Small Businesses

topic on 26 shows · 85 statements across 71 episodes

Founder's Journal Startup Acquisition Stories In Depth More or Less Startups For the Rest of Us Cheeky Pint We Live to Build American Optimist the Knowledge Project Masters of Scale BigDeal My First Million the Neon Show No Priors the Official SaaStr Podcast Starter Story the Startup Ideas Podcast WTF is with Nikhil Kamath Capital Allocators Top Founders the MAD Podcast How I Built This the a16z Podcast Big Technology All-In 20VC

The latest 60 statements about Small Businesses, every show

BIGDEAL Assertion Not checkable as stated
Sanchez: Most small businesses are underpriced by 30% to 300%
“I basically went through thousands of small businesses over the last five years, and I analyzed all of their pricing. And I found that on average, most businesses are priced anywhere from 30% below or 300% below the price of what they should be selling for.”
Codie Sanchez Sep 10, 2026 ▶ 3:38 How To Ask For More Money (And Actually Get It)
TOP FOUNDERS Assertion Partly supported
European Small Businesses Employ Two-Thirds of the Workforce
“Considering that they employ like two thirds of the workforce in Europe, they create 85% of the new jobs in Europe, and still they don't have this kind of basic infrastructure of external financing to grow and do much more.”
Oliver Moseni Sep 8, 2026 ▶ 1:41 The Surprising Way This Startup Bank Makes Millions
Onboarding Micro-Borrowers Costs Banks As Much As Large Corporations
“For a bank to onboard such a customer is just as costly as onboarding a large corporation that's requiring several million.”
Oliver Moseni Sep 8, 2026 ▶ 3:14 The Surprising Way This Startup Bank Makes Millions
TOP FOUNDERS Assertion Not checkable as stated
Froda Has Financed 150,000 Small Businesses to Date
“So, so far we've supported a 150,000 small businesses and that's one of our super important KPIs.”
Oliver Moseni Sep 8, 2026 ▶ 5:58 The Surprising Way This Startup Bank Makes Millions
a16z Assertion Not checkable as stated
Overtoom: Hundreds of thousands of small practices handle billing manually
“There are, like, hundreds of thousands of these small businesses that literally, like, do this all by hand.”
Stein Overtoom Jul 29, 2026 ▶ 3:32 “Every small business should run itself” | Lassie with a16z
a16z Insight
Overtoom: All small businesses share the exact same core administrative workflows
“All small businesses at an abstract level, Like have a system of record they need to read and write into. They all have customers in doctor offices. They happen to be patients, but it's interacting and transacting around payments. You need to book appointments…”
Stein Overtoom Jul 29, 2026 ▶ 35:10 “Every small business should run itself” | Lassie with a16z
a16z Assertion Partly supported
Overtoom: 70% of small US healthcare practices are still paid on paper
“I think the stats are 70% are still paid on paper. And it's going through this massive, like, digitization revolution right now, because federal inflection point, that's regulatory.”
Stein Overtoom Jul 29, 2026 ▶ 53:54 “Every small business should run itself” | Lassie with a16z
AMERICAN OPTIMIST Prediction Not checkable as stated
Kaplan: AI will trigger an explosion in new small businesses
“I actually think one thing I'll go on the record on is I think there's gonna be an explosion in small businesses.”
Russell Kaplan Jul 9, 2026 ▶ 4:27 Why AI is Bigger Than the Industrial Revolution
Brown: There will never be enough buyers for retiring small-business owners
“And the Eureka moment was that look, this is a supply demand equation. They're just never going to be enough buyers for these businesses.”
