Things To Consider Before Selling Your Business (Baby)

As an entrepreneur, you create something from nothing. That something becomes your baby. It's so much a part of you it's practically all you think about 24/7.

But, there may come a day when you're approached about selling your business. Or perhaps you've run yourself into the ground and are dreaming about selling your business to finally feel free again.

Whatever the case may be, there are many important things to consider before selling your business. It's certainly not a decision to rush.

Savvy buyers will tell you everything you want to hear, making it sound like their offer is bullet proof. Don't be foolish and sign all of your equity away without first consulting an experienced attorney and your accountant.

In general, I don't think it's ever a good idea to sell your cash cow. If your business is making a tremendous amount of cash, hold onto it for as long as possible. Otherwise, you might regret selling your business, even if you sold it for millions.

Sometimes Not Selling Your Business Is Best

One of my luckiest investment decisions was not selling anything during the 2008-2009 financial crisis. I just held on for dear life, continued to max out my 401(k) and squirreled away anything left into an online savings account or CD.

In 2012, I got lucky again by receiving zero offers for my SF primary residence. Facebook just went public, but nobody wanted to buy my home. As a result, I held on, paid down more of the mortgage, earned some rental income, and then finally sold it five years later for 68% more. I probably should have held on.

In 2015 and in 2018 I passed on selling Financial Samurai. To sell before realizing my goal of writing 3X a week for 10 years would have made me feel like a quitter.

Then in August 2018, Google had a large algorithm update that has since boosted organic traffic by 50%. That was an unexpected upside surprise, especially since the site has been around since 2009.

Even after I reached my 10 year milestone, I kept on going. and I also received more offers about selling my business in 2019 and 2020. But, the fit and terms weren't right so again I passed. I'm not giving up my baby to just anybody.

It sure seems like the secret to creating wealth is to consistently save, invest, grow, hold and build for the long-term. Almost every significant wealth event in my life has taken at least five years to stew.

More Good Fortune Not Selling My Business

Four years later, I've already gained back in net profits what I would have sold Financial Samurai for in 2018. Now, everything is just gravy.

Further, if I had sold Financial Samurai in 2018, I wouldn't have been offered a handsome book deal by Portfolio Penguin, one of the most prestigious business imprints in the publishing world.

My new book, Buy This, Not That, ended up becoming an instant Wall Street Journal bestseller. As a result, it brought greater branding to Financial Samurai and more profits. Now I've signed a multi-book deal with Portfolio Penguin that goes through 2026.

If you can attach bestselling books to your business, your business becomes even more valuable. You're building an entire ecosystem of media around your business. Less than 0.3% of all books get on a national bestseller's list.

Buy This Not That Book Reviews

Things To Consider Before Selling Your Business

We know there are three main sources of wealth: 1) your job, 2) your investments, and 3) your business. Most people erroneously focus just on their job. Savvier people focus on one and two.

But to really build next level wealth it's worth doing all three. Start a business, own as much of the equity as possible, grow the business, and reap all the rewards.

Being an employee is fine. It's just that without equity, it's really hard to get very wealthy. You're essentially working to make someone else rich.

You don't have to build a big business. A small one that provides joy and boosts your overall income by just 10% is fine too. Over time, you just never know how large your business might grow if you stick with it.

If you've started a successful company and are thinking about selling your business, here are some questions and considerations to go through before letting go of your baby. I've shared my thoughts after each point as I consider retiring for a second time.

1) An attractive valuation

You must consider the valuation multiple compared to the overall S&P 500 and companies in your space. You must also consider the payback period and your likelihood of lasting beyond the payback period if you don't sell. The stronger your expected future earnings growth, the higher the valuation multiple you should demand.

Wise public companies buy promising private companies at lower valuations. If a public company is trading at 20X earnings, it should buy private companies trading at lower earnings multiples with higher growth rates all day long. If it does, each acquisition will automatically be earnings accretive.

My thoughts:

I don't want to sell Financial Samurai because I think valuations are too low for private media businesses. Let's say I'm offered 6X operating profit. This pales in comparison to the average 22X multiple for the S&P 500.

After six years of simply maintaining operating profit, I will have covered the entire purchase price. But every year after six years would be pure gravy. The payback period when all is recouped is also the point of serious regret for many entrepreneurs who sell. 

Further, if I can actually grow operating profit instead of let it stay stagnant, it makes even more sense to hold on. 

Example Of A Business Offer

For illustrative purposes, let's say someone offers me $6 million based off 6X operating profit of $1 million. If I can grow operating profit by 20% a year, the operating profit will have grown to $2.49 million after five years.

In other words, I would have ended up only selling my business for 2.4X operating profit, which would be like getting mugged in a dark alley! And if I ended up selling for 6X operating profit five years from now, I could get $14.94 million instead of just $6 million. Plus, there’s all the money I would have made over the five years as well.

The only way I'd ever sell is if someone offered me at least 12X operating profit due to consistent earnings growth and my ability to keep on going for at least five more years. You'll have to make an assessment on what's the right valuation for your business. 

