There’s an idyllic notion that once you’ve sold your company for multi-millions of dollars you’re filthy rich and never have to work again. I admittedly have this automatic mindset whenever I meet someone who said they sold their company to one of the tech giants. Even if they are still living in a one bedroom apartment with their wife years after the sale, I just think they are being frugal.
By also believing everybody makes 10X more than the value of their car based on my 1/10th rule for car buying I’m able to keep motivation high to work harder since even a Toyota Corolla driver is clearing $200,000 a year nowadays. The goal is to give into the illusion of wealth in order to eradicate self-entitlement.
There is startup fever here in the San Francisco Bay Area partly because of all the stories we hear about 1,000 bagger returns in companies such as Google, Facebook, Instagram, Twitter, Tumblr, AirBnB and more. Sure beats investing in stodgy dividend stocks doesn’t it? Real estate is on fire and it seems like everybody in their 20s and 30s are tech millionaires. Given we have a culture of stealth wealth in San Francisco where you can’t tell a rich person from a poor graduate student, the possibility is real that your unassuming neighbor is rolling in the benjies.
The fact of the matter is that the vast majority of startup founders never make it past year three and even less sell for multi-millions of dollars. Even if a founder sells her company for $30 million dollars to Apple, she probably could have done better working a day job all those years instead, with much less stress!
In this article I’ll share with you a very insightful conversation I had with a man who ended up selling his company for tens of millions of dollars circa 2010 three years after business school (Should I Get An MBA?). You’d think as a 30-something year old, he’d just be kicking back on his own private island somewhere blogging right? Not so at all. But before we go through this fella’s example, let’s go through one of my favorite business assumptions first.
A LIFESTYLE BUSINESS OR A CHANCE AT MEGA MILLIONS?
In 2010 I asked everyone in a post entitled, “The Comfortable Lifestyle Business Or The Big Payout”:
Would you rather make $15-000-$30,000 a month and “work” only 2-4 hours a day? Or, would you rather make minimum wage working 12-14 hours a day for two years with a 25% chance of selling your business for $100 million dollars and netting yourself a cool $25 million? If you don’t, all you are left with are your experiences.
The answers were pretty mixed based on the comments (cut the numbers in half if you don’t live in Manhattan, SF, LA, HK, London, HK, Paris, Amsterdam). The reason why I asked this question back then was because I was already beginning to formulate my exit strategy from my job on Wall St. I had been working for 11 years and had just started to get a taste of the online business world and its potential. Given I was tired of working 12+ hour days, I opted for the lifestyle business instead.
I never really questioned my decision because money is a means to an end, namely a better life. Working 12 hour days for another several years sounded very unappealing because I already amassed a livable passive income stream. Fast forward to today and I’ve somehow managed to achieve my lifestyle business goal.
It’s interesting how the mind works once you put things down in writing. Your goals become tangible, thereby increases your potential for success. I had completely forgotten about this business dilemma until I met the potential client. I didn’t ask how much he sold his company for back in 2010, but it’s safe to say anywhere between $20 to $40 million dollars based on his feedback.
I asked him the very same question I asked all of you three years ago, and he unequivocally selected the lifestyle business to my surprise! Here’s a guy who sold his company for around $25 million dollars after just five years of operation and is choosing a $180,000 – $360,000 a year lifestyle business instead. I asked him to elaborate further as to why.
THE MATH BEHIND SELLING A MULTI-MILLION DOLLAR BUSINESS
Let’s say you successfully sell your internet startup to Google a mere five years after founding for $25 million dollars. You probably worked 14-16 hours a day everyday, but at least you were working on your baby. Here’s a typical way of how to get there based on my client’s experience for those who aren’t familiar with the startup world.
Step 1: It’s the year 2005 and after working on your brilliant idea for one year, you raise $1 million in Angel money in exchange for 10% of the company. Getting a $10 million valuation is a huge accomplishment in just 12 months of operation. You can’t just suddenly value your company at $10 million without large user and revenue growth so you must be doing something spectacular. You and your equal partner are left with 90% ownership.
