😎 Watch Out for Founder-CEOs

What Happens When Losing is Personal — Plus, Ty Haney is Back at Outdoor Voices and Elon Gets His Shares

Author

Katie Perry
August 05, 2025

Welcome to Tuesday Thursday Saturday! Here, I share a snapshot of trending stories across business, tech, and culture three times a week, plus some updates from the daily financial news show I host. - KP

The Big Story: The Undeniable Danger of the Founder-CEO

Alex Karp is raising his voice. Again.

It’s ten minutes into Palantir’s Q2 2025 earnings call, and the company’s enigmatic Founder-CEO is getting excited. CEO commentary during these moments is designed to clearly articulate progress, a vision, and confidence in leadership. Most leaders favor gravitas over showmanship. But this comes more easily to some than others.

Karp has emerged as a cult icon among Palantir’s enthusiastic retail shareholder base. He’s emphatic, provocative, and idiosyncratic. He’s an unabashed techno-nationalist and friend and co-investor of Peter Thiel, yet he’s also described himself as a socialist.

He doesn’t fit nicely within any box. He once accused Palantir short-sellers of being high on cocaine. His hair defies gravity.

Image credit: LA Times

In many ways, Karp is the perfect embodiment of a modern founder-CEO. He’s real, he’s raw, and he gives a lot of f--ks. And you might say, “Well, isn’t that his job as CEO … to care more than anyone?” Think about it, though. There are levels to this.

My Stocktwits Daily Rip Live co-host, Shay Boloor, Chief Market Strategist at Futurum Equities, recently pointed out that founder-CEOs are likely operating with a level of ego and personal pride that non-founders are not. 

For people like Karp — he founded Palantir in 2004 and didn’t take it public until 2020 — there is a sense that one’s entire identity is wrapped up in their role as the captain of their ship. Business failures, and triumphs, are not easily separated from the individual. 

At the end of the day, humans aspire to be liked and respected. It really is that simple. For founder-CEOs, this universal truth makes business violently personal.

There are plenty of examples of ultra-successful founder-CEOs in our midst today, and that’s with good reason. Experts cite a litany of factors as to why this may be the case. 

One main reason is due to their inherent emotional and financial alignment. This could be a result of economic “skin in the game” — having your entire net worth or legacy wrapped up into the thing you're building would certainly cause you to feel a certain type of way — but it’s also about identity. Founder-CEOs often become synonymous with their products and companies. A failed business marks the suicide of a legacy, pending an epic comeback or reinvention, which few will attain.

Another factor is that founder-CEOs often come with deep domain expertise. They, after all, are the original “spotters” and solvers of the problem. More often than not, they’ve operated in the industry in which they are building. If they are a technical founder, they probably even wrote the first few lines of code.

Founder-CEOs often come with cultural advantages, too. With the inventor comes an aura of mystique, an army of proteges, and an organization that naturally adapts to the habits and ethos of its creator. Related, this can give founder-CEOs more leeway to push teams harder, or make bold, risky moves, because they go into these situations with the full support and backing of their people.

Not shockingly, data shows that founder-CEOs historically invest more aggressively in long‑term growth, spending up to 22% more on R&D and 38% more on capital expenditures than non-founder CEOs. 

Yet, in the same way that confidence can snowball into hubris, the distinct advantages of founder-CEOs can turn into setbacks as companies scale. Overconfidence bias, or making overly optimistic forecasts or acquisitions that fail to deliver returns, is definitely a thing among some founder-CEOs.

There’s also the concept of blind spots. Founder-CEOs, dogged in their vision for the future and perhaps colored by their experiences in the past, can be resistant to delegation or outside expertise. Some experts have referred to this as “founderitis.” 

Moreover, as a company advances to new territories in its maturation cycle, the skills of a management team must adapt in kind. For founder-CEOs without operational experience, this is where things like organizational structure and governance could be discounted. This is why smart founder-CEOs make strategic hires around them, filling gaps in the management ranks with people who have simply “been there before.” I’ve also heard this described as “hiring grown-ups.”

So, which is more “dangerous” — a maniacal founder-CEO, OR a veteran “ringer” with limited emotional baggage? Depends on how you perceive the word dangerous. Is danger a competitive advantage, or is it a risk to the long-term viability of the business, or is it a little bit of both?

