Mar 21, 2025 · 1h 11m · 20vc
Elias Torres, Co-Founder and CEO @ Agency: What No One Tells You About Selling Your Company · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, host Harry Stebbings interviews serial entrepreneur Elias Torres, who candidly discusses the psychological toll of selling Drift for 1.2 billion dollars, his highly aggressive philosophies on recruiting and building grit, and his vision for the future of AI and agentic software with his new venture, Agency.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 23.8% of the talking time here. How this is scored →
Harry as informed peer 3.8 Guest teaching 3.5 Guest disagreement 2.9 Harry pushing back 2.9
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 12:07 Rejecting incumbent AI execution
Elias forcefully shuts down Harry's suggestion that large incumbents are moving fast on AI, bluntly stating that Google 'fucked it up' and dismissing corporate PR as 'bollocks'.
Hardest push from Harry ▶ 14:09 Defending Google's distribution dominanceHarry refuses Elias's dismissal of Google, arguing directly that distribution and consumer touchpoints outweigh raw development speed in long-term platform wars.
Biggest teaching moment ▶ 29:32 Explaining how soft management ruined DriftElias educates Harry on why catering to employee feedback, executive coaches, and management 'carrots' directly ruined Drift's execution trajectory instead of building an enduring public company.
Harry holds his own ▶ 1:05:27 Arguing AI services outgrow tech providersHarry displays high market knowledge by citing his debate with Paul Graham regarding AI services revenue outstripping underlying software providers due to deployment complexity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Elias Torres on Drift and the Ego of Letting Go | 3 | 2 | 1 | 1 | Harry introduces Elias by quoting a philosophical tweet about pretending to be a nihilist and links it to a Jordan Peterson quote. Elias warmly explains the paradox of caring deeply while developing thick skin through entrepreneurial rejection. | |
| How Wealth Changes What You Care About | 4 | 4 | 3 | 4 | Harry challenges the conventional founder advice to 'tell your 21-year-old self it will be okay', arguing that fear drives success. Elias reframes this by insisting complacency brings happiness and explaining how his background in Nicaragua shaped his sense of relative difficulty. | |
| Escaping Revolution: Elias's Immigrant Story | 2 | 2 | 1 | 1 | Harry asks about Elias's childhood in Nicaragua following advice from Pat Grady. Elias shares a personal story about escaping revolution, facing homelessness, getting a green card, and discovering an IBM PC in L.A. | |
| Privilege, Grit, and Raising Children | 3 | 3 | 2 | 2 | Harry asks whether wealthy founders hold unfair advantages over those coming from poverty. Elias notes that grit exists everywhere and humorously recounts his daughter calling out his LinkedIn advice. | |
| The AI Debate: Speed, Distribution, and Agentic Software | 7 | 4 | 6 | 7 | Harry directly challenges Elias's belief that incumbent 'elephants can't dance', citing Adobe, Google, and Microsoft. Elias forcefully disagrees, arguing Google fucked up and Copilot isn't used, while Harry pushes back item by item on distribution advantages. | |
| Why Humans Block Innovation and the 'Bullshit' of One-on-Ones | 4 | 4 | 4 | 4 | Harry asks why large companies slow down and brings up management culture. Elias dismisses one-on-one meetings as bullshit, prompting Harry to challenge how his anti-meeting philosophy scales past 50 employees. | |
| The Shift to Small, High-Revenue Companies | 3 | 3 | 2 | 2 | Harry probes how smaller teams with high revenue will reshape organizational structures. Elias shares how customer support team sizes can be reduced via compute, despite middle-management enterprise resistance. | |
| How AI and Smaller Teams Impact Venture Capital and Equity | 5 | 4 | 5 | 3 | As a venture capitalist, Harry asks if smaller teams alter debt vs equity needs in venture capital. Elias agrees and calls bullshit on founders who plan to hire 1,000 sales reps in the age of AI. | |
| High Agency and Intensity: Elias's Hiring Strategy | 4 | 4 | 3 | 3 | Harry cites mutual friends praising Elias as a master recruiter and asks for his criteria. Elias describes his intense, in-your-face interview style, and Harry pushes on whether this style excludes talented introverts. | |
| Why Drift Failed to Go Public: Carrots, Sticks, and Inefficiency | 4 | 5 | 5 | 4 | Harry asks if leaders should adapt their management style to different personalities. Elias rejects adapting, labels Drift the biggest failure of his life for relying on management soft carrots, and explains why it didn't go public. | |
| Selling Drift and Achieving "Fuck You" Money | 3 | 2 | 2 | 3 | Harry bluntly asks how much cash Elias walked away with after selling Drift for $1.2 billion. Elias humorous deflects specific numbers while confirming it achieved life-changing money. | |
