon.com/Undressed-Unfiltered-Failed-American-Success/dp/0960127704

Connect with us here:

1. Greg Vetter: https://www.linkedin.com/in/gregvetter/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Why Transparency Can Make or Break a Transaction | Dimitry Gershenson Nov 22, 2024

Show notes

In this episode of High Stakes, Dimitry Gershenson shares how his team tackled the operational and financial diligence required to pull it off, in this conversation K Street Capital’s Managing Partner, Paige Soya.

Dimitry reflects on the challenges of validating key information, noting that diligence often means asking the same question in multiple ways to uncover inconsistencies.

They discuss the importance of trusting your instincts during the diligence process and how open, honest communication can make or break a successful transaction.

Connect with us here:

1. Dimitry Gershenson: https://www.linkedin.com/in/dgershenson/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

How This Georgetown MBA Class Project Got Acquired by GoodBuy Gear | Alli Cavasino & Natalie Poston Nov 07, 2024

Show notes

What started as an MBA class idea led to an acquisition by one of the nation’s leading baby and kid gear marketplaces.

Alli Cavasino and Natalie Poston, founders of JoyLet, built a no-frills “rent-the-runway” model for baby gear, allowing parents to rent items for the time they need.

In EP 19 of High Stakes, Alli and Natalie join Paige Soya, Managing Partner of K Street Capital, to discuss the exit and how they navigated the roadblocks in their journey.

Connect with us here:

1. Alli Cavasino- https://www.linkedin.com/in/allicavasino/

2. Natalie Poston- https://www.linkedin.com/in/natalieposton/

3. Paige Soya: https://www.linkedin.com/in/paigesoya/

4. K Street Capital: https://www.linkedin.com/company/kstreetvc/

00:00 Introduction

00:47 Meet the Founders: Ali and Natalie

01:41 The Birth of Joylette

04:41 Early Challenges and MVP Development

05:38 Raising Capital and Going Full-Time

07:31 Learning and Pivoting the Business Model

09:34 Customer Acquisition Strategies

16:43 Deciding to Exit

19:34 The Exit Process

24:43 Reflections and Future Plans

Leverage IP For A Winning Exit | Todd Bracher & Paige Soya Oct 24, 2024

Show notes

How do you leverage intellectual property for M&A?

In this episode of High Stakes, Todd Bracher joins Paige Soya to answer.

With over 20+ years experience in building great products, Todd believes that the world’s biggest problems already have solutions, but they need the right design approach to shine.

They discuss:

- how better design can give your patent the moat it needs

- TRLs and IP litigation attorneys

- making a product market-ready

Don’t miss out.

Connect with us here:

1. Todd Bracher: https://www.linkedin.com/in/toddbracher/

2. Paige Soya: https://www.linkedin.com/in/paigesoya/

3. K Street Capital: https://www.linkedin.com/company/kstreetvc/

Resources:

1. Design in Context (Todd’s book)- https://www.toddbracher.com/book

2. Market Efficiency Index (Free tool for founders/investors)- https://www.toddbracher.com/mei