3 strangers showed us how they make $10M, $20M, and $30M/year

Introduction and Overview of the Conversation

• The companies mentioned have revenue of $10 million, $20 million, and $30 million per year, with the businesses being acquisition, management, and another unspecified business, generating significant revenue 10s.
• The setting of the conversation is unusual, with the participants noting that they are not used to being in person and are more accustomed to interacting through a screen, having previously recorded in a setting with red chairs bought from Amazon 42s.
• The conversation touches on the topic of bodega culture in New York, with one participant mentioning that they have to avoid bodegas because they tend to chat with the owners for too long, and another participant noting that bodegas are a great example of entrepreneurship 2m6s.
• The participants are introducing a special segment where they will be talking to three entrepreneurs who have unusual businesses, with the goal of showcasing the diversity of business opportunities and helping to open up the minds of their audience 4m10s.

Introducing the First Entrepreneur and Their Business

• The three entrepreneurs will be introduced, and they will share their business information, starting with a number, and then discussing their business and answering questions about adjacent business opportunities and how they can be helped 6m30s.
• The participants aim to learn more about the businesses and help the entrepreneurs by asking questions and providing guidance, with the goal of exploring new business ideas and opportunities 8m40s.
• The first individual, who owns 40 publications, generates $10 million in revenue from real estate advertising magazines, with each magazine featuring listings from a specific neighborhood and being mailed to residents based on property value and income 10s.
• The magazines, which are part of the company Haven Lifestyles, have between 100 to 200 pages and are used by real estate agents to promote their listings and attract new clients, with the goal of either gaining new listings or selling existing ones 2m6s.
• The idea for the magazine business started with the individual's business partner, Ryan, who had a small publication in Annapolis, Maryland, and was asked by agents to expand to other areas, such as Washington DC 4m42s.
• The company has been in operation for 10 years, with a slow but steady build in revenue, and currently has a profit of $2.5 million, although the size of the largest company in the space is not publicly known 8m10s.

Background and Growth of the Magazine Business

• The individual's background includes working as a bill collector for 5 years, which they believe helped with sales skills, before starting the magazine business with their college roommate and business partner 6m30s.
• The company's growth has had jumps, with the first year's revenue being around $300k, and has since expanded to cover the entire US and Canada, with 40 different locations or zones 10m0s.
• The business owner started by meeting with individuals and grinding it out, with their business partner handling other aspects of the company, and they initially thought they could make enough to support themselves, but not necessarily $10 million 10s.
• The owner launched an initial publication, a free version of the magazine, and had meetings with potential clients, with the first meeting resulting in a commitment, and subsequent meetings also being successful, leading to a sense that there was a viable business opportunity 1m5s.
• The magazine is not a subscriber-based publication, but rather a brochure-like magazine that is sent unsolicited to potential customers, with a huge portion of the business being driven online, and everyone paying to be featured in the magazine 2m42s.
• The company handles the artwork and design for the magazine, with most of the designers being based in the Philippines, and they print 30 different magazines a month, with each magazine being published every 6 weeks 4m10s.
• The company has 20 employees and mails out around half a million magazines per year, using the post office's business model, which allows them to target specific postal routes and demographics 6m30s.
• The business owner believes that it is possible to reach $100 million in revenue, but would need to expand and grow the company further to achieve this goal 10m30s.

Strategies for Scaling and Expanding the Magazine Business

• The discussion revolves around brainstormed ideas that are simple, relatable, interesting, and profitable, with a focus on how to grow a business from $10 million to $100 million, and one of the individuals involved has a goal to double their profit 10s.
• To achieve this goal, it's suggested to first determine the default growth rate, which in this case is 10% per year, and then consider ways to increase profit without necessarily growing the top line 2m6s.
• The individual's business involves sending magazines to people, specifically targeting real estate agents, and there's a discussion about exploring other verticals, such as home services, to expand the business 4m42s.
• The idea of reverse-engineering successful businesses in other industries is brought up, with the suggestion to look at companies that grow by mailing out informational materials to homes, such as wealth management companies or neighborhood publications like Stroll 6m15s.
• The conversation touches on the concept of creating a magazine that provides useful and entertaining information to homeowners, such as tips for home maintenance, while also featuring home service providers, with the goal of making the advertisement more valuable and less like a traditional ad 10m10s.