| Shifting to "Hire Slow, Fire Fast" | 3 | 4 | 2 | 2 | Elias notes Harry is straying from pre-agreed questions before detailing his updated 'hire slow, fire fast' strategy. He describes hiring five Northeastern students in one day and having them code at his home. | |
| Overcoming Ego in Hiring and the Truth About References | 4 | 4 | 3 | 4 | Harry asks how quickly a founder can fire someone without looking unfair. He plays devil's advocate for quota-deprived SaaS founders, but Elias firmly warns against making desperate hiring compromises. | |
| Job Hopping and the Pitfalls of Corporate Titles | 4 | 4 | 3 | 3 | Harry brings up job hopping and corporate title inflation. Elias agrees that titles are ego-driven nonsense and contrasts ephemeral growth hype like Cursor with durable B2B customer relationships. | |
| Ego, Relevance, and Post-Sale Depression | 3 | 4 | 2 | 2 | Harry asks about the emotional reality of selling a company. Elias candidly describes the post-sale depression of feeling irrelevant and becoming a 'nobody' after walking away. | |
| Sacrifices of the Entrepreneurial Father | 5 | 4 | 4 | 4 | Harry puts forward his personal view that elite founders are like selfish athletes who perform worse when family obligations dilute focus. Elias rejects this framing, proving he raised hundreds of millions while raising three kids. | |
| Marriage and Sustaining Relationships | 2 | 3 | 2 | 2 | Harry asks for advice on sustaining a 27-year marriage. Elias jokes that 'she's always right' and emphasizes balancing ego with serving others. | |
| Overcoming the Fear of Letting Down Your Family | 3 | 4 | 2 | 1 | Harry vulnerably admits feeling like a constant failure who lets people down across his various roles. Elias offers empathetic advice on releasing perfectionism and accepting doing one's best. | |
| Operating Mindset and the Choice to Build | 5 | 3 | 2 | 2 | Harry asks about transition from operator to investor and mentions his viral tweet arguing AI services will outgrow AI technology companies. Elias agrees, noting human hand-holding is the bottleneck in AI adoption. | |
| Timeline of AI Adoption and Economic Impact | 4 | 3 | 3 | 3 | Harry leads a quick-fire round on AI adoption timelines, AGI GDP projections, skin care routines, and market bets. Elias predicts a slow adoption timeline and names Salesforce as his biggest stock short. |
Statements from this episode (39)
Elias Torres calls selling Drift the biggest failure of his life
“Drift is the biggest failure in my life.”
Torres claims Drift would be public without executive equity concessions
“I would have a public company right now if I, if it wasn't for like all those carrots that I gave and candy bars and trophies.”
Torres: Wealth Eliminates One-Third of Everyday Stresses
“So that is a huge release, you know, of stress that I just don't care about that stuff anymore. So that just takes like, I don't know, one third of the problems, and I'm just like, ok, I don't care, just pay it, you know, move on.”
Elias Torres: Code to build an LLM fits on one page
“The code fits on a, like, a page on the screen.”
Elias Torres got his start in tech using a stolen IBM computer
“He bought, like, a stolen computer. Like, people came and sold him, you know, and so I, he put it in the garage, and he said, go play with it. And so that's, it's like an IBM computer, like, you know, in the eighties, and I would be typing my homework in this …”
Elias Torres manufactures adversity to raise gritty kids in wealth
“I just try to manufacture adversity. That's all I can for them.”
Torres: 400,000-person corporations cannot move fast despite Lou Gerstner's claims
“What I learned was that a four-hundred-thousand-person company just can't move as fast. Lou Gerstner was the CEO at the time and wrote a book called, like, Why Elephants Can Dance, right? And I don't think, I disagree with him. Elephants can't dance.”
Torres: Google AI products don't work and Notebook LM is already dead
“They invented this Transformers paper, and everything they put out doesn't work. Like Notebook LM, the great one, like it's already dead, right? The project. So it's like they're trying so hard, but they can't do it.”
Torres: Nobody is using Microsoft Copilot because the product doesn't work
“Copilot, everybody was like, they're just ahead making all the money first because people, the problem is people are, they just have so much hard time trusting someone, right? And so they're reaping the benefit of being early, But nobody's using the product, r…”
Torres: Future software will eliminate human operators, functioning like driverless cars
“Software that has been built in the past 2030 years had the assumption, it was built kind of like we build cars. We build a car all around, and we build the entire environment, so a human goes and drives the car. Right? It requires an operator. The future is n…”
Torres: Agency operates its 15-person team on a single daily meeting
“Right now at agency, I have no meetings with anybody, right? We're like 15 people. We have one meeting for the whole company, for the whole team. Show me what you did yesterday, show me what you're gonna do today. That's all we do in that meeting.”
