Episodes

  • It's All About You/It's Not All About You
    Jun 26 2025

    In this episode, Heidi discusses how founders tend to swing between two extremes — thinking it's not all about them (when actually, it is), or believing it's only about them and their company (when it really isn't). She'll review both sides and point out what founders often get wrong — and how to get it right.

    More information: https://www.threshold.vc/podcast

    Further reading:

    On the occasion of our 40th episode, here are the names and links to the 'village' of people responsible for making this podcast a reality!

    My partners at Threshold: https://threshold.vc/team

    Carol Wentworth, my creative partner for all 40 episodes: https://www.linkedin.com/in/cawentworth/

    Producer/Director Nick van der Kolk: https://loveandradio.org/

    Forrest Lawrence/Working Title Recording Studio: https://workingtitlerecordingstudios.com/

    Albertson Design for original concept, production, and creative artwork: https://albertsondesign.com/

    Music composer Brad Wells: https://www.roomfulofteeth.org/bios/brad-wells

    And thanks to our own Wendy McArdle, who manages distribution

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    11 mins
  • Inside the Black Box of VC Behavior
    May 22 2025

    While the internal dynamics of a VC firm may feel like a black box, you can often infer what's going on based on how your VC is acting – if you know what to look for. In this episode, Heidi explains why many VC behaviors that seem confusing or inconsistent can make more sense once you understand the inner workings of venture funds and firms.

    More information: https://www.threshold.vc/podcast/inside-the-black-box-of-vc-behavior

    Further reading:

    • Here's a good post about when preferred converts to common, including in an IPO, as I brought up in this episode: https://www.startupventureadvisors.com/when-should-preferred-stock-be-automatically-converted-into-common-stock#:~:text=When%20a%20startup%20goes%20public,a%20minimum%20aggregate%20offering%20amount.
    • Here's a short but sweet summary of how VC carry works: https://www.angellist.com/learn/carried-interest
    • Mark Suster has written some great material on understanding venture capital. His post on crossover investments will help you understand why VCs don't tend to do them: https://bothsidesofthetable.com/can-vc-s-invest-across-two-funds-5ee7313808e7
    • Here's a link to my own prior episode about recaps: https://threshold.vc/podcast/the-case-of-the-radical-recap/
    • And finally, I've linked to it before, and I'll keep doing it – here's a link to Evan Epstein's great breakdown of private company governance to share with your VC if they are putting their own interests ahead of the company in your board meetings: https://evan-epstein.medium.com/duties-of-startup-directors-and-the-rule-of-common-maximization-9a2814b2fe2a
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    18 mins
  • Understanding Your Investor's Zone of Indifference
    Apr 24 2025

    Founders need to understand investor priorities before they require investor action. The investor's 'zone of indifference' describes an issue that can be problematic. In this episode, Heidi explains what it is, when it comes into play, and how to identify the likelihood of an investor landing in the 'zone of indifference.'

    More information: https://www.threshold.vc/podcast/understanding-your-investorrsquos-zone-of-indifference

    Further reading:

    • As promised, here's a post written by Evan Epstein about fiduciary duties of venture-backed directors. It's a must read! https://evan-epstein.medium.com/duties-of-startup-directors-and-the-rule-of-common-maximization-9a2814b2fe2a
    • And if you want to go deep on the seminal case on this topic, the Trados case, here's an in-depth podcast about it with Evan and Vice Chancellor J. Travis Laster of the Delaware court: https://boardroom-governance.com/episodes/travis-laster
    • Here's a great primer on preferred stock: https://darroweverett.com/preferred-stock-primer-value-protective-provisions-analysis/#:~:text=Preferred%20stock%20sits%20between%20debt,liquidation%20events%20and%20dividend%20payouts"
    • Here's a breakdown of simple preferred versus participating preferred and how it impacts the zone of indifference: https://veecee.co/understanding-liquidation-preferences-and-the-zone-of-indifference
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    18 mins
  • The Art of the Cold Email
    Mar 20 2025

    Mastering cold emails is a superpower—one that can unlock dream investors, top-tier hires, and world-class mentors. The most successful founders craft messages that break through the noise and create opportunities. In this episode, Heidi shares the proven strategies she teaches at the Stanford Graduate School of Business to help you master the art of impactful outreach.