Operational and Market Expansion Considerations

• The individual is encouraged to consider new approaches to their business, but it's also acknowledged that they seem happy with their current situation and may not need to change their strategy 8m40s.
• The idea of hiring professionals to provide home care services is discussed, and it is suggested that getting familiar with the existing players in the space and learning from them could be beneficial 10s.
• The possibility of expanding the market from 40 to 80 is explored, with the idea of breaking down the existing 40 markets into smaller areas that could resonate more with customers 2m6s.

Psychological and Strategic Goals for Business Growth

• The topic of selling the business is touched upon, with one person expressing willingness to sell, but not necessarily having it as a goal, and another person finding this attitude surprising 2m6s.
• The importance of psychological aspects in entrepreneurship is highlighted, and it is suggested that setting specific goals, such as increasing net margins from 25% to 35%, could lead to significant changes and profits 2m6s.
• A goal is set to double profits within 11 months, with a target of reaching a $4-5 million run rate profit, and it is noted that improving retention rates could be a key factor in achieving this goal 2m6s.

Customer Relationship and Sales Process Optimization

• The strategy of pre-selling services to clients, such as offering discounts for long-term commitments, is discussed, and it is mentioned that around 1,500 people are already taking advantage of this option 2m6s.
• To improve customer experience, it's suggested to personally talk to the top 100 spenders to understand what they love, what they hate, and why they aren't doing more business, which can be done in 30 days 10s.
• Tiering key clients into categories such as tier one, tier two, tier three, and tier four can help define the quality of relationships, with tier one being someone who would do a favor, tier two being someone with an email relationship, and tier three being transactional 2m6s.
• The CEO of a successful business tiered out key clients and created definitions for each, resulting in a wake-up call when realizing most relationships were tier three or four, highlighting the importance of talking to top customers 2m6s.
• Using AI tools like Lindy can automate the sales process, respond to emails, and upsell customers, allowing salespeople to focus on customer experience and getting people to come back 6m34s.

Introducing the Second Entrepreneur and Their Campground Business

• The discussion involves various individuals, including Alex Daniels, who has an impressive AI setup, and Josh, who runs Team Outsider, with a focus on improving customer relationships and sales processes 10m34s.
• The business acquires family-owned campgrounds, with a projected revenue of around $20 million this year, and typically rents different spaces such as RVs, tent spaces, and cabins to people, offering amenities like stores, cafes, swimming pools, and lakes 10s.
• The campgrounds have various amenities, including stores, cafes where they sell ice cream, burgers, and pizza, cabins, swimming pools, lakes, and even a go-kart track at one of the locations, making it an outdoorsy hotel experience 2m6s.
• The most popular campgrounds are often located in tourist destinations, such as the one near Grand Teton and Yellowstone, and another one called the Neversink River Resort, located a couple of hours outside New York City 4m42s.
• The idea to buy a campground came from the founders' desire to start a business together, looking for a market with fragmentation, operational complexity, and a sense of meaning, where they could make a positive impact on the team members and customers 6m10s.

Growth and Investment Strategy of the Campground Business

• The founders, who met in college, currently own 16 campgrounds with around 4,000 sites across 10 states, and they raised money for their first purchase using their own cash and an SBA loan 8m20s.
• The first campground they bought, located near Yellowstone, was purchased for around $3 million, with the loan covering over 80% of the cost, and it was already generating around $500,000 in top-line revenue, with a cash flow of around 35% 10m30s.
• The founders' strategy involves buying existing cash-flow-generating campgrounds, often run by families looking to retire, and then improving their operations, such as implementing digital marketing, to increase revenue and cash flow 12m40s.
• The business strategy involves maintaining relationships with potential sellers and getting a call when they are ready to sell, with the goal of professionalizing systems, such as introducing digital marketing, better websites, and voice systems for phone training, to increase efficiency and profitability 10s.
• Digital marketing efforts include managing Google reviews and paid ads, as well as implementing digital reservation systems, which are often lacking in the industry 42s.
• The idea to invest in campgrounds originated from the founders' backgrounds in hospitality and real estate, combined with an avid RV'er's perspective, which led to a road trip to meet campground owners, team members, and guests, and ultimately sparked interest in the space 2m6s.
• The company has raised around $60 million and currently owns 16 properties, with a total worth of over $100 million, and has outside capital from family offices, accredited investors, and institutional partners 2m6s.
• The business operates on a promote-based structure, with a typical private equity setup, including a preferred return, return of capital, and a split depending on the investment partner, allowing the founders to generate personal cash flow and net worth 4m30s.

