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My First Million

Every Business I Tried Before Making My First Million

Published November 17, 2025
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About This Episode

Sam walks through roughly ten different companies and side projects he tried before making his first million at around age 31, sharing how much money each made and what he learned from them. The conversation covers early hustles like flipping sports equipment, running a hot dog stand, selling white whiskey online, organizing an Anti-MBA book club, building a roommate-matching app, launching niche products like poison ivy treatment, and eventually creating The Hustle and this podcast. Along the way, Sam and Sean discuss developing money-making skills, scrappiness, project selection, risk reduction, and how entrepreneurship is largely about enduring uncertainty and fear over many years.

Topics Covered

Entrepreneurship Bootstrapping Persistence Personal development Copywriting Project selection Risk and uncertainty Side hustles Scrappiness in business

Disclaimer: We provide independent summaries of podcasts and are not affiliated with or endorsed in any way by any podcast or creator. All podcast names and content are the property of their respective owners. The views and opinions expressed within the podcasts belong solely to the original hosts and guests and do not reflect the views or positions of Summapod.

Quick Takeaways

  • Sam tried around ten different businesses over a decade before making his first million, using each as a learning experience rather than a final destination.
  • His earliest wins came from simple arbitrage and flipping, like reselling seniors' sports gear and discarded college items on eBay and from storage units.
  • Running a hot dog stand taught him sales, persuasion, and the value of copywriting as a scalable way to "sell" without standing in the heat.
  • Gray-area and quick-money schemes (like online moonshine and poison ivy treatments) made money but clashed with his values and long-term goals, so he abandoned them.
  • Sam's core money-making skill became copywriting and online marketing, paired with tenacity and a willingness to be extremely scrappy.
  • Over time he realized project selection is crucial: avoid illegal or unscalable manual-labor businesses and look for "forgotten" opportunities with weak competition.
  • He frames entrepreneurship as the ability to tolerate fear and uncertainty for 5-10 years while seeing little progress, continuing to move forward anyway.
  • Sam deliberately minimizes risk by bootstrapping, pre-selling, studying proven models in other industries, and doing deep research before committing.
  • He now favors small, serious, high-ticket events and durable, hard-to-disrupt businesses over flashy, rocket-fuel growth that often explodes.
  • Both Sam and Sean emphasize that the "come up" years are chaotic but uniquely fun, and that success often comes down to learning fast across many attempts.

Podcast Notes

Framing the episode around failures before the first million

Sam sets up the theme of reviewing roughly ten failed or mediocre companies

He wants to focus on the companies he started that mostly "sucked" before his first big financial success[0:03]
He plans to explain how much he made with each idea and the key lesson learned[0:11]

Clarifying the podcast name and Sam's first million

Sean states the podcast name explicitly as "My First Million" and asks when Sam made his first million[0:24]
Sam explains his first cash million came when his wife's Airbnb equity paid out at IPO, followed soon after by selling his own company[0:28]
They estimate he made his first million around age 31 and agree to walk through all the businesses he tried before that[0:45]

Early flipping hustles and the hot dog stand

High school sports equipment flipping on eBay

Sam's first online money came from reselling graduating seniors' sports equipment[0:59]
• He bought or was given old track spikes and other gear by high school seniors and flipped them on eBay
• He made about $2,500 one summer in high school from this activity
He notes that most of the time he did not even pay for the gear; people were happy to give it away[1:22]

College reselling and textbook arbitrage

Sam continued a similar model in college by collecting items people would otherwise throw away at move-out time[1:43]
• He stayed a few weeks after the semester ended, offered his storage unit, and asked people to leave items with him instead of trashing them, then resold the items
Sean describes classmates who did textbook arbitrage in a similar way[1:59]
• These people collected unwanted textbooks at the end of the year for free and later resold them to students who needed the same books, turning each into a $40-$50 future sale

Starting the Southern Sam's hot dog stand

At about age 20, Sam started a hot dog stand called "Southern Sam's. A wiener's as big as a baby's arm"[2:06]
• He rented a cart from a man named Doc, who allowed him to pay rent at the end of the month instead of upfront, reducing his initial capital requirement
• With roughly $500, Sam bought Vienna sausages and other supplies from Restaurant Depot and was in business within a week of having the idea
A neighbor named Rydell, who had served 20 years in prison for attempted murder, became his best friend and worked the stand with him[2:37]
• Sam emphasizes how close they were, saying Rydell had a spare key to his house and they spent all day outside running the stand
Income from the stand varied widely depending on the day and location[3:16]
• Some days he made as little as $50, while busy outdoor concert locations could bring in around $1,000 in a day

