Apr 1, 2022 · 37m · 20vc
20VC: The Biggest Mistakes Startups Make Hiring, The 2 Reasons Startups Fail and How to Avoid Them, Why Most Startup Equity Plans are F****** and Why You Should Scrap Titles From Your Company with Eddie Vivas, Founder & CEO @ Curated
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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 Eddie Vivas, founder and CEO of Curated, to discuss startup execution, sustainable hiring, and long-term capital allocation. Vivas shares key insights from building Curated, emphasizing missionary culture, custom technology infrastructure, and patient venture growth over premature scaling.
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 33.1% of the talking time here. How this is scored →
Harry as informed peer 4.0 Guest teaching 3.7 Guest disagreement 2.7 Harry pushing back 4.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 22:03 Eddie calls fast hiring logic 'stupid'
Eddie forcefully rejects the premise that founders should hire quickly to satisfy investors or extend runway, calling the bums-in-seats mentality stupid.
Hardest push from Harry ▶ 22:03 Harry challenges Eddie's go-slow hiring adviceHarry directly counters Eddie's philosophy by presenting pushback from real founders facing shrinking runways and demanding investor benchmarks.
Biggest teaching moment ▶ 22:49 Eddie breaks down vanity metrics versus true business valueEddie educates the host on how founders burn capital to hit short-term ARR metrics without actually improving underlying unit economics or business sustainability.
Harry holds his own ▶ 23:16 Harry cites VC market realities driving rapid ARR scalingHarry uses his perspective as an active investor to point out that venture capital markets actively celebrate and fund startups scaling from zero to $3M ARR in six months.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Eddie Vivas's Unconventional Path into Tech | 2 | 1 | 1 | 3 | Harry prompts Eddie to share his background after dropping out of high school and packing boxes. Harry interrupts twice to probe deeper into Eddie's personal conviction and mindset during tough times. | |
| The Founding Story and Aha Moment Behind Curated | 2 | 3 | 1 | 2 | Eddie recounts the origin story of Curated, illustrating his point with a story about buying improper ski gear. Harry mostly guides the narrative with standard open questions. | |
| Lessons from Past Ventures and Long-Term Mindset | 4 | 4 | 4 | 5 | Harry brings up a counterpoint from founder Joe Fernandez that serial entrepreneurship is overrated, prompting Eddie to directly disagree. Harry also interrupts twice to force Eddie to clarify what specific foundational elements matter most. | |
| Compound Startups and Build vs. Buy Decisions | 5 | 4 | 2 | 4 | Harry invokes Parker Conrad's compound startup concept to question Eddie on why Curated built so much custom technology instead of buying off-the-shelf software. Eddie explains why stacking 90% solution SaaS tools creates a mediocre experience. | |
| Validating Product-Market Fit Through Metrics and Intuition | 4 | 4 | 2 | 4 | Harry pushes Eddie to identify how an analytical founder like himself could ruin product-market fit. Eddie details the operational metrics, like 1-2% return rates and 50% expert tip rates, that proved product viability. | |
| Hiring Missionaries, Equity Ownership, and Compensation Plans | 4 | 4 | 2 | 4 | Harry challenges Eddie on how to practically distinguish true missionaries from smooth interviewers, and asks for specific equity structuring advice. Eddie advocates for generous equity plans and lower cash salaries. | |
| Organizational Transparency and Common Hiring Pitfalls | 6 | 5 | 6 | 6 | Harry pushes back on Eddie's advice to hire slowly by bringing up founder feedback about runway pressure, and cites VC behavior that rewards quick ARR scaling. Eddie dismisses the fast-hiring logic as stupid and rejects blaming VCs for bad founder decisions. | |
| Founder Secondaries and Evolving Relationships with Wealth | 4 | 4 | 3 | 4 | Harry raises concerns about early-stage founders taking millions off the table via secondaries. Eddie agrees that massive early founder secondaries send bad signals while defending secondary liquidity for long-tenured employees. | |
| Leadership Weaknesses, Scrapping Titles, and Cultivating Debate | 5 | 4 | 3 | 5 | Harry challenges Eddie's strict data-backed ideation policy, asking whether requiring data up front stifles raw creative ideas. Eddie clarifies how operating priorities balance structured debate with open ideation. | |
| Fundraising Common Mistakes and Investor Selection | 4 | 4 | 3 | 3 | Eddie criticizes competitive fundraising auction processes and over-indexing on high valuations. Harry then transitions into a quickfire round covering leadership, weaknesses, and future vision. |
Statements from this episode (20)
Vivas Grew Early Recipe Website to $20,000 Monthly in Six Months
“I built a recipe cookbook website. And I went from making like, I don't know, 1800 dollars a month to like 20,000 dollars a month in a matter of six months.”