Mike Brown Jun 17, 2026 ▶ 9:30 Teamshares IPO: $60M EBITDA, 92 Companies, Zero Exits · More or Less Podcast
Brown: Small Acquisitions Usually Need External Presidents for Financial Leadership
“In the smaller businesses sort of like up To a million or two. They're not generally someone who's ready to take on the financial responsibility for running the business. And that's why externally four out of five, three out of five businesses, you know, we ne…”
Mike Brown Jun 17, 2026 ▶ 14:36 Teamshares IPO: $60M EBITDA, 92 Companies, Zero Exits · More or Less Podcast
AMERICAN OPTIMIST Prediction Not checkable as stated
Melas-Kyriazi: AI Back-Office Automation Will Drive Explosion of Small Businesses
“I think what we're seeing now, which is really exciting is this explosion of small businesses getting started. And I think that people are going to be able to spend more time on what they're truly passionate about, probably spend more time on things that direc…”
John Milles-Kiriazzi Apr 17, 2026 ▶ 34:17 How AI Agents are Changing Investing · Joe Lonsdale
Fry: SMBs Should Use AI for Revenue Growth, Not Cost Cutting
“A lot of people think of AI and they think of cost cutting and they're like, oh, we can really optimize our P and L. We can use AI, automate all these jobs, cut costs. That's not the right lens to look at small businesses. And it's not right for really one rea…”
Will Fry Apr 9, 2026 ▶ 13:18 How to Turn $15K Into $1M in 2026 · Joe Lonsdale
AMERICAN OPTIMIST Assertion Partly supported
Lonsdale: 32% of Small Businesses Cannot Find Reliable, Punctual Workers
“32% of these businesses you're seeing, 32% of millions of businesses have a job opening, but they can't find someone who's willing to come and just work hard and show up on time.”
Joe Lonsdale Apr 9, 2026 ▶ 20:33 How to Turn $15K Into $1M in 2026 · Joe Lonsdale
AMERICAN OPTIMIST Assertion Not checkable as stated
Fry: Tech Workers Are Leaving Silicon Valley to Start AI-Driven Local Businesses
“And we've seen a lot of folks leave Silicon Valley and start new small businesses. So start from scratch using AI and absolutely clean up shop in their towns.”
Will Fry Apr 9, 2026 ▶ 22:05 How to Turn $15K Into $1M in 2026 · Joe Lonsdale
AMERICAN OPTIMIST Assertion Supported
Fry: Small businesses created two of every three jobs in past 25 years
“The past 25 years, two out of every three jobs have been created from small businesses.”
Will Fry Apr 9, 2026 ▶ 34:07 How to Turn $15K Into $1M in 2026 · Joe Lonsdale
AMERICAN OPTIMIST Prediction Open · timeframe Apr 2036
Fry: Small Businesses Will Create Over 80% of Jobs Next Decade
“I believe that in the next decade, they'll rise to four out of five, five out of six jobs.”
Will Fry Apr 9, 2026 ▶ 34:12 How to Turn $15K Into $1M in 2026 · Joe Lonsdale
AMERICAN OPTIMIST Prediction Not checkable as stated
Kaplan: AI will cause an explosion in small businesses
“One thing I'll go on the record on is I think there's going to be an explosion in small businesses. I think AI is actually like an extremely small business enabling technology in particular”
Russell Kaplan Mar 27, 2026 ▶ 47:15 How AI Agents Are Creating 12X Productivity Gains · Joe Lonsdale
AMERICAN OPTIMIST Assertion Supported
Loeffler: Small businesses drive 40% of GDP and create two-thirds of new jobs
“Well, that's right, on a GDP basis, and about the same amount from an employment rate basis, so small businesses create two out of every three new jobs, so it's incredibly, incredibly powerful economic engine for the country.”
Kelly Loeffler Mar 13, 2026 ▶ 1:53 Exposing a Billion Dollar Fraud Scandal (Using Palantir) · Joe Lonsdale
WE LIVE TO BUILD Assertion Not checkable as stated
Sadan: 50% of Duda's users were agencies outgrowing single SMBs
“We looked at our user base and about 50% were small businesses, but the other 50% were these web designers, digital marketers, agencies building websites on behalf of small businesses. And they, like, the data showed us that they were growing faster for us tha…”
Itai Sadan Jan 6, 2026 ▶ 23:05 65% of Their Sites Now Start This Way (Most Founders Miss It)
AMERICAN OPTIMIST Prediction Not checkable as stated
Lonsdale: One Million Small Businesses Will Change Hands as Boomers Retire
“I think there's actually like a million small businesses that are going to change hands because baby boomers are retiring right now.”