Balancing college classes with the hot dog business

Sam ran the stand while attending college, structuring his day to fit both[3:03]
• He worked the stand until 3 p.m., then went to classes from 3 p.m. to 8 p.m., and later operated a night session from 9 p.m. to 1 a.m. near bars
He was inspired to start the hot dog stand after seeing a video about Home Depot hot dog vendors allegedly making about $100,000 a year[3:26]
• Sam describes himself as broke but "in" after seeing that claim, joking that he had a "PhD" meaning poor, hardworking, and driven

Lessons from the hot dog stand: sales and copywriting

Sam would not repeat the hot dog stand now because the work was so hard, but he values what it taught him[3:41]
• He learned to sell by wheeling and dealing, schmoozing, and flirting with customers to increase sales
This offline selling experience inspired him to pursue copywriting as a way to scale his selling ability online[3:52]
• He realized he could write something once on the internet and have many people read it, instead of physically selling all day in the heat

Developing charm and social skills as a business asset

Concept of "flirting with everyone" and being "chalant"

Sean references a viral tweet encouraging people to "flirt" non-sexually with everyone as a way to be playful and charming[4:19]
• He describes this as practicing a social muscle that can turn routine errands, like grocery shopping, into more fun experiences
Sean says he has been experimenting with this approach and finds it "kind of amazing"[4:53]
They joke about the phrase "nonchalant" and coin the idea of being "chalant"-trying hard and being intentionally engaging[4:56]

Example of playful communication with a wealth manager

Sean shares an email he sent to his Morgan Stanley wealth manager about a large trade commission[5:07]
• Instead of complaining, he jokingly asked if there was a "magic button" to make the fees disappear
The wealth manager replied playfully, saying the magic button was pushed and commissions reversed[5:25]
Sean uses this story to argue that being playfully "flirtatious" with everyone often yields better outcomes than being passive or hostile[4:19]

Gray-area online businesses and lessons about alignment

Selling white whiskey ("moonshine") online

Sam started selling white whiskey packaged in mason jars online from Tennessee[6:00]
• He notes that while "moonshine" technically means illegal whiskey, legal companies were selling similar products and calling them moonshine
He attempted to structure it as a novelty or gift item, believing that might keep him within legal boundaries[6:08]
After making about $10,000 in roughly 30 days, he sought free legal advice from his university's entrepreneurship program[6:17]
• The legal advisors told him he needed to shut the business down immediately due to regulatory issues

Marketing tactics for the whiskey business

Sam got customers by posting on forums and message boards whose users were already interested in that whiskey[7:33]
• He targeted motorcycle forums and benefited from high early Google rankings for searches related to the product

Values misalignment and "gray hat" entrepreneurship phase

Sam describes this period as his "gray hat" phase, where he chased quick money in borderline areas[6:57]
• He realized he did not even like alcohol and had a love-hate relationship with drinking, so selling whiskey did not align with his values
His lesson was that if you pursue something regulated or sensitive, you must do it properly and ensure it aligns with your values[6:45]

Moving to San Francisco and building the Anti-MBA Book Club

Relocating to San Francisco and losing an Airbnb job offer

Sam moved to San Francisco for a job at Airbnb, but the offer was rescinded when they discovered he had lied on his resume about a DUI[8:46]
Finding himself in SF without a job, he focused on meeting people[8:54]

Creating the Anti-MBA Book Club to build a network

Sam started the Anti-MBA Book Club and tried to monetize it but initially could not[8:55]
• He posted ads on Craigslist, Reddit, and Facebook and got around 2,100 people to sign up to his email list
The premise was to replicate the networking benefits of elite schools like Stanford and Berkeley without an actual MBA[9:14]
• They read one book a month, broken into four weekly sections, and each week Sam brought in an expert on the book's topic for discussion
About 20 people came each week, and several became close friends and important relationships for Sam[9:37]
• He mentions specific attendees like Cieva and Neville, the latter eventually becoming the best man at his wedding