    More information: https://www.threshold.vc/podcast/the-art-of-the-cold-email

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    20 mins
  • The Case of the Elusive Earnout
    Feb 21 2025

    If you're considering an earnout, you should know exactly what is involved to set expectations – and to give yourself the highest chance of it amounting to something. Heidi presents recent market data along with her firsthand experience to help you understand why earnouts are so challenging.

    More information: https://www.threshold.vc/podcast/the-case-of-the-elusive-earnout

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    20 mins
  • How to be a Great Mentee
    Jan 23 2025

    Successful entrepreneurs seek out mentors to positively impact their careers. But how do they find a mentor, initiate contact, and build a relationship? As an experienced mentor and mentee, Heidi believes all these questions can be answered by following her tips on becoming a great mentee.

    More Information: https://www.threshold.vc/podcast/how-to-be-a-great-mentee

    Further Reading:

    I mentioned a bunch of organizations and resources in this episode, so here are the links to them:

    • Fortune Brainstorm and other conferences: https://fortune.com/conferences
    • TechCrunch Disrupt and other events: https://techcrunch.com/events
    • Meetup Entrepreneurship groups: https://www.meetup.com/topics/entrepreneurship
    • Startup Grind: https://about.startupgrind.com
    • Founder Institute: https://fi.co
    • Indie Hackers: https://www.indiehackers.com
    • LinkedIn groups for entrepreneurs: https://www.linkedin.com/pulse/16-linkedin-groups-entrepreneurs-gs-kumar-job-search-trainer
    • Techstars: https://www.techstars.com/communities
    • Founders Network: https://foundersnetwork.com
    • Reddit entrepreneurs subgroups: https://startupsavant.com/startup-center/best-subreddits-for-entrepreneurs and https://startupsavant.com/startup-center/best-subreddits-for-entrepreneurs

    And finally, here are first-person narratives on learning how to be interested, not interesting. There are similarities – but there's something to learn in each one of them:

    • https://www.jodymichael.com/blog/be-interested-not-interesting
    • https://tybennett.com/be-interested-not-interesting
    • https://www.jackysherman.com/networking-the-art-of-being-interested-not-interesting
    • https://sunwords.com/2024/01/28/dont-be-interesting-be-interested
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    18 mins
  • The Case of the Venture Debt Dilemma
    Jan 9 2025

    All entrepreneurs should understand what venture debt is so they can make an informed decision to take it or not. Heidi poses a series of questions and scenarios to help founders know whether it's a good option for their company. And if it is, how to set it up and use it.

    More Information: https://www.threshold.vc/podcast/the-case-of-the-venture-debt-dilemma

    Further Reading:

    • As I mentioned in the episode, General Catalyst has an interesting offering around a financing model for growth equity that is a hybrid of debt and equity: https://www.generalcatalyst.com/stories/the-unbundling-of-growth-equity
    • Also, as mentioned, the next version of the SAFE has arrived in the form of a SAFERloan agreement, which allows for some repayment instead of conversion: https://www.liquiditygroup.com/resource-funding/what-is-the-safer-agreement
    • Here's a solid primer on debt covenants:https://www.lightercapital.com/blog/what-are-debt-covenants-on-a-loan#:~:text=A%20debt%20covenant%20lays%20out,more%20specific%20and%20complex%20requirements
    • Finally, one thing I didn't cover in the episode but is relevant to the decision-making about debt is that the lender may ask you to move all your banking business to their bank. And that can prove disastrous in situations like what happened to SVB. Here's a great piece on that danger: https://www.linkedin.com/pulse/wake-svbs-collapse-some-tech-founders-turn-against-venture-tanya-dua
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    20 mins
  • The Best Entrepreneurs are Great at Business
    Dec 5 2024

    Many entrepreneurs start companies to solve a big problem or apply innovative technology, or both. But when they fail, it's typically the result of a business issue. Heidi has observed that founders usually run out of money because they didn't pay close enough attention to running the company. Here, she shares practical advice to help entrepreneurs become great at business.

    More information: https://www.threshold.vc/podcast/the-best-entrepreneurs-are-great-at-business

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    19 mins