Josh Reeves
Co-Founder and CEO, Gusto. On 5 shows, 4 appearances, plus 1 compilation re-air not counted. The Shows tab opens the full record on each.
founderexecutiveinvestor@joshuareeves ↗LinkedIn ↗gusto.com ↗
Josh Reeves co-founded Gusto in 2011, serving as its chief executive officer. Previously, he earned degrees in electrical engineering from Stanford University and founded the startup Unwrap.
5shows
4appearances
52statements
16resolved
11supported
0contradicted
69%fully supported
7said about them ↓ Everything Josh Reeves said on any show that made the record, most notable first. Each card names its show and opens the statement there.
Reeves: Gusto rejected 11 VC firms to raise seed solely from angels
“We had, I think, like, over 11 VC firms offer to invest. We actually chose to do the round with no VC firms. It was all angels, so we raised from, you know, twenty-plus CEOs and founders. It was, you know, the CEOs and founders of, you know, PayPal and Stripe …”
Gusto will eventually go public, says CEO Josh Reeves
“At some point, Gusto, you know, will be a public company.”
Reeves: Compliance and mission-critical software cannot rely on standard beta launches
“And I think this is a principle that applies to a lot of companies, maybe all, I'm not sure. But especially when you're in a space that has compliance or really solving mission critical activities. For us, it's like getting people paid on time correctly, accur…”
Reeves: Silicon Valley 'land grab' mentality fails to build durable businesses
“I think especially in Silicon Valley, the term land grab can be used as a way to rationalize kind of throwing out every business practice and just doing whatever it takes to win. That doesn't actually lead in my opinion to really long-term durable businesses.”
Reeves: Over 98% of Gusto free-trial users convert to paying customers
“So we give folks a one or two month free trial when they start and over 98% convert from the free trial to being a paid customer.”
Reeves: Gusto rejected all VCs in seed round, raised from 20 CEOs
“And so our seed round, which we did in 2012, we actually had several different VC firms offer, and we actually declined all VC firms. We did a seed round with about 20 CEOs, and it was all individuals. And today, We've done that in every round. We have about 7…”
Reeves: Gusto serves over 400,000 businesses, led by word of mouth
“Even today in 20, 25 with, you know, over 400,000 companies on Gusto and us adding A lot every year. Organic, word of mouth, remains the biggest driver of leads in Tupper Funnel for us”
Reeves: Small businesses need opinionated software partners, not just passive tools
“Small business, you know, they want an opinionated partner, right? They don't want just a tool. They want just a set of menu of options. They're super busy. They're wearing many, many different hats, and they don't, frankly, have the resources to go hire all o…”
In 2011, 40% of US companies did payroll manually, risking massive fines
“When we started Gusto, you had close to 40% of companies in the U.S. Doing payroll by hand. You had close to that same percentage, you know, 30 to 40% getting fined, penalized by the government for making mistakes. You had billions and billions of dollars of p…”
Reeves views payroll as the ultimate non-optional employee system of record
“We chose payroll to start because it is the de facto system of record for employee data, and it's the least optional part of the stack. Another way to think of it is, like, if you don't pay someone, they quit, and so it is the medicine, not the vitamin”
Reeves: Organic growth must be the lifeblood for SMB software
“With smaller business, you're going to have a lower ACV. Like, organic has to be the lifeblood of your growth engine.”
Gusto will eventually serve companies of all sizes globally, says Reeves
“That means eventually Augusta will be serving all size companies in all countries around the world with, you know, all pain points tied to running a business.”
Reeves: Essential SMB software can build $100B+ companies
“Companies like Shopify, Square, Intuit have proven that you can build, like, hundred billion dollar plus companies if the numbers are working right, if you're medicine, not vitamin for a small business customer”
Reeves: Customers loving a product primarily for pricing is a warning flag
“I think it's a flag if people love a product because of pricing is number one, like pricing was number like six. And we had people telling us like, you should raise your prices, your two sheets, which is also a pretty good sign, frankly, but like the number on…”
Reeves: Scaling with poor unit economics turns small bad businesses big
“Before you scale it, you have to prove out the unit economics, because if you scale something with poor unit economics, it just means you're going to have a small bad business become a big bad business, right?”
Reeves: Treat fundraising like hiring permanent, part-time teammates
“When I say that fundraising is like hiring, what I mean is, if you can, try to apply the same logic I just shared about hiring a teammate to fundraising, right? This is someone that's going to join your company, Albeit part-time, not full-time. Although a lot …”
Reeves: Gusto serves over 25,000 paid small business customers across America
“We have now over 25,000 small businesses spread across the country over half a percent of all employers in America using the product, partnering with us.”
Reeves: About 40% of US companies were penalized yearly for manual payroll
“Like, about 40% of companies were doing it manually and getting fined every year because you have local, state, federal.”
Reeves: Gusto co-founder Eddie Kim lived in a closet for five months
“Eddie, Eddie slept and lived in that closet for about five months, and it fit a air mattress you know, like I said, it had a skylight and it was also where my other roommate stored all of her clothes, though, so it was kind of both a natural closet and a quasi…”
Reeves: Gusto initially ran payroll via in-person visits on a co-founder's laptop
“So the first set of companies that onboarded to Gusto, and we had a different name at the time than Payroll what that meant was we would go to your house and You would type into, it was typically Tomer one of my co-founders, and we love to say you can't spell …”
Reeves: Gusto's first cohort was restricted to salaried California first-time employers
“So there was a really clear scoping here to companies in California that had never used payroll before, were paying employees for the first time. They were all salaried employees.”
ZenPayroll added over 100 self-serve customers in its first month
“In that first month through end of January, we added over a hundred customers, and the hundred customers, the majority of which, set up, onboarded without talking to us, you know, they could do it on their own”
Reeves: 40% of US companies faced annual penalties for payroll mistakes
“40% of companies in the U.S. Were making mistakes and getting penalized every year.”
The other half of the tape: Josh Reeves's own voice is left out of every number here. Other people bring the name up 5 times in 3 episodes across the shows. 2 statements on the record name them. every mention, with the transcript →
Who brings them up most Nathan Latka 3Jason Lemkin 2
Statements about Josh Reeves, by other people (2)
Lemkin: Gusto CEO Barred New Executives From Working For 60 Days
“When Josh would hire a new executive, I think he wouldn't let him work for, 60 days.”
Every mention by year
tap a year for its mentions
Top Founders 3
the Official SaaStr Podcast 2
2024 2 mentions in 1 episode
2017 1 mention in 1 episode
One line per show, most statements first. The link opens Josh's full record on that show: the calibration, argument clarity, speaking style and every statement made there.
| Show | Role there | Eps | Statements | Record | |
|---|---|---|---|---|---|
 PRODUCT MARKET FITLEDGER | Co-Founder and CEO, Gusto | 1 | 20 | 63% 5/8 | full record on A Product Market Fit Show → |
 Y COMBINATORLEDGER | Co-Founder and CEO, Gusto | 1 | 11 | 83% 5/6 | full record on the Y Combinator Startup Podcast → |
| TOP FOUNDERSLEDGER | Co-Founder and CEO, Gusto | 1 | 8 | 100% 1/1 | full record on Top Founders → |
| SAASTRLEDGER | Co-Founder and CEO, Gusto | 1 | 7 | 0% 0/1 | full record on the Official SaaStr Podcast → |
 FOUNDER'S JOURNALLEDGER | Co-Founder and CEO, Gusto | 0 +1 | 6 | — | full record on Founder's Journal → |