Operational and Cultural Challenges in the Campground Business

• The first campground purchase was a success, with the net operating income (NOI) doubling from $150,000 to $300,000, allowing the company to refinance and use the capital to buy the next property 6m20s.
• Campgrounds are an attractive real estate investment option due to their strong yield, operational complexity, which provides opportunities to drive value, and favorable depreciation characteristics, similar to manufactured housing 8m40s.
• The depreciation characteristics of campgrounds are attractive to tax-sensitive individuals, as the roads and infrastructure can be depreciated, and there is limited land value and building value in rural markets 10s.
• The goal is to continue operating campgrounds in the long term, with a focus on experience-oriented real estate, as businesses that bring people together in the real world are expected to become more valuable, and there is still a big pipeline of properties to be a part of 1m42s.
• There are two large REITs in the campground space that initially focused on manufactured housing but have recognized the potential of campgrounds due to similar infrastructure and depreciation perspectives 2m6s.

Acquisition and Management of Campgrounds

• When buying campgrounds, the operator is bought out, and a property manager is put in place, with the company acting as the manager, having initially thought to hire a third-party manager but deciding to build an OpCo to maintain culture and scale 3m30s.
• The company has a cool branding and is exploring the idea of creating a membership program, similar to KOA, which is a franchise with 550 locations across the country, and the company is actually a KOA franchisee in certain markets 5m20s.
• KOA is described as the "McDonald's of campgrounds," offering a brand that people can trust, with a consistent experience, and the company's campgrounds have a community-focused approach, with many seasonal guests who reserve a specific space for the duration of the season 6m40s.
• The business involves acquiring and managing campgrounds, which are often family-owned and have a strong sense of community, with the goal of building a trusted succession plan for the owners, who care deeply about their properties and the relationships they have built with their guests 10s.
• The day-to-day work involves writing handwritten letters, making cold calls, and checking up on potential sellers, with the challenge being to get in touch with and build relationships with the owners, who are often busy and difficult to reach, especially during peak season 2m6s.
• The business is focused on building relationships and being the trusted succession plan for the owners, who are looking for someone to take over their properties and maintain the high level of hospitality they have provided to their guests 4m42s.

Marketing and Branding in the Campground Industry

• The company is trying to figure out how to market itself in an authentic way, without being overly promotional, and is using various methods such as Facebook groups and conventions to reach potential sellers and build its brand 6m15s.
• The business requires a significant amount of work, with the owner estimating that they work a lot of hours per week, but they enjoy the challenge and are motivated by the goal of building a successful company 10m42s.
• The company has a large team of employees, with over 350 people working to manage the campgrounds and provide hospitality to the guests, and while some team members may not be the right fit, the majority are incredible and aligned with the company's mission 12m10s.

Company Culture and Employee Management

• The company's mission is to be the most hospitable team in the world, which is important when trying to replace a family-owned business, and the owner has had to deal with some challenging situations, including firing a convicted bank robber who was employed by the company 14m20s.
• The individual had a few unusual situations, including a drive-in incident and discovering that some team members were cutting down trees and selling the wood for cash on a Facebook page, which were outlier situations that were not representative of the norm 10s.
• The person lives in New York because their family, including their wife, son, parents, and in-laws, are all located there, while their business partner is based in Bozeman 2m6s.
• A burning question was posed about how to scale culture and keep hourly employees across 10 states incentivized to deliver a high level of service, with the goal of finding a solution that could be implemented quickly 4m10s.
• To address this challenge, it was suggested that studying companies that have already solved similar problems, such as Chipotle, could provide valuable insights, and hiring people who have experience working for these companies could also be beneficial 6m15s.