Joe Lonsdale Dec 30, 2025 ▶ 28:30 These Jobs Will Skyrocket in the AI Economy · Joe Lonsdale
BIGDEAL Insight
Sanchez: Distressed businesses are almost always fixable if leaders act fast
“And what I've found in investing in hundreds of businesses now, it's almost always fixable to your point. Almost always. But the reason it won't be is because you don't move fast enough. You don't have people who have been there before around you, and you don'…”
Codie Sanchez Oct 7, 2025 ▶ 21:35 Business Expert: The BEST Way To Make Millions In Profit | Mike Michalowicz
Collison: Small Shopify merchants outperform large retailers in e-commerce experience
“Thanks to Shopify, we are now, I don't think it's hyperbole to say we're living in an inverted world where the very large retailers are worse off in their e-commerce experience. They have, you know, worse systems and lower converting websites than Small busine…”
John Collison Oct 6, 2025 ▶ 20:09 Tobi Lütke is still captivated by internet commerce, 20 years later
Tolia: Nextdoor made a mistake delaying small business onboarding
“I think we probably made a mistake not thinking about how to bring small businesses into the conversation from the beginning.”
Nirav Tolia Sep 15, 2025 ▶ 50:55 Nirav Tolia: Nextdoor. How neighborhood chatter went global
a16z Assertion Not checkable as stated
Mark Cuban says a 15% tariff would wipe out small business margins
“You increase, you know, from a two and a half percent average tariff to a 15% tariff, that's their profit margin, and it's gone.”
Mark Cuban Sep 9, 2025 ▶ 55:13 Mark Cuban on the NBA, Cost Plus Drugs, and How to Fix Politics
IN DEPTH Insight
London: Non-tech small businesses are eager to talk to product builders
“You would be surprised how many people actually are excited to speak with technologists. Most people outside of Silicon Valley, like small businesses and real, you know, industry and people don't get to speak with technologists often that can build products.”
Tomer London Jul 1, 2025 ▶ 17:05 How Gusto built a $9.5 billion company by identifying a burning problem
BIGDEAL Assertion Contradicted
Sanchez: Only One in 11 Small Businesses for Sale Sells Annually
“If there are 11 small businesses for sale on a street, just picture like houses, one in 11 will sell in any one year period.”
Codie Sanchez Jun 23, 2025 ▶ 25:48 How I Built 12 Income Streams Without Tons of Cash
CAPITAL ALLOCATORS Assertion Partly supported
Baby Boomers Own Nearly 50% of US Small Businesses
“70 plus million baby boomers own shy of 50% of the small businesses, and a lot of them are retiring and don't have a succession plan.”
Josh Kopowitz Jun 12, 2025 ▶ 26:27 Josh Koplewicz – Flexible Capital and Creative Structures at Thayer Street (EP.451)
BIGDEAL Opinion
Codie Sanchez estimates that 90 percent of small businesses undercharge
“Our guess, well, Nine out of 10 small businesses under charge.”
