Small Business

topic on 18 shows · 38 statements across 36 episodes

the Y Combinator Startup Podcast Founder's Journal Mixergy More or Less We Live to Build American Optimist the Knowledge Project BigDeal the Official SaaStr Podcast Starter Story the Startup Ideas Podcast Top Founders How I Built This the a16z Podcast TBPN 20VC A Product Market Fit Show Capital Allocators

38 statements about Small Business, every show

a16z Insight
Rampell: Small businesses are defended by the accumulation of required labor
“But one of the things that makes a small business somewhat defensible is actually it is an accumulation of people that are required to deliver the end product.”
Alex Rampell Jul 29, 2026 ▶ 42:43 “Every small business should run itself” | Lassie with a16z
Y COMBINATOR Prediction Not checkable as stated
Chou: Massive Companies Will No Longer Dominate in the Future
“And I actually think there's going to be way more small business in the future. You're not going to have like massive companies anymore that are dominating.”
Bryant Chou Jun 19, 2026 ▶ 21:44 The Age Of The 40-Year-Old Solo Founder Is Here · Y Combinator
BIGDEAL Opinion
Sanchez: No stock is as reliable as a business with weekly cash flow
“I don't think there's another stock as reliable as a business that pays you every week.”
Codie Sanchez Apr 14, 2026 ▶ 12:52 How to Make the Greatest Comeback of Your Life.
AMERICAN OPTIMIST Assertion Contradicted
Fry: Gallup ranks small business as America's most trusted institution
“Gallup runs a poll every year on the top institutions that Americans trust. Small business has been number one since the poll started. It is 44% higher than Congress, obviously. It's also 22% higher than the healthcare system and it is remain number one.”
Will Fry Apr 9, 2026 ▶ 11:09 How to Turn $15K Into $1M in 2026 · Joe Lonsdale
Sadan: Duda Has Not Spent One Dollar Acquiring SMBs Since Agency Pivot
“From that day onwards, we didn't spend a dollar until today to acquire a small business.”
Itai Sadan Jan 6, 2026 ▶ 24:16 65% of Their Sites Now Start This Way (Most Founders Miss It)
MIXERGY Insight
Foster: AI Enables Small Businesses to Automate Previously Cost-Prohibitive Tasks
“AI allows you to put brains in your business in places that was really hard to put brains in the past. It was very manual, very expensive, and mostly, especially for small business, you're just like, I'm just not going to do it.”
Wade Foster Dec 19, 2025 ▶ 5:50 #2289 Building companies using Zapier’s AI automations
WE LIVE TO BUILD Prediction Not checkable as stated
Weldon: Small businesses will get left behind in AI agent adoption
“My experience with small business, they're going to get left behind in a lot of this. The SME and UP are really going to take advantage of this.”
Jim Weldon Jul 25, 2025 ▶ 9:09 He Named His Agents and Gave One a Team of Five
BIGDEAL Insight
Sanchez: Being the first to respond wins small business customers
“Because what's the number one reason why somebody hires one small business over another? You're the first to respond.”
Codie Sanchez Jun 23, 2025 ▶ 27:42 How I Built 12 Income Streams Without Tons of Cash
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…”
Josh Reeves Mar 18, 2025 ▶ 22:55 From A Pivot To Building A $9.6 Billion Payroll Company · Y Combinator
BIGDEAL Assertion Partly supported
Sanchez: 60% of all millionaires own a small business
“Well, we know that 60% of all millionaires own a small business.”
Codie Sanchez Feb 20, 2025 ▶ 12:08 They’re Lying to You About Getting Rich
Leventhal: Restaurants are orders of magnitude harder than other small businesses
“If you think about the moving parts at the average independent restaurant and how complicated The production and assembly and delivery of food is to the table, and you compare that to any other small business, it's orders of magnitude more difficult.”
Ben Leventhal Jan 20, 2025 ▶ 25:20 Resy and Eater: Ben Leventhal
KNOWLEDGE PROJECT Assertion Not checkable as stated
A small business needs 20 positive reviews to counteract one negative review
“The average small business needs 20 positive reviews to overshadow one negative review.”
Codie Sanchez Jan 7, 2025 ▶ 1:47:41 Codie Sanchez: Your Blueprint to Financial Freedom
TBPN Insight
Hays: SMB buyers face adverse selection against private equity competitors
“This whole X movement around you should buy a small business because there are thousands of private equity bros that are highly trained, highly efficient, ruthless, that are all hunting for these same deals. And one, given their experience, they can probably p…”
Jordi Hays Dec 2, 2024 ▶ 2:05:21 How BILLIONAIRES dress for XMAS (ep17)
SAASTR Insight
Lang: SMBs only use five or six universal multi-product add-ons
“You want to go after Products that have potentially a hundred percent time, right? Where it's a hundred percent of your install base. And it turns out there's not that many of these, right? Cause like, you know, if you go down the stack of like what a small bu…”