Examples of Strong Company Culture and Hospitality

• Chipotle's approach to building a strong culture, including naming general managers and providing incentives such as a $10,000 payment to employees who become general managers, even if they no longer work at the company, was cited as an example of a successful strategy 8m20s.
• The idea of finding "forgotten moments" to surprise and delight customers, as described in Will Guidara's book "Unreasonable Hospitality", was also discussed, with examples including a Ford car dealer who put a $15 Starbucks gift card in the glove box of every car, and a UPS store owner who rewarded employees for hospitable behavior with a $20 bill 12m30s.
• Brian, the founder of Autopilot, manages $1.8 billion and generates $30 million per year in revenue, with his company achieving this milestone in just three years, which is a testament to the demand for investing in retail traders 4m10s.

Introducing the Third Entrepreneur and Their Investment Platform

• Autopilot's success can be attributed to its innovative approach, including the launch of the Nancy Pelosi stock tracker on Twitter, which allows users to follow her stock picks and has shown significant returns, with Nancy Pelosi's portfolio being up around 240% in the last three years 6m20s.
• The platform enables users to follow and invest alongside various individuals, including politicians and hedge funds, with 13 hedge funds already on board, providing a track record of success and allowing users to make informed investment decisions 8m40s.
• Autopilot solves the chicken and egg problem of marketplaces by manufacturing the supply side, using publicly available information to kickstart the platform and attract users, with the goal of making anyone a potential hedge fund 10m30s.
• The company's approach differs from traditional Substack newsletters, where users can only follow content, but with Autopilot, users can follow and invest in the trades and portfolios of experienced individuals, providing a more transparent and performance-based investment experience 12m10s.

Business Model and Growth of the Investment Platform

• The company has raised about $16 million and has $30 million in revenues, with potential valuations between $300-400 million from venture firms, indicating a significant growth trajectory 10s.
• The founder of the company is 31 years old and started the business six years ago with an initial idea called Iris, which allowed users to see into other people's portfolios, inspired by their own experiences trading on Robinhood 2m6s.
• The concept of the company is to provide a platform where users can invest in high-risk, high-reward strategies by following successful investors, with the goal of finding someone with a track record of success to invest 10-20% of their net worth 4m42s.
• The idea is similar to Ray Dalio's approach, who started with a newsletter and eventually created his own fund, and the company is looking to replicate this model by allowing successful investors to launch their own portfolios on the platform 6m15s.
• The company has a 6,000-person waitlist to launch a portfolio on autopilot and conducts thorough due diligence, including analyzing the track record of success and actual portfolio of potential investors, to ensure legitimacy 8m30s.
• One of the most successful individuals to launch a portfolio on the platform is Peter Wolfe, who has seen a 200% return over three years, and the company has the technology to connect and analyze personal investment accounts, such as Robinhood 10m40s.

Revenue Model and Subscription Strategy

• The top people on the Autopilot platform are making around $1 to $2 million per year, which is outside of their stock trading, and this amount is earned through a subscription fee that ranges from $100 to $500 per year 10s.
• The subscription fee is similar to Substack, and the number of subscribers a person has depends on how much they charge, with an example being Peter Wolfe having around $220 million following him on Autopilot 2m6s.
• The Autopilot platform allows users to connect their brokerage account, such as Robinhood, and automatically follow a trader's fund, with the user's money remaining in their own account to avoid regulatory issues with the SEC 4m42s.
• The business structure of Autopilot has existed for 6 years, but the Autopilot platform itself has been running for 3 years, and the company is preparing for potential downturns in the stock market 6m15s.

Market Positioning and Future Outlook

• The retail investor is persevering longer than they used to, and in the event of a downturn, the company would need to adapt, with an example being Robinhood's near-death moment during the GameStop event when they had to raise $4 billion in emergency funding 10m10s.
• The Autopilot platform is changing the way people invest, with the potential for the next generation of investors, such as the next Bill Ackman or Ray Dalio, to come from the platform 8m20s.
• The current metrics of a company would be exciting for venture capital, especially with the AI wave and the fact that fintech was considered sexy in 2020 and 2021, and now the company has launched its own portfolios, taking 100% of the revenue, with a GMV revenue of $30 million and an autopilot ARR of around $22 million 10s.