2) Cash generator or money loser.

You either have a business that is losing money, but hopefully growing at a fast pace or you have a cash generating business that is usually growing at a more steady pace. If you have a money-losing business that isn't growing, then you need to sell ASAP.

A money-losing business is unsustainable over the long term unless the business can continuously raise money from outside investors to fund operations.

Uber, is a great example of a fast grower that lost $1.8 billion in 2018. Yet, because they are able to raise ~$9 billion from its IPO, the company should be able to fund its operations for at least five more years given its losses are shrinking (lost $2.2 billion in 2017). The company still hasn't returned much to shareholders in 2023.

If you have a cash cow business, then selling in a low-interest rate environment as we have now is a much harder decision to make. The reason is because a much higher capital amount is needed to generate a specific amount of income.

Look at the chart below. It shows the different amounts of capital needed to generate $55,000 and $20,000 in annual income at different interest rates. By a significant margin, cash cows are much more valuable today than they would be if interest rates were higher.

Never sell your cash cow in a low or declining interest rate environment

My thoughts:

The core costs to run Financial Samurai include server cost, e-mail software cost, random website maintenance cost, and my time. Depending on how I value my time, operating my website results in 70% – 98% operating profit margins. In comparison, Apple's operating profit margin is roughly 28% and Microsoft's operating profit margin is roughly 31%. 

Huge operating profit margins is one of the main reasons why everybody should start their own website. There is little downside if you fail, except for your time and maybe a little ego bruising.

It's not like you have to come up with a million dollars to start a restaurant to pay rent, remodel a space, buy food, and hire staff. A website is just you and your own creativity. 

Given I believe interest rates will stay relatively low for the rest of my lifetime, the value of owning a cash cow should also stay high for the rest of my lifetime. Business that couldn't get shut down during the pandemic have gone way up in value. Everybody wants a defensive cash cow business that's online.

3) Your personal goals

Do you want to sell for a profit or build a legacy? If your desire for maximum profits is strong, then selling your business may make more sense if you get the right offer. If you desire to build a long-term business because it gives you purpose and joy, then selling your business makes less sense. Decide what your personal goals are for your business.

My thoughts:

I didn't start Financial Samurai to make money. I just needed an outlet to address my fears during the financial crisis. Instead of smoking or drinking heavily, I decided to write.

I think you can tell that I enjoy writing, otherwise, I wouldn't author practically all of Financial Samurai's content. If I hated writing, I would hire a bunch of freelancers to write lots of product review posts to try and maximize my revenue. But so far, I haven't.

My purpose for Financial Samurai is to have a creative outlet to share my thoughts on a weekly basis. It feels good to get thoughts on paper and hear different perspectives from the community. To be able to formulate an idea, put it in writing, and releasing it to the world is very gratifying. 

Keeping It In The Family

A new goal is to run Financial Samurai long enough to teach my kids about online media, communication, and entrepreneurship. As an overrepresented minority at top universities, I assume it will be tougher for them to get in.

I assume they will also get discriminated against in the workplace due to an underrepresentation of minorities in leadership positions. Therefore, it's nice to have an insurance policy to skip university and the matrix all together. Here are my thoughts on Affirmative Action as an Asian American, even though it's been struck down.

They might have zero interest in learning about online media, but at least I can talk to them about the importance of creativity, consistency, and work ethic. A small business has many of the same departments as a large business e.g. finance, marketing, sales, production, etc. 

Finally, what a wonderful way to communicate with family and friends long after I'm gone. I remember replaying over and over an old voicemail recording of a middle school friend who shockingly passed away in a car accident. If I were to die today, at least my wife and kids will have hundreds of recordings and thousands of articles to go through.

4) Your view of the future

Do you see your business growing or fading? Can you create different products or revenue streams due to the strength of your brand? What are some new technologies that might disrupt your existing business? Are you capable of adapting?

Businesses fade away all the time. The murkier the future, the more you should consider selling.

My thoughts:

I've always believed that if you can build a brand, your business will do even better in the future. Think about how many different business lines Virgin is in. Richard Branson has built an incredible, edgy brand that has enabled him to get into music, transportation, hotels, and more.

Financial Samurai is a fierce brand in the personal finance space that digs deep into the numbers and provides no BS analysis and answers. Everything is written based on firsthand experience because money is too important to be left up to pontification. Well over 100 million people have visited Financial Samurai since the site started in 2009.

By establishing a brand that goes against the status quo (e.g. engineer your layoff vs. quit), plenty of new products can be created to leverage the brand. With only one book, I've barely gotten started on the business aspect of things. Now that my brand is established, I truly believe the opportunities are endless.

I envision a future where the consumption of online media via mobile devices only continues to grow. I see opportunity for Financial Samurai to expand internationally, especially in Asia and Europe.

Written content will never go away. It is by far the fastest way to consume information. Audio and video will continue to grow, and these are mediums I can easily utilize. I'm now building the Financial Samurai podcast brand. I'm confident it will grow to something significant over the next 10 years.

