disclaimer: all business carries risk, don't take risks you can't afford.
Zero to One by Peter Thiel - about strategy
The Lean Startup by Eric Ries
Blue Ocean Strategy by Renée Mauborgne and W. Chan Kim - about strategy
Never Eat Alone by Keith Ferrazzi - about networking
The 4-Hour Workweek by Tim Ferriss - about efficiency and balancing business and enjoying life
Multipliers by Greg McKeown and Liz Wiseman - about leadership
Team of Teams by General Stanley McChrystal - about organizational behavior
The Art of the Deal by Donald Trump
Ah yes, the good stuff! I’m one of the few who encourage entrepreneurship while also supporting finishing college. Most well-paying jobs require a degree, and it’s tough to fund a business on a shoestring budget with low income if you can’t find investors. The good news is that successful entrepreneurs come from all backgrounds—some excelled in school, while others didn’t. A meme circulated claiming that school performance didn’t matter for success, featuring Bill Gates, Jeff Bezos, and Elon Musk—but Gates went to Harvard, Bezos to Princeton, and Musk to Wharton. All prestigious schools.
You may want to join a mastermind or hire a startup coach.
Attending a prestigious school can be beneficial if it's affordable, even if only part-time while building a business. If not, community college works as long as it's accredited. A bachelor’s degree is typically the best path.
The Trump administration removed the deduction for entertainment expenses, which is one policy I disagree with. Entertaining clients is a legitimate business expense, and hopefully, this will be corrected in the future.
Three things to know to enhance business ability: NL Texas Holdem Poker, golf & a foreign language (Spanish is the most spoken US 2nd language, German, Mandarin, Farsi, Japanese are all good choices as well; most of the world has large English speaking populations so if you don't speak English you should learn it especially if in an English speaking country.) A lot of business is conducted over the golf course and with people you meet in golf and poker; and even if they speak English they may appreciate that you know some of their language.
Owning a business has perks like writing off a new vehicle over 6,000 lbs, corporate jets, and even tax-free long-term capital gains on the first $10 million invested into private equity. Puerto Rico also offers major tax advantages, requiring a $10,000 annual charity donation, six months of residency per year, and homeownership within two years.
When I finished my MBA in Finance, I realized a business should be built for **scalability and resale value**, not just short-term profits. Keeping expenses low is crucial—imagine if you had $200K in earnings but paid yourself a $50K salary you didn’t need. When selling, that could cost you $1 million.
Some criticize the idea of selling a business, but most S&P 500 companies don’t last 20 years. If someone offers 10–20 years of profits at once, with a **20% tax rate**, it’s worth considering. You can reinvest, start another business, or take a break. A larger company may have better resources to scale, reducing costs and expanding market reach more efficiently than you could.
Don’t just start a business because it "might" make money. I focused on flipping signed Nolan Ryan rookies and Babe Ruth flip cards. When that market shrank, I tried other niches—86 Fleer basketball autographs, Desert Shield signed sets, and rare rookie autos. Most lost money, proving that not every niche works.
People have turned a few hundred dollars into millions flipping sneakers, but if I tried that, I’d lose my shirt!
Integrity is non-negotiable. If you lie to me once, we’re done. Trust builds long-term relationships.
“Loyalty is a two-way street. If I’m asking for it from you, you’re getting it from me.” —Harvey Specter (*Suits*)
“I hate a liar more than a thief. A thief is after my salary; a liar is after my reality.” —Curtis Jackson (50 Cent)
Ensure sufficient funding before starting. If a business will cost $250K–$1M, assume $1M is required. Avoid funding through personal credit cards.
Surround yourself with capable people. Recently, I met high school students excelling in management, media production, and entrepreneurship. These individuals could grow into trusted advisors or executives.
SBA loans are an option, but interest payments add capital expenditures. Equity funding may be better, even if it means sharing ownership. **Better to build wealth as a team than fail alone.**
Section 1202 is a **$2M tax-free gift**. If you invest in a company under $50M in assets and hold for 5+ years, capital gains (up to $10M) are excluded from taxes.
Even better—you can use this exclusion **multiple times** per year. Invest $1M annually in startups, hold for five years, and cash out $10M per business, **all tax-free**.