Codie Sanchez Jun 2, 2025 ▶ 2:23 It's Boring, But It Will Make Even Beginners More Money
BIGDEAL Assertion Supported
Loeffler: Small businesses must receive about 23% of federal contracts
“The SBA also oversees government contracting. We have to ensure that small businesses get about 23% of federal contracts”
Kelly Loeffler May 14, 2025 ▶ 25:30 Billionaire Business Expert: How Small Businesses Can Get Money - SBA Head, Kelly Loeffler
BIGDEAL Assertion Supported
Loeffler: 99% of US manufacturing businesses are small businesses
“Most manufacturers, 99% of them are small businesses”
Kelly Loeffler May 14, 2025 ▶ 32:25 Billionaire Business Expert: How Small Businesses Can Get Money - SBA Head, Kelly Loeffler
Courtney: AI implementation agencies for small businesses will be highly lucrative
“I think a business that Probably a lot of people should start in the short term, maybe in the next three, like for the next three years that I think would make a lot of money if you know how to run a business is a business that helps other businesses, especial…”
Jonathan Courtney May 12, 2025 ▶ 34:47 The Golden Age of AI is happening right now (Here's Why)
BIGDEAL Insight
Vaden: Founders should eventually detach their personal brand from the core business
“The way that I think about it for small businesses is I think about it like a rocket. Is going your personal brand should be the sort of side boosters that you use to get the business off the ground. But then once you get it launched out, out, out into space, …”
Rory Vaden May 7, 2025 ▶ 54:56 Money Making Expert: How to Turn Attention into $$$
FOUNDER'S JOURNAL Assertion Supported
Only 30,000 out of 34.8 million US businesses reach $100M revenue
“There are 34.8 million small businesses in the US. While there are only 30,000 businesses, In the US that are doing at least a hundred million dollars in revenue.”
Alex Lieberman Apr 28, 2025 ▶ 14:50 A primer on seedstrapping
Tank: AI replaces 'non-usage' for businesses lacking support and sales lines
“And I think this is really more useful to kind of small businesses, which kind of replaces non-usage. Like, there is no support line for a small business. There is no, like, sales line, right? There is no pre-sales line, because they, you know, a small busines…”
Aytekin Tank Feb 25, 2025 ▶ 19:29 Hands On: Building Customer Service AI Agents — With Jotform's Aytekin Tank
a16z Prediction Not checkable as stated
Schmidt: Next PE era involves tech-automated small businesses acquiring rivals
“I see, like, the next evolution of private equity being possible where small businesses can leverage technology to basically, like, automate parts of their services organization and then go and use a better business model to acquire other small businesses.”
Joe Schmidt Dec 23, 2024 ▶ 0:15 AI-Powered Acquisitions: A New Playbook
a16z Insight
London: Accountant trust drives small business software adoption
“Accountants are a big part of the decision Process for small businesses often. And we, if accountants believe in gusto, then that can help their small businesses also believe in us.”
Tomer London Dec 5, 2024 ▶ 13:24 How Gusto Used Customer Input to Scale Growth with Tomer London
STARTUPS FOR THE REST OF US Assertion Contradicted
Orangio: SMB-targeting SaaS companies average 12% monthly growth in recent survey
“So if you were targeting small businesses, your average growth rate probably looked around like 12% month over month.”
Asia Orangio Jul 9, 2024 ▶ 21:11 Episode 721 | 7 Key Takeaways from the 2024 State of Independent...
Beshore: Roughly 80% of small businesses are unknowingly breaking government regulations
“My guess is 80% of the small businesses out there are either knowingly or should know that they're breaking some sort of rules.”
Brent Beshore Jun 11, 2024 ▶ 2:01:31 Brent Beshore: Business Brilliance and Happiness at Home
Beshore: A passive index of small businesses eventually trends to zero
“The reality is over a long enough period of time, that index is zero. Like it's really hard. The governance of these things is difficult. Like the norm for most small businesses is entropy is decay. Is dying a slow death and being wound down. Like that's a nor…”
Brent Beshore Jun 11, 2024 ▶ 2:03:07 Brent Beshore: Business Brilliance and Happiness at Home
SAASTR Insight
Chestnut: SMB Software Sales Pipelines Need to Span Five to 10 Years
“It's a little bit weird with small businesses because sometimes with small businesses, they need like five years to figure it out and you know how it is. And so. We never really found the one show. What we found was that they just need lots of time to find the…”
Ben Chestnut Jun 11, 2024 ▶ 6:09 Ben Chestnut: The Top 10 Learnings Scaling Mailchimp to $1B ARR
Buhrdorf: Banking and taxes are small businesses' top post-formation worries
“Banking for us is really about, it's one of the, it's the number one next to taxes is the number one thing that, that Small businesses are worried about, like, oh my god, I just did a formation, you know, what kind of filing do I, you know, what kind of format…”
Ross Buhrdorf May 21, 2024 ▶ 12:19 Want $100m in revenue? Copy these lessons from ZenBusiness CEO Ross Buhrdorf
MASTERS OF SCALE Assertion Supported
Clark: 65% of small businesses feel healthy, but distrust national economy
“We're just out of the field with this quarterly poll we do with MetLife. 65% of small businesses said they feel really good about the health of their business. 65%. That same group of people, only 32% of them, felt good about the health of the overall economy.”
