High Stakes

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Podcast by Paige Soya

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

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07 November 2024

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

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

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29:38

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24 October 2024

Leverage IP For A Winning Exit | Todd Bracher & Paige Soya

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

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25:13

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16 October 2024

What No One Tells You Before Getting Acquired | Scott Tilton

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/

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42:13

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26 September 2024

The Strategic Rationale Behind Early Exits | Aaron Mendes & PrivacyHawk

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/

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45:40

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12 September 2024

M&A Lessons Every Entrepreneur Needs To Know | Richard Leggett & Tom McCormick

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!

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43:00

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29 August 2024

3 Exit Strategies That Changed Everything, Featuring Zach Axelrod

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!

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25:30