Alex Hormozi's Acquisition.com buys $1M of a $10M business and scales it to $100M. If he does this 10+ times annually, that’s a **tax-free path to a billion dollars.**
By relocating to Puerto Rico for **184+ days per year**, donating $10K annually, and owning a home within two years, you can **reduce tax rates to just 4%** until 2035.
your business and other peoples money (raising capital), your business and your money (bootstrapping), other people's business and your money (investing), other people's business and other people's money (running a fund.)
To start a moving business, you need either an extended bed pickup truck or a box truck (if you have a pickup truck, that can be your only vehicle; but it gives lots of options for earning money.) You may need insurance, you may do the work yourself or hire people; $300 for a simple moving job is on the low end of prices.
Lawn mowing, this used to be a job for a neighborhood kid; but they don't seem to be the ones mowing anymore. You need a truck realistically, but it's an easy way to make $35-50 for 30-60 minutes of work.
Wedding videography-Get a high end camera for $1000 if you're a skilled camera man and you can charge $1500 per wedding (first one might be $500 on the condition you be allowed to show samples as examples of your work), that's almost $300/hr; because you will also have to spend time editing the video. It's a great side business since lots of weddings happen on weekends.
If you're a skilled golfer with good communication skills, you can teach golf for $60/hr.
Digital Marketing AgencyFor 15 years I've gone from seeing the occasional person doing this to it being a very popular way to make money, if you work hard at marketing the service and know how to run an ad campaign well; you can make good money at it. The way to start is offer the service at $500/month the first month and $1000/mo after, that's not total that's on top of the actual marketing (ie Facebook ads, Tiktok ads etc) once you get 8 recurring clients, start offering the service for $1000/mo the first month and $5000/mo after. It's very realistic to get 1 client a week really working hard, you'd have a $100k business in 8-12 weeks. Day 1 of each new campaign would be 2-12 hours, then maybe 1-2 hours a day the next week, less than an hour a day towards the end of the first month and probably an hour a week in month 2+. The 2 skills you need to develop are how to market the service (generate qualified leads of businesses with the decision maker email, write an email, talk to them on the phone) and actually running ad campaigns (creating simple ads, putting the ad together on the platform, adjusting based on results.) Once you have a $100k business, you want to turn it into a $1 million a year business; at $5k/mo that's only 17 clients (maybe you look for a month to find each one, in 20 months you've gone from $0 to a million/yr in profit; as there's no cost in hustling.) If you want to make it more valuable without adding clients, some marketing agencies add a 20% premium to their adspend or get a discount of 20% on adspend if the rates are public knowledge the later works better but only for niche platforms that allow marketing agencies to do that (Facebook, Google, Tiktok may not offer agency discounts on their ads; that's often an older marketing strategy that may not work anymore but it's always worth trying even if you pass on the savings to the client.) Really, getting good clients and retaining them is more important than making money on upsells.
Vending machines- These can be bought used for $600 (maybe less) or new in the 2000-5000 range but if a decent location lets you put it there you can get around $200 a week, and those are at cheaper rates. If you get 10, that's about $100k/yr.
Laundromat- For about $50,000 you can start a laundromat in a strip mall, ideally one not far from apartments that either don't have their own washers/dryers or not enough or not very good; also far enough from other laundromats (though I know 2 laundromats that are practically neighbors, both still do okay.) A laundromat like this can earn $50k a year after expenses, not bad for a couple hours a week removing coins; just set it up to be low risk (might need metal gaurds on dryers to prevent damage, as it's cheaper than hiring an attendant.)
PMB (mailboxes & shipping center): One lucrative and scalable small business idea is opening an independent mailbox and shipping store. You can become an affiliate with carriers like DHL, USPS, UPS, and FedEx, earning a small margin on each package you ship. The main revenue driver, however, is private mailbox rentals. A location with 150 to 275 small boxes at $15/month, 60 to 90 medium boxes at $25/month, and 10 to 15 large boxes at $35/month, at 90% occupancy; can generate $44,000 to $74,000 per year in mailbox revenue alone. Add another $40,000 to $60,000 annually in shipping profits and $36,000 to $120,000 from printing and other services like notary, passport photos, and packaging supplies. Startup costs include leasing a location (around $3,000/month or more), business insurance, commercial grade printing equipment, mailboxes, and a secure interior buildout. In the early phase, expect to work long hours often 60+ hours per week until you cover startup costs and stabilize cash flow. As the business grows, you can hire trusted employees and eventually expand. With 2 to 3 well run locations just far enough apart not to compete, you could earn $180,000 to $360,000 annually in almost passive income, simply by checking in each evening. Some owners even hire managers from day one, depending on trust and capital. Either way, this model offers a reasonable return of $60,000 to $120,000 per location per year for hands on operators, with long term (modest, local) scalability. Lisa Song makes Youtube videos on these, she says she makes $300k/yr (not sure if that's for 2 locations or each) and only spent $60k to start them (both up within 45 days.)