Comparison with Traditional Asset Management

• Some fintech companies, like Wealthfront, can have billions of dollars in assets under management (AUM) but make relatively little revenue due to tiny fees, for example, $30 million in revenue, and this is similar to other traditional asset managers who put money in ETFs and mutual funds without trying to generate alpha 1m42s.
• The company's Autopilot service charges an average of 3 to 4% of AUM, which is higher than traditional asset managers, because the goal is to outperform the market, and this is why customers are willing to pay more for this service 2m6s.
• The company has had no direct interaction with Nancy Pelosi, despite having a portfolio named after her, and they have not received any cease and desist letters, but they did sponsor the UFC and hired a fake Nancy Pelosi as part of a marketing stunt 4m10s.

Marketing and Branding Efforts

• The marketing stunt, which cost around $450,000, involved sponsoring the UFC and having a fake Nancy Pelosi walk into the arena, but it did not directly help the company, although it did generate brand affinity and earned media, and the company is now trying to think of its next stunt 6m30s.
• The company currently has around 30-35 employees and is generating around $1 million in revenue per employee, which is a significant amount, and the company is trying to think of ways to scale and grow its business 10m30s.

Vision and Ambitions for the Investment Platform

• The idea of Autopilot is to allow users to automatically follow and replicate the investment portfolios of other successful investors, similar to how BlackRock's Aladdin tool works for institutional clients, with the ultimate goal of becoming the world's largest asset manager 10s.
• BlackRock's Aladdin tool generates around $6 billion per year and allows companies like Walmart to hedge their bets by investing in portfolios that offset their risks, and Autopilot aims to bring this technology to retail investors 2m6s.
• Autopilot is a two-sided marketplace where "pilots" can create and share their portfolios, and users can follow them, with the platform taking a cut of the revenue generated by these portfolios 4m42s.

Hiring and Talent Acquisition Strategies

• Hiring highly motivated people is a challenge, especially for senior-level positions, where candidates may be skilled at presenting themselves in a favorable light, and having a personal audience or network can be helpful in attracting top talent 6m15s.
• To find the right people, it's essential to have a clear understanding of what the job requires and what problems the candidate will need to solve, and writing down a specific job spec can help attract a more suitable candidate 8m10s.
• Using outside help, such as an outsider hiring committee or a buddy who is skilled at hiring, can also be beneficial in finding the right people for the job 10m0s.
• To improve hiring skills, it is helpful to have someone experienced interview favorite candidates and provide feedback, which can help identify weaknesses in the interviewing process and improve questioning techniques 10s.
• There are two good pools to hire from: people who have already solved the problem before and unproven talent, or "diamonds in the rough," who have the potential to be highly successful 2m6s.
• When hiring someone who has already solved the problem, it is essential to find someone who has specifically solved the exact problem before, not just someone who worked at a successful company 2m6s.
• Mapping out companies that have solved the problem before and identifying the key people involved can be an effective way to find talented candidates 4m30s.
• Building systems to consistently source candidates from both pools of people, experienced and unproven talent, is crucial for successful hiring 6m10s.

Operational and Growth Challenges

• The CEO of the business spends about 20% of their time per week on recruiting, which is approximately one full day a week, and believes that most founders who have hiring problems do not track the time they spend on recruiting 8m20s.
• The company is cash flow positive, with $30 million in revenue, and is expecting a growth rate of about 250% this year, which requires hiring a lot of people, including software engineers, product people, growth people, and marketing people 10m40s.
• Maintaining a high bar for hiring and being quick to let people go if they do not perform well is essential for the company's culture and success 12m50s.

AI and Productivity Enhancements

• The goal with AI is to make each person much more effective, so a good person with AI could be 10 to 20 times more effective than an average person with AI, and this is achieved by automating tasks and finding faster paths 42s.
• To be effective, one needs to be able to do the work of three people, which means being smart about what not to do and finding ways to automate tasks, and this mindset sets a different bar for the team on how they operate 2m6s.