Step 2: Grow your business to the point where you raise your first venture round of funding for $3 million in exchange for 25% of the company. You want the $3 million to acquire more users and solidify your company’s market share through more marketing. You and your partner are left with 65% ownership.
Step 3: Hire employees to help build your business further. By the time this person’s company was sold, he had a staff of 40. Give total equity of 20% spread across 40 employees as incentive and part of their compensation package. You and your partner are left with 45% ownership.
Step 4: Raise another $3 million at a slightly higher valuation in exchange for 20% of the company. Business is now booming and spending is a must to keep up and beat the competition. The company is not profitable yet, hence the need for cash to stay alive. You and your partner are left with 25% ownership.
Step 5: Competition is very intense and it’s the year 2007 where everything is just going up, up, up! Raise another $4 million for a 10% stake as business is expected to keep growing at the current pace for the next several years. Your company is now worth about $40 million! You and your partner are left with 15%.
Step 6: It’s the year 2010 and the worst of the financial crisis is over thank goodness.You sell your company as early investors and employees want out. You’ve found a buyer for $25 million, which is much better than $0 if you sold at the end of 2008 or 2009 because nobody wanted to buy an EBIT negative business. At one point the business could have been worth $60 million if you timed a sale perfectly. 10% of $25 million is still $2.5 million. Your stake is worth $1.25 million before tax since you have an equal partner.
Step 7: Your accountant advises you to take a 33%, 33%, 34% payout of the $1.25 million over three years to minimize tax liability. Meanwhile, given you worked at a startup, you made at least $50,000 a year below market for five years in exchange for equity upside = $250,000 opportunity cost. All told, your proceeds after taxes is about $900,000.
If you take into consideration the $250,000 in lost income you would have made working for an established firm, you really only net about $700,000. $700,000 – $930,000 is not chump change after five years of work. But remember, the $900,000 after taxes was distributed over three years after he sold. It’s very difficult to build a huge business by yourself. You need a team of people to help you get there.
During the five years of creating the business he went through enormous stress, relationship breakups, employee arguments, and countless meetings with investors. He appreciates the experience but he would never do it again. His biggest mistake was raising too much money and therefore giving too much of his company away. When things are booming, it’s easy to have the urge to spend, spend, spend since valuations keep on going up. He’s now started a new Y-combinator company and is being much more careful with fundraising. He’d rather not raise any money at all!
START A BUSINESS AND HUSTLE ALREADY!
My client reminded me that if you successfully build a lifestyle business, then you should have more than enough time to go for option #2, the home run business. Given I only have to work 1-4 hours a day on Financial Samurai (writing content, responding to inquiries, networking, etc), I can spend the rest of my time building another business or consult for several SF Bay Area financial tech companies that match the Financial Samurai value proposition.
I started Financial Samurai in 2009 I’m actually earning a good passive and active income stream online now. The top 1% of all posts on Financial Samurai generates 31% of all traffic. In other words, after putting in the hours to write some very meaty content over the years, 10 posts consistently generate a monthly recurring income stream that’s completely passive.
I never thought I’d be able to quit my job in 2012 just three years after starting Financial Samurai. But by starting one financial crisis day in 2009, Financial Samurai actually makes more than my entire passive income total that took 15 years to build. If you enjoy writing, creating, connecting with people online, and enjoying more freedom, see how you can set up a WordPress blog in 15 minutes like mine with my step-by-step tutorial.
You never know where the journey will take you!
Recommendation For Leaving A Job
If you want to leave a job you no longer enjoy, I negotiating a severance instead of quitting. If you negotiate a severance like I did back in 2012, you not only get a severance check, but potentially subsidized healthcare, deferred compensation, and worker training. Since you got laid off, you’re also eligible for up to 27 weeks of unemployment benefits. Having a financial runway is huge during your transition period.
Conversely, if you quit your job you get nothing. Check out, How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye, on how to negotiate a severance. I first published the book in 2012 and have since expanded it to 180 pages from 100 pages in the 3rd edition thanks to tremendous reader feedback and successful case studies.
Updated for 2020 and beyond. The lifestyle business is clearly the way to go. As they say, the best time to plant a tree was 20 years ago. The second best time to plant is today.