This seems to be the case for Outdoor Voices, the cult athleisure brand founded by Parsons grad Ty Haney in 2013. The young founder-CEO built up her brand before it was taken over by retail veterans, who drove the business into the ground. But as of last month, she’s back at the helm. And of course, she announced this via some clever social media posts.

The stage of the company and specific dynamics of each founder must certainly be factored into this assessment. But if you want to look at the numbers, a Cambridge University study from 2009 found that founder-led CEOs outperformed the benchmark by more than 8% per year (this for the years 1993-2002).

It’s worth noting that this research is now more than 15 years behind us. A lot has changed since then, and you could argue that the changes we’ve seen in the public markets have only created tailwinds for founder-CEOs. Back then, social media was nascent, Robinhood was four years away from being founded, and “retail investors” were semi-professional stock pickers who doled out $10 or $20 bucks per trade (and this was considered the “discount” era).

Charisma has always been an important trait for CEOs, but these days, charisma can take many forms. It could mean you’re articulate, inspiring, and visionary. It could also mean that you take shots at short-sellers during CNBC hits so that your legion of everyday investors can turn you into a momentary Internet meme. 

It’s the attention economy after all, and perhaps more important than charisma is personality. Founder-CEOs, armed with the emotional trauma of birthing a company, seem to understand that authenticity, in addition to results, might just be the thing that hooks investors in for the long term.

In Karp’s closing remarks, he tells listeners that he’s been cautioned to tone it down (paraphrased) despite the “bombastic” results. A few minutes later, he added, “We’re sorry our haters are disappointed!”

What a world.

Daily Rip Live Recap: Musk Gets His Bag, BLS Data Drama, and How to Pick a Winner Among Losers

Every weekday, my co-host Shay Boloor and I cover the biggest market news and events LIVE on Stocktwits’ morning show, The Daily Rip Live. Yesterday, we welcomed Bloomberg’s Steve Hou to the show. In addition to being Bloomberg’s go-to quants guy, he also casually mentioned that he has a PhD in Economics. Not surprisingly, it was a legendary conversation, and we hope to have him back soon!

Here’s what we covered on Monday’s show:

⇢ 2:05 Chamath Palihapitiya takes a shot at Steve, and a Twitter tagline is born.

⇢ 5:40 Elon Musk gets his $29 billion stock package, no thanks to a shareholder vote. “All [he] has to do is stay!” - Taylor Swift $TSLA ( ▼ 1.79% )  

⇢ 10:45 Founder-mode CEOs and how ego factors into the equation, according to Shay (inspo for the post above!)

⇢ 16:50 Jobs data drama unfolds following last week’s big revisions. How often do we blame the statistician? (Not often!) Plus, are robots carrying the economy?

⇢ 24:11 September rate cut odds are now on the rise. What moves did the Fed make before, during, and around the dot-com bubble era?

⇢ 29:15 Pricey Palantir reports earnings $PLTR ( ▼ 9.07% )  

⇢ 33:45 Steve clues us in to his 'earnings inflection strategy' (w/ charts!) Look out for the “losers” who are consistently losing by less.

⇢ 52:20 What's up with Apple? Is it too little too late? Tim Cook hints at potential M&A appetite during last week’s earnings call, but this runs counter to their build vs. buy ethos. $AAPL ( ▼ 0.22% )  

⇢ 59:25 Steve’s Tariff factor index — did the trends begin before Liberation Day?

We’re live every weekday, Monday-Thursday, at 9 AM ET. Tune in!

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Robots are carrying the economy, according to my friend and overall brilliant human being Callie Cox, Chief Market Strategist at Ritholtz Wealth Management.

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Tuesday Thursday Saturday is written by Katie Perry, owner of Ursa Major Media, which provides fractional marketing services and strategy in software, tech, consumer products, professional services, and other industries. She is also the co-host of Stocktwits’ Daily Rip Live show.

Disclaimer: The contents here reflect recaps and summaries of pre-reported or published data, news, and trends. I have cited sources and context for the information provided to the best of my ability. The purpose of the newsletter is to inform and educate on larger trends shaping business and culture — this is NOT investment advice. As an investor, you should always do your own research before making any decisions about your money or your portfolio.