Book selection and learning approach in the club

They read books like Tim Ferriss's "The 4-Hour Workweek" and similar business titles[10:11]
Sam used the club as a forcing function to educate himself about business[10:23]
• He read each week's section in advance, took detailed notes, and effectively taught the material because most attendees did not read the book
• He secured a free venue in an arcade on the condition that attendees would play skee-ball there

Roommate-matching startup and early tech lessons

Joining a roommate matching app called Bunk

After moving to SF, Sam met someone building a roommate matching app and asked to join the project[10:43]
• He sold his pickup truck from Nashville, contributing about $5,000, which combined with his partner's money to fund the startup
The product, called Bunk, was positioned as a roommate-matching party website[11:03]
• They approached landlords with multi-bedroom units and advertised a three-bedroom as if it were a one-bedroom at one-third the price to attract many potential tenants
• They planned to host parties where prospects could meet, form groups, and move into that apartment or others

Outcome and misalignment with actual user behavior

They struggled to monetize the app, and Sam notes that roommate matching is a stereotypical, often-failed business for recent graduates[11:32]
After about nine months, the team was acqui-hired, which meant they received jobs and some bonus money tied to certain goals[11:39]
They discovered many users were using the platform to date rather than find roommates[12:02]
• Sam reflects that pivoting to a dating app like Tinder would probably have been smarter given the observed behavior

Three components of winning in business: skills, scrappiness, and selection

Identifying a money-making skill

Sean says winning in business requires a money-making skill that drives value, such as selling, making things, or finding deals[12:18]
He asks Sam what skill he was developing across his early projects[12:33]
Sam identifies copywriting and marketing-specifically getting website traffic and converting visitors-as his core skills[12:50]
• He also mentions tenacity and "getting after it" as complementary traits to the technical skill of copywriting

Becoming tenacious and scrappy

Sean describes tenacity and scrappiness as something people discover out of necessity when they have no other choice[13:04]
• Once you find that "gear" under pressure, you realize you can call on it in future situations, which changes your willingness to take on challenges
He notes nobody actually wants to be scrappy, but being forced into it reveals an "animal" inside that you can rely on later[13:12]
Sam adds that people often start scrappy, become a bit fancy, and then later rediscover the value of staying scrappy even when successful[13:41]
• He cites Amazon's small-team "pizza rule" as an example of institutionalizing scrappiness for performance reasons

Contrasting offices to illustrate scrappiness vs. fanciness

Sean recalls that when they met, his office was extremely lavish while Sam's was tiny and barebones[14:18]
• Sean's office had a massive custom redwood table, four stories, an in-office apartment with heated floors, one-way mirror walls, a chef, a masseuse on Fridays, and open bar
Sam's office was essentially a shared apartment with odd quirks, minimal amenities, and even lacked proper Wi-Fi while he built an internet company[14:35]
Despite appearances, Sam was building something that people wanted, while Sean felt he was "making things nobody wanted" in his fancy environment[16:05]

Project selection and process of elimination

Sean frames the third key as selecting the right projects and learning, via elimination, which businesses are bad bets[16:13]
• Examples of eliminated categories include physically exhausting, unscalable manual labor (e.g., hot dog stand) and illegal or high-regulation businesses (e.g., moonshine)
He says Sam was clearly in an "elimination phase", learning by trying and discarding various models[16:32]
Sean asks what criteria Sam now uses to decide if a project is good after all those experiments[17:11]

Ikigai, forgotten businesses, and Sam's project criteria

Using Ikigai and revenue potential as filters

Sam says he believes in the concept of Ikigai: what the world wants, what it will pay for, what he is good at, and what he is passionate about[17:14]
Beyond that, he adds a quantitative filter: can he bootstrap the idea to $100 million in revenue within 10 years?[17:30]
• He emphasizes the requirement that it must be bootstrappable, not dependent on heavy external funding

Targeting "forgotten" or underrated business types

Sam likes to study businesses similar to Hampton that quietly generate hundreds of millions in profit[18:13]
• He researches by talking directly to owners and doing due diligence to understand the underlying models
He prefers opportunities that serious operators or "ballers" do not take seriously, which keeps competition weaker[18:33]
• He cites The Hustle and Morning Brew as examples of newsletter businesses that many dismissed but which had clear paths to large revenue if you "do the math"
He also focuses on business types that are hard to disrupt, and says the rise of AI made this criterion even more salient[18:10]