Investor and AI Market Insights

• Leopold is considered one of the best, and he has made a significant amount of money, with his fund being around $5 billion, and he achieved this by identifying bottlenecks in companies like OpenAI and investing in areas like SSDs 4m6s.
• Leopold's success can be attributed to his smart investments and his ability to attract capital from friends and family, as well as smart money from investors like Gross and Nat Friedman, and he has also been able to gather information from his network, including someone who is the chief of staff at Anthropic 6m4s.
• Leopold published a white paper or blog post called "Situational Awareness" before launching his hedge fund, which outlined his bold predictions for the next 10 years of AI and attracted the attention of smart people and investors 8m10s.
• The publication "Situational Awareness" was a key factor in attracting capital to Leopold's fund, and it is also the name of his company or fund, and it is considered a valuable resource for understanding his perspective on the future of AI 10m2s.

AI Tools and Their Impact

• Victor, an AI tool, was used to break down a PDF into 10 key ideas, including predictions and hypotheses, and provided step-by-step explanations, which answered every question and was found to be very useful 10s.
• The AI tool, Victor, is so good that an investment was made in it, despite its absurd valuation, and it is now being used in every business 1m4s.
• A person, who is a very good friend of Orkesh, posts on Twitter and can be followed on Autopilot, where his top 15 picks can be replicated 4m14s.

Investment Strategies and Risk Management

• This person's investment picks are tracked with a 45-day lag, as they follow a 13F, which requires a fund size of $100 million 6m34s.
• It is suggested that people should invest 10 to 15% of their liquid net worth in high-risk, high-reward stocks or portfolios, such as those offered by Autopilot 9m14s.
• Autopilot allows users to follow model portfolios created by pilots, but it does not track their entire brokerage account history, only the history of the model portfolio from when the pilot joins 11m30s.
• Pilots on Autopilot, including the person being discussed, put their own money into their portfolios, providing "skin in the game" and verification of their investment strategies 13m4s.

Growth Trajectory and Future Goals

• Getting from $0 to $1 million in revenue was the hardest thing to achieve, but getting from $1 million to $30 million was relatively easier, with a goal to hit $100 million in revenue by March next year, and currently having a $70 million run rate 10s.
• The first round of valuation was $7 million in 2021, and the business has been scaling a lot since then, with the founder being a fan of the marketing strategies used by others, such as Chris, and reaching out to them to express admiration for their work 2m6s.
• The founder believes that marketing played a crucial role in their success, and they wouldn't be where they are today without it, and they also appreciate the opportunity to learn from others and pick up new ideas and strategies 4m30s.
• The conversation also touches on the idea that opportunity and success are not scarce, but rather abundant, and it's about finding the right fit and picking the right path, with the founder mentioning that they have learned from others and want to adopt certain traits, such as calmness, from people like Alex 10m0s.

Marketing and Community Building

• The founder also mentions the importance of being part of a community of like-minded individuals, such as the Hampton community, where interesting business owners can connect and learn from each other, and potentially be featured on platforms like My First Million 12m0s.
• The idea of admiring and learning from others without necessarily wanting to trade lives or replicate their exact circumstances is discussed, with examples of appreciating the creativity and success of individuals like Brian and Josh, while also acknowledging the differences in their approaches and goals 10s.
• The importance of being impressed by and learning from people with varying levels of success, whether it's a billion-dollar company or a five-million-dollar company, is emphasized, highlighting that all achievements are equally awesome and worthy of appreciation 2m6s.

Learning from Others and Embracing Diversity

• Jesse Itzler's quote about rooting for everybody and being able to never lose is shared, and a similar idea is applied to learning from others, suggesting that if you think you can learn from everybody, you can never lose, which is exemplified by looking forward to learning from someone like Ray Dalio 4m42s.
• The value of extracting useful insights and lessons from various interactions, whether with high-profile individuals or everyday people, is highlighted, with the suggestion of a new slogan "we get high high and low low" to reflect the equal joy and learning that can be derived from diverse experiences 6m15s.
• The conversation concludes with a reflection on the importance of being open to learning from everyone, regardless of their background or level of success, and finding value in the diversity of experiences and interactions 8m30s.