Daniel Laniado (Daniel Lang) Sep 6, 2024 ▶ 9:06 Why Vertical SaaS is Booming, And How to Get 110% NRR from SMBs, with Jason Lemkin + Mangomint's CEO
BIGDEAL Assertion Partly supported
Average US small businesses sell for $800K versus $198K for restaurants
“The average small business in the U.S. Sells for around 800,000 dollars. The average restaurant goes for a 198,000 dollars.”
Codie Sanchez Aug 7, 2024 ▶ 1:19:45 How to Build a $10M+ Online Empire (feat. Joshua Weissman)
SAASTR Insight
Chestnut: Infusing humor and personality into the app was Mailchimp's key early unlock
“Turned out small business customers running a small business is dismal. I've learned over the years and they really need like A ray of sunshine, some sense of hope some kind of humor in the app, and so I think that was sort of the, that was the thing that kind…”
Ben Chestnut Jun 11, 2024 ▶ 11:07 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
SMBs Struggle to Calculate Data ROI Compared to Enterprise Customers
“In selling to the enterprise. As an example, it's easier for there to be a calculation of impact. Like how is this data actually guiding decisions? How are we able to make real value out of it? And then you can attach a fee to it. A small business. And I thoug…”
Dane Atkinson May 27, 2024 ▶ 8:57 Ex-Squarespace CEO on how to sell to SMBs, build tight feedback loops, & stay close to customers ... · PMF Show
Selling to SMBs Requires Transformative Value, Not Minor Iterative Savings
“Now the threshold is you have to be an epic salt, particularly in small business. You can't walk into small business and be like, I'm going to save you three percent on your business. I don't care. I don't have time. Wait, what the hell are you doing? Right? I…”
Dane Atkinson May 27, 2024 ▶ 26:05 Ex-Squarespace CEO on how to sell to SMBs, build tight feedback loops, & stay close to customers ... · PMF Show
Pitching Extrapolated Time Returns to Small Business Owners Is Unintelligible
“A small business doesn't know how to vector their time, you know, calculate all that in. If you come at them with an extrapolated return, it's unintelligible.”
Dane Atkinson May 27, 2024 ▶ 36:10 Ex-Squarespace CEO on how to sell to SMBs, build tight feedback loops, & stay close to customers ... · PMF Show
Rutledge: Small business owners routinely fail to delegate their domain craft
“I am a marketer by trade. I'm unwilling to give the marketing responsibilities to the marketing person that I hired and is now on salary. It's not an uncommon story in most small business.”
Tom Rutledge Apr 10, 2024 ▶ 7:36 Accounting Is Not a Numbers Game - Tom Rutledge on Why
MORE OR LESS Prediction Not checkable as stated
Dave Morin: AI-empowered small teams will challenge standard VC models
“There's all of these new tools that the AI revolution is putting out into the ether. That's that, Sam, I think you're very right. Are going to empower the small business. They're going to empower the small team of people to make a lot of cashflow to make reall…”
Dave Morin Nov 10, 2023 ▶ 49:31 #22: Your GPT Will Make More Money Than Your Substack? Please Tell Us More… · More or Less Podcast
Smale: Average small business sells for 4x to 10x annual profit
“Like the average small business is probably in the four to 10 times annual profit range.”
Thomas Smale Apr 17, 2023 ▶ 12:36 Zero to $1.1B from Flipping Websites
Huber: Operating real estate as a GP is a competitive small business
“If you're a GP like me and you're actually buying real estate and trying to make it more valuable and running it and answering the phones and collecting money from tenants, It's a business. It is a small business. There's people, there's management, there's hi…”
Nick Huber Dec 22, 2022 ▶ 2:15 How Nick Huber Built His Wealth: From Sweaty Startup to Real Estate Investor
Accounting data unlocks cross-selling for insurance, loans, and SMB services
“Accounting kind of cuts through a lot of the different Costs of a small business. We can see what kind of insurance you have. We can see what kind of loans you have. We can see what other services you use as part of managing your business. I think there is a r…”
Enzo Ottens Dec 16, 2022 ▶ 17:23 SMB Tax App hits $20k MRR by getting 1k+ Signups and Converting 20-50% to $35/mo paid accounts
Kozeski: Starting a nonprofit is no different from launching a small business
“Anyone that thinks that they're going to start a nonprofit and think it's simpler or any different than starting a restaurant or you know, an ice cream stand down the street is completely mistaken. They are starting a small business.”
John Kozeski Dec 7, 2022 ▶ 3:47 A Nonprofit Is Just a Business That Doesn't Turn a Profit
Sanchez: Buying a very small business is effectively buying a job
“And what I don't think people realize is that's buying a job. You're buying a job when you buy a company that small. And those types of deals exist all around this country. They're everywhere.”