Sean's observation of Sam's research-driven approach

Sean praises Sam for being very detailed and "chalant" in his research despite his nonchalant persona[19:31]
He notes Sam talks to bankers, ex-CEOs, and many players in a given space to understand how businesses really work[19:16]
Sam says he does this to "eliminate the uncertain" as much as possible before committing[19:45]

Entrepreneurship as managing uncertainty and fear

Long periods of unclear progress

Sam views entrepreneurship as largely about how much uncertainty and fear you can tolerate while continuing to move forward[19:56]
He notes that entrepreneurs often work 6-24 months on the same thing and still see little progress[20:03]
• The potential payoff-freedom, a sustainable business, or a big outcome-may take 5-10 years to realize
He lists recurring fears: hiring when finances are tight, responsibility for employees' families, serving first customers well, and dealing with public criticism[20:24]

Risk vs. uncertainty and entrepreneurs as risk minimizers

Sean cites Manish Parai's distinction between risk (what you stand to lose) and uncertainty (not knowing the outcome)[21:23]
He says stock market investors hate uncertainty and discount for it even when actual risk isn't high[21:07]
Sean argues that entrepreneurs are generally not big risk takers but rather "risk minimizers" who try to win while taking the least necessary risk[21:38]

Risk reduction example: Richard Branson starting an airline

Leasing a plane instead of buying

Sean recounts how Richard Branson started his airline by calling a major airline and asking about unused planes[22:02]
• Branson discovered they would lease him an unused 747, which reduced his need for upfront capital compared to buying a plane
The airline business model allows tickets to be sold before the operator has to pay for the plane and fuel[23:01]
• Branson minimized downside because if it failed he could return the leased plane; if it worked, early ticket sales would validate demand

Parallels to Sam's risk reduction tactics

Sean notes Sam similarly tries to reduce risk by choosing models with demonstrated demand in other contexts[23:29]
• Sam looks for spaces where there is weak or little competition from top-tier operators
He prefers to bootstrap without external investment so that the main thing at risk is his time[23:53]
Sam pre-sells as much as possible, including selling sponsorships before fully building products, to validate demand and fund operations[24:14]
Sean labels Sam a "master risk reducer" whose ideas may sound random, but are carefully chosen to maximize odds of success[24:27]

More experiments: poison ivy treatment and the long learning arc

Itch Juice: poison ivy treatment business

In 2015, Sam started a poison ivy treatment business called Itch Juice[25:29]
He discovered a mechanic's green scrub lotion that had the same ingredients as poison ivy treatment[25:30]
• He bought it in bulk as a barrel at around 20 cents per ounce and resold it branded as poison ivy treatment for about $20 per ounce
He was able to rank well on Google and the business started to make money[26:00]
However, he realized this was another short-term, get-rich-quick scheme that lacked alignment with his deeper goals[26:12]

Ten-year journey to understanding good businesses

Sam says it took him 10 years to figure out what constitutes a good business for him[27:22]
He and Sean discuss feeling "slow to develop" compared to seemingly mature and smart founders in their mid-20s[26:55]
• Sean says that at 26-27, he felt like he "knew nothing" and even now sees younger founders behaving in ways he still does not
Sean observes it took him a decade to stop just drawing frameworks on a whiteboard and actually execute like Sam was doing[27:20]
They emphasize that 10 years feels like an eternity in the moment, especially because you do not know when or if progress will pay off[27:34]

Uncertainty, the Lewis and Clark analogy, and the role of delusion

Lewis and Clark as a metaphor for entrepreneurial journeys

Sam compares entrepreneurship to Lewis and Clark being sent from St. Louis to walk west and report back what they found[28:03]
• He highlights they had no communication back home, took two years, and nobody knew if they would return, mirroring founder uncertainty
He says entrepreneurship feels like walking into the unknown for an unknown duration, hoping something good is at the end[28:40]

Need for self-delusion and supportive environment

Sean notes each year entrepreneurs tell themselves "now I know", only to later realize how little they knew, creating a cycle that requires some delusion to persist[29:40]
He argues that moving to San Francisco helps because you are surrounded by success stories and similarly deluded peers who normalize continued risk-taking[29:07]