Suzanne Clark Apr 26, 2024 ▶ 2:20 How optimism fuels the economy (U.S. Chamber of Commerce CEO Suzanne Clark) | Masters of Scale
Clark: Large and small businesses share identical core economic concerns
“To me, it's a little bit of a myth that they're that different. Their concerns are alike. Worker shortage, wage inflation, supply chain concerns. You know, you hear the geopolitical uncertainty. You hear the same concerns, no matter what the size of the busine…”
Suzanne Clark Apr 26, 2024 ▶ 3:06 How optimism fuels the economy (U.S. Chamber of Commerce CEO Suzanne Clark) | Masters of Scale
20VC Insight
Vickie Peng: Diluting Enterprise Products for Small Businesses Doesn't Work
“Diluting this product for this person is not going to work. Even if that's the most efficient path, it is not the most effective path.”
Vickie Peng Apr 17, 2024 ▶ 25:46 Vickie Peng: Why the Best Product People Actually Build Less Product? | E1141 · 20VC with Harry Stebbings
Giffon: Top Operators Would Outperform by Starting SMBs Rather Than Acquiring Them
“A lot of these businesses, I think if you just started them, you could really wipe the floor with the existing competition.”
Jeremy Giffon Apr 17, 2024 ▶ 26:07 Data Backed Businesses Guaranteed To Make +$1M From Day 1
TOP FOUNDERS Prediction Didn’t hold up
Schwartz: Upcoming 2025 regulations will force unprepared banks to lend to SMBs
“There's going to be some regulation coming out next year where banks are going to be forced to go back and start to lend out to the small businesses, but banks are not equipped to underwrite a small bit.”
Alex Schwartz Mar 21, 2024 ▶ 12:53 Miami Based Fintech did $70m in 2023 Revenue - What about Gross Margin?
IN DEPTH Assertion Supported
Cieri: Gusto serves over 300,000 small businesses evenly across industries
“So if you break down our customer set and we have north of 300,000 small businesses on Gusto now, And you look at them sort of by traditional industry segmentation, it's very evenly distributed across a lot of industries.”
Michael Cieri Feb 8, 2024 ▶ 14:58 Lessons from Gusto & Square on Finding Your Product Wedge | Michael Cieri
NO PRIORS Insight
Henry: Generative AI Unlocks Massive Small-Business Whitespace
“What's exciting about all this technology, you know, that's one example, but there's so many of these kind of different things where just the ease of use and the accessibility opens up what previously was effectively just massive white space, right? It was cus…”
Alyssa Henry Dec 14, 2023 ▶ 6:56 No Priors Ep. 44 | With Former Square CEO Alyssa Henry
Lieberman: Small Businesses Are a Bad Customer Base for Agencies
“The fourth is that small businesses are generally a really bad customer base. I think agencies that serve small businesses are the worst type of agency. I think the only companies that do well by serving small businesses are what I would call electricity, mean…”
Alex Lieberman Dec 8, 2023 ▶ 23:17 Weekly Recap: An Inspirational Entrepreneur, My Convos with Allstate & Activision, and Agency Lessons
Lessin: Sub-$20B businesses are shut out by both banks and venture capitalists
“Small businesses you know, things that aren't, can't be public company, twenty billion dollar public companies ever are very poorly served by everyone right now because banks won't lend to them. And you know, there's no capital for them and venture capitalists…”
Sam Lessin Nov 10, 2023 ▶ 50:41 #22: Your GPT Will Make More Money Than Your Substack? Please Tell Us More… · More or Less Podcast
Hodgson: Issuing Net-30 invoices makes small businesses interest-free lenders
“What you realize is small businesses lend more than they ever borrow, because that invoice that they sent that says net 30, that's essentially a free loan.”
