20VC interviews Benchmark partner Everett Randle

Good 20VC interview on venture capital investing with Benchmark’s new partner Everett Randle.

Everett has a background from some of the best software/venture investing firms (Vista Equity Partners, Bond, Founders Fund, and Kleiner Perkins) and it was interesting to hear some of his thoughts on how the firms (including their lead partners and culture) are different while the firms all are successful.

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When did you encourage founders to go bigger?

A good interview with Sten Tamikvi of Plural, an European early stage VC fund, in Dragos Novac’s Sunday CET.

Sten’s final question to the readers is good:

“And of course, a question I hope all European investors would ask themselves at least weekly: when was the last time you encouraged your founders to go bigger, bolder, faster, more aggressive than they proposed?”

I believe that the same way lack of ambition (for lack of a better word) make it harder to attract people and capital to a startup, being overly aggressive for aggressiveness sake can backfire even if a startup does attract great people and capital, as it risks premature scaling.

But anyone raising venture capital to finance her startup should aim to go big, that is as important as early product/market fit or early traction.

When to go aggressively big and when to wait a little? That is a question that has a unique answer for every startup.

Current favorite podcast: 20VC’s weekly tech news with Rory O’Driscoll, Jason Lemkin and Harry Stebbings

My favorite podcast for the last few months has been 20VC’s weekly news podcast with Rory O’Driscoll (Scale), Jason Lemkin (SaaStr) and Harry Stebbings (20VC). It is a nerdy and venture-focused take on startup and tech news. In a great ensemble the star of the show is Rory, who in my mind provides the best tech news commentary anywhere at this point.

Strong AI startup funding is not about Sweden but about a few startups

Sifted yesterday reported that the funding of Swedish AI companies so far in 2025 have been €454 million compared to €124 million in 2024.

Of that €445 million has been raised by Lovable and Legora if I read the article correctly. Something looks to be wrong with the data, as that would mean that only €9 million would have been raised by other companies (which is plainly wrong).

However, directionally it seems right. Large amounts of venture/growth capital go into a few breakout startups, like Lovable and Legora, and drown out the steady-state investment level into a range of startups.

So often when a country sees a lot more capital being invested it is not about the country, but about a few specific startups becoming breakout companies.

What startups can learn from Spotify’s quarterly reporting

Spotify reported Q3’25 results yesterday, and while it to some extent was more of the same, it is an impressive read. Passing 700 million monthly active users, closing in on 300 million subscribers (reached 281 million at the end of Q3) and having a 13.6 % operating margin on €4.3 billion in quarterly revenue.

While Spotify is a public company with a $130 billion valuation, startups should be inspired by their investor deck.

  • Spotify manages to make it focused and also consistent from quarter-to-quarter
  • It highlights key metrics across usage, revenue, margins, and cash.
  • Metrics are compared both to guidance (or budget in a startup setting), over time (5 quarters making it possible to compare Q3’25 to Q3’24 and understand year-over-year development), and for some metrics per geography.
  • Margins and revenue are split between the Premium and Advertising segments, which are quite different
  • Comments on each slide make it easier to understand the drivers of metrics
  • Highlights of product and platform releases

Regardless of doing internal, board or investor reporting it is good to have: Focus on key metrics, consistency in reporting to allow comparability, splitting of data to allow deeper analysis, and highlighting impact of product work.

Startup perception and reality

Running a startup is not easy, and it doesn’t get mentally easier when one sees peers and competitors fundraising at high valuations or growing ARR (if not revenue) faster than what seems possible.

This is not new, and my way to think about it (which I might have told some people from time to time) is:

“You see your own startup in the mirror, and all other startups through their press releases (or LinkedIn posts). Compare the difference between what you see in your mirror and what you write in your own press releases, and assume everyone else is doing the same.”

Therefore it is safe to assume that there’s a difference between the public picture a successful startup paints, and what is going on inside of it. Some real problems are likely left out what’s being highlighted, regardless how well it is supposedly going. So regardless of other people’s headlines, the best thing to do is usually to keep on building, selling and recruiting.

Legora raises $150m Series C, Stockholm’s latest unicorn

AI legal tech company Legora has raised $150 million at a $1.8 billion valuation Series C. The round was led by Bessemer Venture Partners.

Legora has 400+ law firms and in-house legal teams as customers across in markets.

Legora has offices in Stockholm, London, New York, Denver and Sydney and employes almost 200 people. The plan is to double in size (to almost 400 people, I’d assume) and establish more offices around the world.

Extremely impressive development since I saw CEO and co-founder Max Junestrand present the company at SSE Ventures demo day in August 2023.

Strawberry and ChatGPT Atlas

Web browsers with AI automation, like the Swedish-developed Strawberry and ChatGPT Atlas, are really starting to show how a new type of interaction with the web and web-based product can (and likely will) work. It is fascinating to explore and learn what can be done when the browser can run agents that do things for the end-user.

It is also interesting to think about how that is likely to change a bunch of things which could have significant economic/productivity impact.