High Stakes

Paige Soya

5,0 (7)
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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.

ВЫПУСК 1

Fundraising from VCs: Game Changing Insider Tips | Basel Fakhoury

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

43 мин.
ВЫПУСК 2

How Government Policy Shapes VC-Backed Startups: Lessons from Softbank | Bruce Andrews

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: Bruce Andrews on LinkedInSoftBank GroupGambling Man'Blackstone’s Byron Wien Discusses Lessons Learned in His First 80 Years'Stay at Risk and Live Forever: Lessons from a Life of Curiosity, Grit, and ReinventionPaige Soya on LinkedInK Street CapitalK Street Capital on Youtube

35 мин.
ВЫПУСК 3

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

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.

56 мин.
ВЫПУСК 4

Why Some VCs Lead and Others Don’t | Mark Volchek

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.

42 мин.
ВЫПУСК 5

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

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.

39 мин.
ВЫПУСК 6

The Cold, Hard Truth About Startup Shutdowns | Dori Yona

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 SimpleClosureHidden liabilities and risks founders and VCs often missWhat happens to intellectual property, equity, and employee obligationsData from 2023–2024: which startups are shutting down, where, and whyThe surprising prevalence of founder-led shutdownsVisa challenges for international founders during closuresHow SimpleClosure streamlines the wind-down processThe role of VCs in helping founders exit cleanly and move forwardWhether 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.

42 мин.
ВЫПУСК 7

Landing a job in VC | Myrto Lalacos

In this episode of High Stakes, host Paige Soya sits down with Myrto Lalacos, Principal at VC Lab, for an in-depth conversation on landing a job in VC. Myrto shares her unique career journey—from leading accelerator programs in the UK to co-founding a B2B SaaS fund and launching the Venture Institute, an initiative aimed at connecting diverse, emerging talent with pathways into VC. Together, Paige and Myrto explore what it really takes to be a fund manager, and the often-overlooked skills critical to running a venture firm—not just sourcing deals.What You'll Learn in This Episode: ● How Venture Institute is reshaping VC education to cultivate tomorrow’s top investors ● Why deep roots in the startup ecosystem aren't just helpful—they’re your unfair advantage ● Myrto’s bold leap from accelerator programs to deploying capital ● The incredible story of a candidate who coded their way into a VC role ● What sets Venture Institute’s analyst training apart ● The fundraising muscle every fund manager must build Whether you’re an aspiring investor, curious about breaking into VC, or want to understand how new funds are formed, this episode is packed with real world insights and inspiration. #startups #venturecapital #careerventurecapitalist #VC #VCLab

36 мин.
ВЫПУСК 8

Habits of Highly Successful Founders | Alex Wirth, CEO of Quorum

What separates successful founders from the rest? In this episode of High Stakes, Paige Soya (Managing Partner, K Street Capital) sits down with Alex Wirth, CEO & Co-founder of Quorum, to unpack the habits, mindsets, and leadership lessons that helped him scale his company from 2 founders to 300+ employees over 10 years. Key takeaways: ✅ How to build the right team at every stage of growth ✅ When founders need to evolve their leadership style ✅ The role of mindset and resilience in navigating startup highs & lows ✅ Lessons on scaling without overextending your cash flow Whether you’re a VC or an operator, this conversation is packed with timeless advice.

40 мин.
ВЫПУСК 9

The Unseen Work of Venture Capital | James Barila, Executive Director of Station, DC

There’s a lot to love about working in venture capital but there’s also a lot of hard, often overlooked work that doesn’t make the headlines. In this debut episode of High Stakes, Paige Soya, Managing Partner at K Street Capital, sits down with James Barila, Former Revolution VC investor, now Executive Director at Station DC, for a candid conversation about the realities of running a venture fund – beyond sourcing deals. They unpack the not-so-glamorous core responsibilities of a VC that don’t get the headlines they deserve but keep a firm alive. The episode also explores why emerging managers need to be setting up a DC ground game strategy early. For founders in tech and innovation-driven sectors, engaging with the Washington ecosystem is not optional. Proximity, presence, and participation can be the difference between momentum and missed opportunities. Whether you're an emerging manager, a founder navigating policy, or an LP curious about what happens behind the scenes, this episode offers a clear-eyed look at the unglamorous – but essential – side of venture.

38 мин.
ВЫПУСК 10

Why VCs Care About Board Seats | Brian Goldsmith, Co-founder & Partner at Avenue Growth Partners

Ever wonder why venture capitalists fight for board seats? It's not just about control or fancy dinners. In this episode, Paige Soya (Managing Partner, K Street Capital) sits down with Brian Goldsmith (Managing Partner, Avenue Growth Partners) to pull back the curtain on board governance in venture capital. In this episode, they cover the real work behind board seats, share war stories from boardrooms and explain why the right board can literally save companies from bankruptcy. Moving beyond the quarterly meeting stereotype, Paige and Brian dive into the substantial work that happens between board meetings. They discuss how effective board members provide ongoing strategic support, help founders navigate cash flow crises before they become critical, and serve as trusted advisors during the inevitable ups and downs of startup life. The conversation explores the real motivations behind VC board seat requirements, moving beyond simple control narratives. Brian explains how board seats enable better value creation through ongoing visibility and trust-building. He also discusses how they provide necessary governance rights to protect LP interests. They discuss the delicate balance between serving as a fiduciary to the fund while remaining a supportive partner to founders, especially when these interests might appear to conflict.

42 мин.
ВЫПУСК 11

Dual Threat CEOs

At K Street, we’ve had the privilege of backing some incredible founders and over time, one theme has become increasingly clear: The most impactful leaders aren’t just building great companies, they’re also investing in others. These are dual threat CEOs: founders who play both offense and defense. They're scaling their own ventures while also writing early checks, mentoring rising entrepreneurs, and giving back to the ecosystem that helped them succeed. In the latest episode of High Stakes, K Street investor Sara Fagen joined Paige Soya to unpack what that role really looks like and why it matters. She shared a powerful perspective on how investing can be a vehicle for impact especially for new founders who have big ideas but lack access or experience. These early-stage bets often start with a conversation, a relationship, and a belief that someone just needs their first chance. That’s the ethos we carry at K Street. We back operators who pay it forward and we’re proud to count so many dual threat CEOs in our portfolio and community.

38 мин.

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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.

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Paige Soya
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52
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3
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High Stakes

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18 авг.