Additional small projects, real estate, and event business lessons

Quick rundown of smaller experiments

Sam mentions the Frisco Disco Taxi, where he and others dressed in disco outfits with afros and gave rides on New Year's Eve, making about $800[29:34]
He ran a copywriting class with Neville, hosted at Sean's office, which brought in around $10,000 total or per person (he is not certain which)[29:53]

Real estate investing realization

Sam bought some real estate and learned that success in that field comes from doing heavy due diligence and looking at many properties[30:07]
• He concluded that real estate rewards people who "make their money when they buy", which does not match his personal skill set or style

The Hustle, Trends, and events business mistakes

The Hustle evolved from a conference to a blog and then to a newsletter, which worked well[31:17]
They launched Trends as a separate product, which Sam describes as fairly successful[31:28]
They expanded into events and learned their model was flawed[31:58]
• They hosted events with hundreds or thousands of people, but in hindsight he believes it is better to host smaller groups and charge much higher prices per ticket
• At the time, he could not imagine people paying $2,000-$5,000 for a trade show ticket, but now sees that model as superior

Building the My First Million podcast as a scrappy project

Origins and early revenue of the podcast

Sam says they did not initially think of the podcast as a business[31:31]
He started it alone, Sean joined a few months later, and it made very little money early on[31:33]
• For about the first nine months it effectively made zero or very little revenue, aside from a small sponsor that brought in roughly $10,000-$20,000

Lance Armstrong cameo and extremely scrappy setup

Around six months in, Lance Armstrong used Sam's office for a meeting and they pulled him into a recording[32:08]
• A photo from that day shows Sam, Lance, and Sean, but only two microphones and two chairs, so Sean had to perch on the arm of Sam's chair and lean into his mic
On another episode with a remote guest, Sam and Sean shared a single pair of AirPods between them and may have recorded on an iPhone[32:54]
They copied the bright red chairs from the "Fighter and the Kid" podcast set to stand out visually, even though they were very early and rudimentary in video[33:18]
• They bought a video camera at Best Buy and had an intern film a straight-on shot of the two of them, inspired by another show featuring Theo Vaughn and Brendan Schaub

Nostalgia for the "come up" and advice to younger founders

Reflecting on the fun and chaos of early years

Sam says revisiting these stories feels nostalgic and crazy given everything they tried[34:19]
Sean says that during those years, he desperately wanted something-anything-to work so he could escape the grind[34:35]
In hindsight, he realizes he has never had as much fun as during the "come up" period, which was unpredictable and full of quirky projects[35:04]
• He notes he would never now make time for things like Frisco Disco Taxi or the hot dog stand, even though they were fun and produced great memories

Encouragement for people in their 20s

Sam addresses younger listeners, saying many life-changing businesses have emerged from their peer group over the last decade[35:54]
He believes that if someone works hard for about 10 years and keeps taking risks, success is very likely, even if not always a "home run"[35:40]

Learning rate vs. individual project success

Sean says at the time you think success is about the current idea, team, and execution, but personally it's really about your rate of learning[36:20]
He invokes a "rule of 100": try 100 times and make one thing better each time, making eventual success almost inevitable[37:30]
He contrasts his own mistake of building things nobody wanted with Sam's pattern of always making things people did want, even if the models were flawed[37:56]
• Sean lists hot dogs, whiskey, itch treatments, and other products as examples of Sam consistently serving real demand

Real-time lessons Sam wishes he had internalized earlier

Sam recalls The Hustle's growth milestones (e.g., 100k in year one, 500k in year two, 1M in year three) and how it still felt like pushing a rock uphill[38:50]
He compared himself unfavorably at the time to Ryan Hoover's Product Hunt, which seemed to have clearer product-market fit and buzz[38:56]
He now sees he did have product-market fit but failed to recognize and fully optimize it in the moment[39:36]
Sam once believed he needed to "act corporate" to become a big company, but now believes you should act small as long as possible[38:41]
• He also now sees 50% annual growth as excellent and warns that chasing much faster growth, like some peers did, can lead to blow-ups