Torres: Drift scaled to 800 total employees, including 200 in customer support
“I had 800 people, I had 200 in CS.”
Torres: CEOs err by delegating AI software implementation to middle management
“CEOs are making a big mistake right now. They're like, I talk to them and they're like, yes, this is what I want. I'm down. Elias, let's get agency in here right now. And then they pass me down to the next person and to the next person.”
Elias Torres: AI Startups Are Trading Human Headcount for Compute
“We'll have smaller teams, but we still need more compute. I mean, we're just really trading people for compute.”
Elias Torres: AI Startups Will Suffer Far Less Equity Dilution
“A lot less equity will be spent on, on, on the team, right? Because you're not gonna need rounds and rounds and Distributing equity after every round to hundreds and hundreds of people.”
Torres: AI will displace B2B corporate workforces despite optimistic predictions
“That's bullshit, right? I just, it's just, you have had some guests here that I love and respect, but they're like, Oh yeah, we're gonna get larger, you know, in five years, and I'm like, what? I just saw something, you know, somebody posted on Twitter, it's l…”
Elias Torres avoids hiring introverted software engineers
“And so I don't, I tend to not hire like that many introvert engineers, right?”
Elias Torres tests engineering candidates by reviewing live Git repos
“Show me, open up your computer. I want to see your Git right now. Show me what you committed. Show me your code. Let's discuss that. Did you really build that? Who was it? So I'm just like, I don't care about my questions. I just go bang, bang, bang, bang. I w…”
Torres: Incumbent tech firms must cut headcount by 80% to survive
“If they do what Twitter did, if they reduce themselves to 20%, and build an amazing product, and are willing to break all their pricing models and revenues and change all of that, then they will survive.”
Elias Torres: Founders waste time being frugal instead of focusing on customers
“I think people are wasting their time trying to be all frugal or this. I want to focus my time on the customers, right? And my team and my people.”
Torres built all his previous startup teams with Northeastern University students
“Before all my companies, I've built them on the backs of Northeastern students. They're amazing people. They're the best.”
Torres: Founders spot bad hires within two weeks but ignore signals
“In reality, most people should know, like, within the first week or two, it's just, they just reject those signals.”
Torres: Overrode interview panels to make hiring decisions at Drift, HubSpot
“By the way that I ran interview at HubSpot and Adrift, everybody, I would help, I have a panel of people interviewing, But I would always interview myself. I will do the informal, I will do the formal, I bring them in, and then I do the closing. But I let them…”
Torres: Long tenure at a single company can be a hiring red flag
“If you stayed there for a long time, it's a red flag too.”
Torres: Cursor's Fast Revenue Growth Is Fragile Due to Low Switching Costs
“The cursors and all that stuff, like you can easily switch to like windsurf and you can switch to this and you can go back to copilot and like, so that revenue could disappear. This is a brand new phenomenon and we do not know how it plays out.”
Torres: Having children at a younger age is optimal
“The best time to our children is when we're younger, unless we have unlimited resources, right?”
Stebbings: Having a Family Prevents Founders From Operating at Peak Performance
“When you have the kids and the wife, suddenly, you are no longer the most important thing. That sleep schedule goes to shit. And your ability to inspire in that meeting is completely off. Your ability in fundraising, it's all, you're not performing at peak.”
Torres: Raised Hundreds of Millions of Dollars While Raising Three Children
“Because I was able to do all that. I raised hundreds of millions of dollars going through all that stuff, right?”
Elias Torres Regrets Not Being Tougher When Raising His Children
“I wish I would have been tougher with them”
Torres was the first investor in Klaviyo
“That Klaviyo, you know, I'm a first investor, good friends with Andrew, right?”
Torres convinced Klaviyo founder Andrew Bialecki to take VC funding
“I convinced him to take VC money.”
Torres is holding his Klaviyo stock because it remains underappreciated
“A thousand percent, so that's why I'm not selling my stock.”
Torres: Building a company is much easier and more fun than investing
“For myself, I'd rather build, man. It's so much easier, so much more fun.”
Elias Torres earned $2 million in six months consulting on AI
“The reality is that, you know, I made, like, two million dollars in, like, just over, like, six, seven months consulting AI.”
Torres: Humans are the primary blocker to AI adoption
“I think that humans are the biggest blocker to adoption, and they're gonna need a lot of hand-holding and help.”
Torres: AI adoption transition will take five to ten years
“I'm on the longer side. I think there's a lot of hype. This stuff, we're not we're not gonna, like, even in the industrial age and the revolutions, right, GDP was growing at one percent, two percent. I don't think we're gonna grow, like, at 10%, 20% in one yea…”