Vivas: AppLovin Was Spun Out From My First Ad Tech Business
“So we sold that company. But before we did, we spun out a few assets. One of them was called Bright, which I went to go focus on. And then another one was called Applovin, where my brother and my co-founder Adam Fergie went to go focus on.”
Vivas: Pushing Extreme Office Hours Burns Out Top Startup Talent
“And the people who stick around will end up just being the people who aren't your stars in the first place. Cause your stars want to be learning and they want to be happy and they want to be creating impact.”
Vivas Actively Seeks Out Failed Founders When Angel Investing
“When I invest, I very much look at failed entrepreneurs. I think it's incredibly humbling.”
Vivas: Serial Founders Get Investor Leeway for Long-Term Execution
“That difference between being able to be long-term focused versus short-term focus is a huge, huge, huge advantage. I always tell Entrepreneurs, like, don't take this advice from me, because what I do as a repeat entrepreneur is different than what you're goin…”
Vivas: Curated Accepts Only 1% of Expert Applicants
“We'll receive a hundred applications, and we've learned we can only really accept one.”
Vivas: Curated Connects 95% of Users to Experts Under One Minute
“95% of the time, we're connecting you with somebody in under a minute.”
Vivas: Stacking 90% Software Solutions Creates Mediocre Technology
“One of the things we've come to terms with is if I stack a bunch of 90% solutions on top of each other, it gets really mediocre really quickly.”
Vivas: Curated Maintains a Product Return Rate Between 1% and 2%
“Our return rate is between one and two percent, meaning people shipping the items back.”
Vivas: Consumers Cover Half of Curated Expert Compensation Via Tips
“Half of expert compensation is actually covered by the consumer via tips.”
Vivas: A FAANG VP Role Is the Most Sustainable Wealth Builder
“VP at a FANG is the most sustainable way to make a considerable amount of wealth.”
Vivas: Curated Lost Only One Employee Out of 135 Last Year
“I think we've lost one person in the last 12 months, right? And we're a 135 people. I think over the course of the history of the company, we've lost less than I can count on my hand.”
Vivas: Smart Employees Will Figure Out Company Reality Regardless of Secrecy
“If you hired smart people, they're going to figure the shit out anyways. You can hide things from dumb people. Smart people are going to figure it out, so you might as well be straight up. I mean, because if I have a sense of urgency behind certain decisions, …”
Vivas: Convincing Candidates by Selling Dreams Is a Major Hiring Mistake
“The biggest mistake I've made in hiring is trying to convince people to join us. And I think it's that if I sell the dream and I convince you to come and inevitably the dream doesn't come true, you're going to be demoralized. You weren't really that bought in …”
Vivas: Excess Venture Capital Is Funding Lower-Quality Founders
“Right now there is a lack of high quality entrepreneurs and there's an excess of capital. And so people, investors are trying to fund whatever they can.”
Vivas: Curated Employee Secondary Liquidity Take Rate Is Under 10%
“We've offered our team a few secondaries, and the take rate has been less than 10%. In one case, we didn't even have enough secondary demand to fill, to cover the legal fees.”
Vivas: Founders Taking $10M in Early Secondaries Send Weird Signals
“Early companies found are taking ten million dollars off the table. Personally, I think it sends a lot of weird signals.”
Vivas: Curated Has Scrapped Employee Job Titles Entirely
“For starters, one of the things we do is we don't have titles of the company.”
Vivas: LinkedIn's Job Hierarchy Stifled Junior Employees' Correct Ideas
“One thing I observed when I worked at LinkedIn was if a director said something and an associate was in the room, the director was always right, But the associate often was the one who was right, but just because the more senior person was the one who said som…”
Vivas: Early-Stage 'Dumb Money' Gives Founders Rope to Hang Themselves
“And I think, especially in the early stages of a business, dumb money is just giving you a longer rope to hang yourself with versus Smart money and really strong investors will really call you out on your bullshit, push you on.”