Laura Hodgson Sep 12, 2023 ▶ 34:35 Stacey Abrams: How to harness risk | Masters of Scale
20VC Prediction Not checkable as stated
Sela: Small business failure rates will stay high without end-to-end ecosystems
“Until someone figures out how to build an end-to-end sort of ecosystem that changes the disadvantage that an independent has by being independent, I think small businesses, the failure rate will continue to remain high.”
Ilir Sela Aug 4, 2023 ▶ 36:18 Ilir Sela: How I Founded Slice Pizza & Became One of Macedonia’s Largest Employers | E1044 · 20VC with Harry Stebbings
WTF Assertion Supported
Aatrey: Only 1M to 1.5M of India's 60M small businesses sell online
“Very, very India has about sixty million small businesses, about million, million and a half only sell anything online.”
Vidit Aatrey May 7, 2023 ▶ 1:44:45 Ep #3| WTF is E-commerce: Kishore Biyani, Udaan & Meesho Founders Reveal What Sells and What Doesn’t · Nikhil Kamath
Smale: Small businesses sell on profit multiples, not revenue
“For most small businesses, so probably everyone listening, you generally don't get a revenue multiple. There's a lot of misinformation out there around valuations, but revenue multiples are uncommon. You generally get a multiple of profit.”
Thomas Smale Apr 17, 2023 ▶ 12:04 Zero to $1.1B from Flipping Websites
Beshore: Small businesses stay small because of removable operational bottlenecks
“Small businesses don't stay small on purpose. There's a reason why they stayed small. And usually there's some lids on the business that we're able to release over, over time that help the business grow.”
Brent Beshore Jan 26, 2023 ▶ 10:03 Mastering Micro Private Equity: Brent Beshore's Strategy for Wealth Generation
Sanchez: A good boring business needs 15% to 50% margins
“So I would say a good boring business is 15 to 50, 15 to 50% margins. 50 would be like really good. 15 would be like, okay, we've got a healthy business within lots of characteristics. One to three is awful.”
Codie Sanchez Nov 22, 2022 ▶ 28:50 How Codie Sanchez Built a $50 Million Portfolio of Boring Businesses, and the #1 Skill to Learn in a Recession
FOUNDER'S JOURNAL Prediction Not checkable as stated
Sanchez: Small business market will trend downward over 6 to 12 months
“I'd probably wait another six or 12 months and see what goes down. I'd like to spend a bunch of time learning about this stuff that I think is going to be super impacted. So for me, it would be like, I would learn deal making. I would learn to buy boring busin…”
Codie Sanchez Nov 22, 2022 ▶ 56:17 How Codie Sanchez Built a $50 Million Portfolio of Boring Businesses, and the #1 Skill to Learn in a Recession
Gazdecki: Bizness Apps refused to build enterprise functionality to stay strictly SMB-focused
“At business apps, we in our, you know, values, like you were saying, we said we serve small businesses, so we never built like enterprise functionality.”
Andrew Gazdecki Jul 12, 2022 ▶ 47:50 Startup Acquisition Stories with Lloyed Lobo - Founder of Boast.ai and Traction
STARTUP IDEAS Assertion Not checkable as stated
Katayev: Small Businesses Typically Sell for 3 to 5 Times Income
“In between for these small businesses, because they're typically sold at like three times, you know, three to five times income.”
Val Katayev May 26, 2022 ▶ 59:51 $30M by Age 19 — And Where You Should Build Today
STARTUP IDEAS Prediction Open · timeframe Jan 2032
Belsky predicts the number of small businesses will 10x by 2032
“And in 10 years from now, I think we're going to see probably 10 X the number of small businesses as there are today.”
Scott Belsky Jan 11, 2022 ▶ 1:06:24 Forecasting the Future of Tech with Scott Belsky | Where It Happens

← every entity, every show

Made with StarZero

Turn any episode into a week of clips.

This entire site, thousands of episodes across every show transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.