Rocket fuel vs. car analogy for funding

Sam cites a line that venture capital is like rocket fuel and rockets are the only thing that deserve rocket fuel[39:12]
He notes most rockets blow up, whereas a great car that you love can still reach the destination more slowly and reliably[39:28]
He admits he wanted rocket fuel and a rocket that worked, but in reality he wanted a good car and should have had the confidence to embrace that path[39:12]

Closing reflections and tease for Sean's version

Summarizing Sam's pre-million journey

Sean wraps by saying they focused on Sam's 10-15 attempts and stumbles leading up to his first million at 31[39:46]

Preview of next episode about Sean's failures

He plans to do a similar episode next time, outlining his own terrible ideas before he "finally made it"[39:58]

Lessons Learned

Actionable insights and wisdom you can apply to your business, career, and personal life.

1

Treat early ventures as experiments to learn skills and preferences, not as final destinations, and expect that it may take many attempts over a decade to understand what a good business looks like for you.

Reflection Questions:

  • • What past projects or jobs can I reframe as experiments that taught me skills, rather than as failures?
  • • How could recognizing a 5-10 year learning horizon change the pressure I put on my current project to succeed immediately?
  • • What is one concrete skill I can deliberately practice and track across my next three projects or initiatives?
2

Develop a specific money-making skill (like selling or copywriting) and combine it with extreme scrappiness so you can create opportunities even with minimal capital or support.

Reflection Questions:

  • • Which of my current abilities most directly create value or revenue, and how can I double down on sharpening that skill?
  • • In what areas of my work or business am I avoiding being scrappy because it feels uncomfortable or beneath me?
  • • What is one experiment I could run this month that forces me to use my core money-making skill in a scrappy, constrained environment?
3

Project selection is as important as execution: avoid illegal, unscalable, or misaligned ideas and instead seek "forgotten" niches with weak competition that you can bootstrap and that fit your values.

Reflection Questions:

  • • Looking at my current or planned projects, which ones clearly violate my own criteria for scalability, legality, or values alignment?
  • • How might I identify a "forgotten" or underrated opportunity in my industry where strong operators are currently ignoring the space?
  • • What specific filters (e.g., alignment with values, bootstrappability, revenue potential) can I write down and apply before saying yes to my next idea?
4

Entrepreneurship is largely about tolerating prolonged uncertainty and fear while continuing to move forward, so building emotional resilience and a supportive environment is a strategic advantage.

Reflection Questions:

  • • Where in my current work do I feel the most uncertainty, and how am I currently responding to that discomfort?
  • • How could changing my environment-people, location, or community-help normalize long-term risk-taking and persistence for me?
  • • What small, repeatable ritual could I adopt to remind myself that uncertainty is a feature of the journey, not a signal to stop?
5

Great entrepreneurs minimize risk rather than seek it by pre-selling, copying proven models into new contexts, bootstrapping, and doing deep upfront research to "vaporize" as much uncertainty as possible.

Reflection Questions:

  • • In my current project, what are the biggest assumptions I'm making that I could validate through pre-selling or small tests?
  • • How could I borrow a business model that already works elsewhere and adapt it to a niche or geography with weaker competition?
  • • Before investing more time or money, what specific research conversations (with customers, operators, or experts) should I schedule this month to reduce my downside?
6

Align your businesses with your long-term interests and values instead of chasing quick-money, gray-area schemes, because misaligned ventures will eventually drain your energy or force you to quit.

Reflection Questions:

  • • Which parts of my current work feel subtly misaligned with what I actually care about or enjoy?
  • • How might my decisions about products, customers, or industries change if I required them to align with my values for at least the next 10 years?
  • • What is one small pivot I could make in the next quarter to move my work closer to the intersection of what I'm good at, what I enjoy, and what the market will pay for?
7

Staying small and scrappy longer can be an advantage; you don't need to "act corporate" or pursue rocket-fuel growth if a solid, steady-growing "car" business can reliably get you to your destination.

Reflection Questions:

  • • Where am I mimicking big-company behaviors (process, overhead, optics) that don't actually serve my current stage or goals?
  • • If I optimized for durability and profitability instead of speed and hype, what decisions would I reverse or avoid in my business?
  • • What is one concrete way I can simplify my operations this month to preserve agility and scrappiness without sacrificing quality?

Episode Summary - Notes by Kendall

Every Business I Tried Before Making My First Million
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