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Miles Dieffenbach
@Curiousjorge65
@CarnegieMellon Endowment Managing Director of Investments / Used to play football @ PSU & Steelers / Tech enthusiast / Tweets my own
Pittsburgh, PA
linkedin.com/in/miles-dieff…
Joined October 2012
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  • Pinned
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    Miles Dieffenbach
    @Curiousjorge65
    Aug 4, 2025
    What a fun @twentyminutevc episode with @HarryStebbings. Exciting to share about how we at CMU think about investing in VC & other asset classes. Thanks for having me on! open.spotify.com/episode/6OCq8W… 📷 youtu.be/NMuoR8hhupg?si…
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    Harry Stebbings
    @HarryStebbings
    Aug 4, 2025
    Let’s be honest. Most podcasts suck right now. Repeated guests. BS first principles “frameworks”. The best podcasts are with people with immense power who have never spoken publicly before. Today, we go behind the scenes into @CarnegieMellon’s $4BN Endowment Fund. - Why 90% of
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    Miles Dieffenbach
    @Curiousjorge65
    Aug 8, 2018
    It’s been quite the journey, but I am proud to say that I am in remission and presently have no cancer in my body! This wouldn’t have been possible without God, my friends and family, UPMC, and Carnegie Mellon University. Thank you all for the support! #burntheships
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    Miles Dieffenbach
    @Curiousjorge65
    Mar 30, 2018
    The battle begins! #burntheships
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    Miles Dieffenbach
    @Curiousjorge65
    Aug 27, 2025
    OAI at $500b and $GOOG at $2.5trn seems so crazy to me. Think about how long and amt of $ it would take OAI to build Cloud at $50b ARR, TPUs, Waymo 250k rides a week, YT >$50b in revs, leading LLM w Gemini, Deepmind, Search w $200b revs growing 12%. OAI has ChatGPT $13b ARR.
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    Miles Dieffenbach
    @Curiousjorge65
    Jul 2, 2025
    Index Ventures doesn’t get enough credit. Largest shareholder in Wiz, second largest in Scale AI, largest in Figma, all are generational >$15b exits within 4 months. Top 3 VC firm globally, and arguably #1 IMO due to the consistency in fund size and returns they put out
    153K
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    Miles Dieffenbach
    @Curiousjorge65
    Dec 23, 2024
    CoStar, the leading vertical SaaS company in Real Estate doing $2.7b in revenue this year, owns a plane that runs 7 days a week/52 weeks a year tracking construction projects throughout the U.S. Talk about proprietary vertical data integration! $CSGP
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    Miles Dieffenbach
    @Curiousjorge65
    Jun 18, 2025
    Wrong take. Ellison is much richer because he didn’t sell shares and has steadily been buying back 2% of the company every year for 30 years! Increase ownership from 17% to 40%. $CRM made a lot of dilutive acquisitions and Benioff steadily sells his shares yearly
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    sam lessin 🏴‍☠️
    @lessin
    Jun 18, 2025
    Oracle is 2x a Salesforce, but Ellison is worth 25x Benioff?…. What This Says about the limitations of the SaaS business model.
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    Miles Dieffenbach
    @Curiousjorge65
    Nov 7, 2022
    If HashiCorp, at $455 million of ARR growing 50% YOY, is valued at 6x ARR, what does that mean for the outcomes of the ~1,500 private unicorns globally? A lot of pain to be felt in late-stage VC.
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    Miles Dieffenbach
    @Curiousjorge65
    Sep 6, 2024
    Surprised more allocators don’t talk about how significantly VC has underperformed the Nasdaq over past 25 years. Top quartile net DPI over that time is 1.9x, rolling 10yr for Nasdaq is 3x. VC funds have only gotten bigger, more illiquid, with high fees, hard to see a reversal.
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    Miles Dieffenbach
    @Curiousjorge65
    Apr 19, 2018
    Huge thanks to @CoachLimegrover, @PennStateFball OLine and @McSorley_IX for the photo, you guys are awesome!! #WeAre
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    Miles Dieffenbach
    @Curiousjorge65
    May 2, 2015
    Proud to say I am now a Pittsburgh Steelers! @steelers
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    Miles Dieffenbach
    @Curiousjorge65
    Sep 8, 2014
    Thank you to all the former and current players who stood by us. Also want to thank our incredible fans! Now lets go and beat Rutgers #weare
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    Miles Dieffenbach
    @Curiousjorge65
    Nov 22, 2024
    Best S1 breakdown yet. Servicetitan isn’t going public because of the IPO window being “open”, but because they have a compounding ratchet from their last round. If they could’ve raised clean private capital, I bet they’d stay private! meritechcapital.com/blog/serviceti…
    168K
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    Miles Dieffenbach
    @Curiousjorge65
    Oct 1, 2016
    What a clutch play!! Way to fight til the end. Also Tyler Davis is a legend dude literally has never missed.