Codie Sanchez Nov 22, 2022 ▶ 7:16 How Codie Sanchez Built a $50 Million Portfolio of Boring Businesses, and the #1 Skill to Learn in a Recession
Momand: Regulation, Not Small Business, Is the Backbone of the Economy
“People talk about the small business being the backbone of our economy. I actually think regulation is like the backbone of our economy, good or bad, sometimes even bad back.”
Maleka Momand Dec 22, 2021 ▶ 27:27 How to Fix Dysfunctional Government with Esper CEO Maleka Momand · Joe Lonsdale
Halasnik: Small businesses only have one chess piece to play during recessions
“You know, when you're a small business, okay, you have one chess piece. You don't have a lot of Options. You don't have a lot of moves. It's a real problem for a recession where like a small business, yeah, they can cut back on their costs really, really quick…”
Steven Halasnik Dec 22, 2020 ▶ 28:44 The Chess Board Secret: Why Small Businesses Only Have One Move
A vertical-agnostic strategy drove Ripl's small business SaaS growth
“Being a much more broad based and kind of agnostic as to which small business vertical we serve, it's really driven the growth.”
Clay McDaniel May 15, 2020 ▶ 4:03 1756 "Ripl Hits $10m ARR Helping 70k SMB's Create Video Content "
Hale: Startups are defined strictly by rapid growth
“For us at YC, the definition of a startup is a company that is designed or created to try to grow very quickly. So if you're not trying to build a company that grows very, very fast, ah, then you're just building a normal company. It's a small business.”
Kevin Hale Jul 25, 2019 ▶ 2:59 Kevin Hale - How to Evaluate Startup Ideas · Y Combinator
O'Shaughnessy: 4x Free Cash Flow Signals Distress in Public Equities, Not Private
“And, you know, when he first told me that he was buying businesses at a little bit north of four times free cashflow, you know, I kind of laughed. I thought, okay, like, so they're going out of business in three years. I mean, in the public markets, that multi…”
Patrick O'Shaughnessy Jun 10, 2019 ▶ 1:00:51 Patrick O'Shaughnessy – O'Shaughnessy Asset Management (First Meeting, EP.01)
Kellogg: SMB software requires a 'do-it-for-me' managed service layer
“Even if we had the greatest, you know, small business platform in the whole world for small business, there wouldn't be a lot of utilization without the service piece. We literally need to do the work for them. So we put together kind of the do it for me model…”
JB Kellogg May 17, 2019 ▶ 4:10 1392 $104m in ARR and Bootstrapped?!?! How?!
Sheehan: Live chat is too difficult for most small businesses to support
“Frankly, if you're open 40 hours a week, the majority of the time you're not available. And even when you are available during those business hours, it's very tough for a small business to support live chat.”
Drew Sheehan Apr 13, 2019 ▶ 4:41 1358 He's Put in $450k Before Turning on Paywall, Smart or Not?
10% to 15% of SMB churn is uncontrollable business failure
“In small business, you're going to have, to your point before, you're going to have 10 to 15% that are going to naturally go out of business.”
Kirk Simpson Mar 9, 2019 ▶ 7:35 1323 How FinTech Company Wave Is Deploying $100m in Capital, $25m+ in ARR
King: SMB software adoption is driven by trusted resellers, not product superiority
“One thing we've come to know is that all products, you know, that are pretty good is the small business is going to rely on the expertise of someone they trust and they're going to, you know, and in any given case, you could argue one product's better than ano…”
Brendan King Nov 26, 2018 ▶ 8:07 1220 How He Shields Himself from SMB Churn with 1200 Resellers, $2.3m/mo in Revenue
TOP FOUNDERS Assertion Supported
The Average Small Business Uses 14 SaaS Integrations to Operate
“I mean, if you look at the small business, the average small business has 14 integrations right now. They're using 14 SAS's just to survive.”
Dane Atkinson May 2, 2018 ▶ 13:08 1012 SquareSpace CEO Tried Acquiring First, Now King of SMB Data
Porat: Dun & Bradstreet lacks quality data on small businesses
“Dunbar actually does an awesome job at public companies and large private companies, but when you get down to the small business level, you know, they just don't have that great information.”
Sean Porat Nov 6, 2016 ▶ 5:58 EP 470: How He Got 10,000 Interested In Product Before Launch with Scorely CEO Shawn Porat
20VC Insight
Operating a Small Business Serves as a Mini MBA
“Working as a restaurateur or a small business owner in general, you know, I talk about small businesses are fantastic because ultimately full accountability rolls up to you, one person. You have to Ultimately develop a skill set. You have to be good at a lot o…”
Ryan Holmes Oct 28, 2016 ▶ 4:51 20VC: Hootsuite's Ryan Holmes on Optimising Productivity in Meetings, Creating An Ownership Culture & Lessons From Running A Pizzeria!

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