20VC Newsletter - 26th October 2025
Venture Capital

20VC Newsletter - 26th October 2025

Harry Stebbings
Harry StebbingsOct 26, 2025

Summary

Here are the transcripts and top takeaways from 20VC episodes released this last week.

20VC Newsletter - 26th October 2025

20VC Newsletter · 26 October 2025

Here are the transcripts and top takeaways from 20VC episodes released this last week.


Monday’s episode with Alex Bouaziz, Co‑Founder & CEO @ Deel

Takeaways

  1. How to Get Value From VC Meetings When You Are Not Fundraising

    I only take meetings with investors if there are meaningful outcomes, like 2–3 potential customer introductions. There’s value for you and value for me. If I can get a bit more value, it’s even better.

  2. Companies Need to Make Their Own Tailored Software and We Made Our Own Jira

    A lot of SaaS are not tailored enough for us. We built our own Jira to speed up ticket management. It’s the dumbest thing to do if you’re small, but the smartest thing you could do as you scale.

  3. The Two Types of Acquisitions That Deel Does

    Core market: We buy the team & revenue, bring them in house, then rip & replace their infrastructure with ours.

    Adjacent market: We rebuild the entire infrastructure from the ground up.

  4. How Deel Ramp New Acquisitions So Fast

    Post‑acquisition timeline:

    • Month 1‑2 – Rebuild all frontend inside Deel while backend remains connected to the current company.

    • Month 3‑12 – Rebuild full backend depending on scale.

    In parallel: migrate existing customers, start selling the new product, fix bugs, and close product gaps. We can reach product scale in 9 months while others take 24.

  5. Biggest Lesson From Failed M&A

    The acquisitions that did not work out were ones where we said “Why not?” instead of “Hell yeah.” They were usually at the end of the line: minimal revenue, adjacent enough to be relevant but not enough for me to care.

  6. Do Richer Founders Make Better Founders

    Getting rich mid‑journey can hurt execution if you don’t manage it. A lot of founders get distracted once they’ve made a decent amount of money. They need to set boundaries early so money doesn’t derail focus or company momentum.


Thursday’s episode with Rory O’Driscoll, GP @ Scale, and Jason Lemkin, Founder @ SaaStr

Takeaways

  1. Everyone Is in Market for New Tools and It Is Not Sustainable

    The AI hype is pushing every buyer in‑market at once. Firms are approving $50K–$150K+ budgets to buy tools. Everyone is in the market instead of the usual 5 % like in traditional SaaS. It’s like 2021 again: this is not sustainable and the window will close.

  2. When Customers Choose a Vendor They Do Not Change; Be the First and Run Like Hell

    Business process change is expensive. CIOs today say the cost of onboarding new AI apps is at an all‑time high. They will not be doing this every year and likely won’t be in the markets anytime soon.

  3. How to Know When to Sell vs Hold in M&A

    Practical test for any M&A offer:

    • Is TAM growing faster than our revenue?

    • Is our market share still small?

    If yes to both, hold. If TAM is flat or slowing, sell.

  4. Why Today Is Harder Than It Has Ever Been in VC

    The market works, but variance is high and capital is abundant. Investors must take risk far out the curve to compete. The technology is exciting but it is sobering when you sign a check.

  5. Why Spotify Won vs a Bunch of Other Competitors

    All the US‑based competitors were strangled by lawyers at birth. Spotify had friendlier licensing deals in Europe. They got to critical mass early, built a great product, then gradually increased their leverage vs label companies.


Friday’s episode with Sandy Diao, Growth Advisor @ Drift International

Let us know what your big takeaways from this week’s shows were in the comments below!


Upcoming episodes

  • Monday – David Cahn, Partner @ Sequoia Capital

  • Thursday – Jason Lemkin & Rory O’Driscoll

  • Friday – Tim Ferriss, Author, Podcaster & Investor


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