Buying businesses-You might find a self service car wash for $700k with $100k down that makes a profit of $100k/yr, in a year you've covered your cost (though you have to make sure that $100k profit includes debt service on that 600k loan, if it's less; you have to look at the numbers and make sure it makes sense.) In a scenario where after tax profit is $100k, in a year you buy a second car wash, a year later you might buy 2 car washes; or diversify into other businesses. Some businesses that make $100k annually in profit sell for $300k with no real estate, the reason being that the owner no longer wants to run it and if they close down they get nothing. You might get them to stick around for 2 years and train the manager for $50k a year on top of a $300k note they agree to. You can google 'Business broker' and google will often find business brokers in your state or city that often list all of the businesses (along with revenue, profit if any, type of business); within a few minutes I found laundromats PMB business, roofers with profits (the first 2 were under $40k for a money losing business, if it's a good location it might work for a turnaround expert.)
Real Estate Broker If you become a real estate agent, after 2 years of being active you can take the course and take an exam to become a real estate broker. Being a broker equates to leverage, you have office expenses (it can be a high profile storefront or minimalistic office space, as long as it fits legal requirements) and it's no longer the lucrative 50/50 split it once was; but it's still a good business to be in. You may bring them top quality training and incentives, a better split to lure top agents from other firms; etc.
Imagine working in mowing and moving businesses and saving enough for 10 vending machines, and then a year later starting 2 laundromats. You could hire someone to collect the money for you (ideally a married middle aged former military, or a trusted relative; these tend to be the most trustworthy people for handling your money-as you know if your relative is trustworthy) and then maybe you still make $150k of that $200k and no longer have to work mowing lawns (maybe outsource it and have 10 guys mowing 3 yards a day each for $120/day and you make $300/day off your share for another $100k+ and maybe have 3 moving trucks doing 6 moves a week each where you make $100 after the workers get their share off each ride that's nearly another 100k. So, if you wanted these 4 businesses (probably a mower and mover isn't a cameraman, but that's also possible) and taking in $350k with no work on your part and creating 23 jobs that may go to college students and people who want a job that doesn't take over their life but makes decent money in a few hours work. Some other ideas include pressure washing ($500 set up), mobile oil change (it's costing $50 in shop these days, might pay that without having to leave the house), car detailing, cleaning short term rentals (like air-BNB, better repeat business), cleaning solar panels (you simply drive a neighborhood and anytime you see solar panels you give them a flyer.) The idea is to find something that covers your expenses in 1-2 hours a day or less, then makes money to pile up; finally has money to put into businesses that can pay for other businesses. Owning a chain of laundromats within a region could be a hefty payday if you went to sell, I know if you buy up a couple dozen funeral homes there are hedge funds that will pay a premium for the portfolio that wouldn't buy a single funeral home.
At this point, you can sit back and enjoy or take it further. You can buy businesses like laundromats, service businesses, franchises (one of the hardest to justify, a McDonalds Franchise can cost millions when you include the money the franchisee pays for construction of a building they don't even own), real estate, stocks. Personally, if I went this route (labor businesses, vending machines, laundromats); I would probably put profits into stocks (probably sp500 low fee index fund) as the rest are just added stress and none of these are things I'm passionate about. An interesting point of view I heard, you don't need to love your business; save the things you love for when you're not working. An example of this is someone who loves to go fishing might not love being a commercial fisherman, a leisure activity becomes work. If you take a salary of $100k and invest the rest within a corporation, you'll have $275k after corporate taxes (your 100k would be taxed separately) and can invest long term and allow those gains to compound and only pay the 21% corporate tax rate (or applicable taxes of the day if they change) on gains "if" you sell until you eventually close out positions and take it as a dividend that has a 15-20% tax rate.
Machiavelli warned that leaders must either be kind from the start or firm from day one. Flip-flopping leads to failure. Kindness works best for competent employees, while underperformance may require a stricter approach.
Maslow’s hierarchy of needs can help managers understand employees’ motivations. Recognizing where someone struggles—security, belonging, or self-actualization—allows tailored support. Great bosses balance **firm leadership** with **inspiring motivation**.
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