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:

What No One Tells You Before Getting Acquired | Scott Tilton Oct 16, 2024

Show notes

Hookit was acquired by KORE Software for much more than the $20 million they raised over three funding rounds.

But getting there was no walk in the park.

In this episode of High Stakes, K Street Managing Partner Paige Soya is joined by Scott Tilton, exited co-founder of Hookit.

They discuss:

• how Hookit got acquired for 2x the offer price

• why co-founders need to be aligned before the big close

• embracing the shift to becoming an employee after a merger

Connect with us here:

1. Scott Tilton: https://www.linkedin.com/in/tiltcore/

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

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

The Strategic Rationale Behind Early Exits | Aaron Mendes & PrivacyHawk Sep 26, 2024

Show notes

Managing our digital footprints has become almost impossible without the right tech.

Personal data is more vulnerable than ever, and cybercriminals are ready to take advantage.

That’s where PrivacyHawk steps in — your defense against this growing digital chaos.

We're thrilled to have backed PrivacyHawk in its recent $3M funding round.

In this conversation with Aaron Mendez, CEO of PrivacyHawk, we discuss everything from dead weight on your cap table, the need for a better understanding of liquidation preferences, and why you're better off selling early rather than too late.

Connect with us here:

1. Aaron Mendes: https://www.linkedin.com/in/mendes/

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

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

M&A Lessons Every Entrepreneur Needs To Know | Richard Leggett & Tom McCormick Sep 12, 2024

Show notes

Building a company for exit? Prepare for the long haul.

In this encore episode, hosted by Paige Soya, Richard Leggett, former CEO of FrontierView, and lead investor Tom McCormick dive into the harsh realities of the world of M&A.

They share how they navigated the pressures of competing priorities, kept the business afloat during the pandemic, and avoided a fire sale by strategically positioning for a successful exit.

With candid insights on resilience, timing, and critical decision-making, this episode is a must-watch for entrepreneurs facing tough choices.

Note: This episode is a re-upload with added substance and a quick sneak peak into the conversation at the start. Enjoy!

3 Exit Strategies That Changed Everything, Featuring Zach Axelrod Aug 29, 2024

Show notes

In this episode of High Stakes, host Paige Soya dives in with Zach Axelrod, CEO of Redball Energy, uncovering the game-changing moments that shaped his entrepreneurial success. Discover:

• How financial leverage and perfect timing led to Zach's career-defining $100M exit

• Insider tips on maximizing returns from high-growth investments

• Crucial lessons on negotiation power dynamics and maintaining control

Zach's candid insights on market timing, profit-taking, and strategic flexibility are pure gold. Don't miss this masterclass in entrepreneurial wisdom!

How This Entrepreneur Sold His Startup To Dropbox For $165M | Russ Heddleston Aug 15, 2024

Show notes

Imagine thinking your startup is doomed, only to be acquired for $165M.

On this episode of High Stakes, Russ Hiddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox.

In this chat with Managing Partner Paige Soya, they discuss funding, exits, Russ’s next venture, Distill (hint: think Wikipedia but for company and people summaries).

Proactive Investment Exit Strategies: Insights from Marcus Brauchli Aug 01, 2024

Show notes

In episode 12 of High Stakes, Paige Soya, Managing Director of K Street Capital, interviews Marcus Brauchli, co-founder of North Base Media and former managing editor at the Wall Street Journal, on the intricacies of investment exits. Marcus shares his extensive experience in the venture capital world, highlighting the lessons learned from both successful and failed exits. They cover the wide range of stories Marcus has to share on the importance of legal documentation, the complexities of international investments, and the various exit strategies companies may face. Marcus also emphasizes the necessity for founders to plan for exits from the beginning and maintain open communication with investors. Tune in for insightful advice on navigating the unpredictable landscape of venture capital exits.

Industry Dive's Expansion Strategy and Exit with Founder Sean Griffey Jul 18, 2024

Show notes

In Episode 11 of High Stakes, Paige Soya interviews Sean Griffey, CEO of Industry Dive. Griffey discusses Industry Dive's journey from bootstrap beginnings to a company with $100 million in revenue and over 400 employees, culminating in its acquisition by Falfurrias Capital. He emphasizes the importance of preparation and cultural fit in acquisitions. Griffey also shares insights into Industry Dive's subsequent acquisition by Informa in 2022, navigating the transition from private equity ownership to being part of a large public corporation, and the opportunities and challenges it brought.

Building Impactful Companies: Insights for Founders, Featuring Joe Fluet Jul 05, 2024

Show notes

In episode 10 of High Stakes, Paige Soya, Managing Partner at K Street Capital, and Joe Fluet, Founder of Fluet Law Firm and MAG Aerospace, discuss Fluet’s journey from founding MAG to navigating significant exits and recaps. He emphasizes a values-driven approach to business, discussing how aligning with investors who share these values is crucial for long-term success. Tune in to hear Fluet’s insights underscoring the complexity and critical decisions involved in building lasting, impactful companies.

Insights on IPOs and acquisitions from both sides of the table, featuring Martin Tobias Jun 20, 2024

Show notes

Join us as we dive into the world of multiple exits with Martin Tobias, Managing Partner of Incisive Ventures. Martin brings a wealth of experience and perspective as a GP and a three-time venture-funded CEO who has navigated IPOs and strategic acquisitions, sharing insights from his journey with Loud Eye Technologies, among others. He discusses the nuances of laddering and IPO pricing, the challenges of lock-up periods, and strategies for managing concentrated positions post-exit. Tune in to Martin and Paige’s discussion on the dynamics of modern exit strategies and valuable perspectives for both founders and investors.

From Campaigns to Companies: Navigating Exits and Venture Capital, featuring Sara Fagen Jun 06, 2024

Show notes

Political operative turned tech entrepreneur, Sara Fagen, shares a wealth of knowledge in this episode of High Stakes. Join us as Sarah and host Paige Soya discuss lessons from raising venture capital, timing an exit, the dynamics of venture-backed versus self-funded businesses, and strategic reasons behind acquisitions in the tech industry. Throughout the conversation, Sarah reflects on the realities of building and exiting successful tech companies.

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