Here are some reflections of making money online since 2009.

5) Will the money change your life

You can't fault someone for wanting lots of money. If selling your business can significantly change your life for the better, then selling is absolutely an attractive decision. If the financial windfall doesn't do much for your life, then you will likely feel a great let down because doing something mainly for money tends to feel empty.

My thoughts:

The money received from selling Financial Samurai won't change our lives. The only thing I might do is buy a bigger house. But I've already done the analysis on a larger house before, and it doesn't feel worth it. Instead of feeling joy, I feel my headaches of owning a larger property with a $55,000 annual property tax bill would only multiply.

With the windfall, I'd give more money to a foster youth organization I volunteer at. I'd pay for a luxurious cruise for my parents. If my parents wanted, I'd also pay for their home remodel while putting them up in a nice temporary housing condo in Honolulu.

Other than these things, there's really nothing more I'd do with the money except investing it in passive income generating investments. When you are already free to do whatever you want, having more money doesn't move the happiness needle much.

6) Will you regret not selling your business if the market turns south

Fantastic selling opportunities open up only so often. If you pass on selling your business, can you live with your decision that you could have gotten so much more if you sold earlier?

Do you have the patience to wait for another 10 years for the next fantastic selling opportunity?

For example, Yahoo was once once worth over $100 billion and eventually sold itself to Verizon for only $5 billion. The good times don't last forever.

My thoughts:

I'm sure I'll regret not selling today if I could only get 95% less years later. Meanwhile, however, I will have gotten a priceless amount of joy building Financial Samurai. It's cool to have a web property I can click on from anywhere in the world.

It's the same type of pride and joy you get as a parent when you look at your kid and think proudly, I helped make that. If you truly love your kid, you would never sell him or her. The same goes with your business, sometimes to your detriment.

I also am pleased with the steady growth of the Financial Samurai Forum. It feels like a new website with different offerings I will help nurture. I'm sure it will grow into a tremendous destination if I can manage it well over the next five years.

7) Will the new buyer be a good steward

You don't want to sell your business to anybody. Instead, you want to sell your business to someone who believes in your vision and carries out many of the things you'd like to do, but don't have the ability or energy to do on your own.

Consider selling your business similar to giving away your daughter or son's hand in marriage. You're definitely not going to let your daughter or son marry a scumbag.

My thoughts:

After several conversations, I finally warmed up to someone who I think could really grow Financial Samurai and improve the user experience. Like me, he is a father, but to three boys. He has a team of hundreds of writers and developers who could create a lot more value. Let's see where this relationship takes us in the future. I'm definitely going to take my time finding a proper suitor. 

Enjoy Your Business For As Long As Possible

Things to consider before selling your business (baby)

The joy you get from creating something out of nothing far outweighs any joy you get from making a lot of money.

Yes, there will be difficult times when you'll just want to sell and quit. Do your best to keep on going.

I know of several people who sold their online businesses for the money and later became depressed because they didn't have a purpose anymore. Many in the online media space tried to re-create the magic and failed. They became irrelevant.

Don't Rush Into Selling Your Business

Money really doesn't bring much more happiness once you're earning enough to have all your basic needs met. Some say that number is $75,000 a year, while others believe $300,000 a year is more likely in a HCOL area.

If you feel the end is near for your business, definitely try and sell. If someone gives you a crazy offer way outside average valuation multiples and you're burned out, then accept their offer with open arms.

But if you continue to enjoy what you do and see growth potential, then keep on going. It's probably not the ideal time to proceed with selling your business. After all, the legacy you leave will be wonderful. Just remember to always keep an open mind as there is a price for everything.

Not a day goes by where I'm not thankful for launching this site in 2009. It has given me more joy and purpose that I ever thought possible. Thank you!

Suggestions For Business Owners

There are two suggestions I tell everyone who wants to launch their own business and those who are just starting to grow. 1) Make sure you have an online presence and start your own website. And 2) take advantage of all the benefits of a business rewards credit card. Here's why.

Start your own website

Hand down, every business needs its own website. Here's a step-by-step tutorial that shows you how to make one. Your customers expect an online presence and won't trust your business as much without one.

Not a day goes by where I'm not thankful for starting Financial Samurai in 2009. I ever would have imagined being able to engineer my layoff from a well-paying job in 2012 to just write and be absolutely free.

You just never know what might happen if you try. Back when I started, I had to hire someone for $1,500 to launch FS. Now you can launch your own website in under 30 minutes for less than $50.

In addition, if you enjoyed this article and want to get more personal finance insights and tips, please sign up for the free Financial Samurai newsletter. You’ll get access to exclusive content only available to subscribers.

Venture Capital Investing

Instead of selling your business, invest in private businesses. Venture capital investing is an area predominantly dominated by the rich. Investing in private companies is where you might be able to find the next Google, Meta, Figma, Apple and more. Personally, I allocate about 10% of my capital to venture capital.

The most interesting fund I'm allocating new capital toward is the Innovation Fund. The Innovation fund invests in:

  • Artificial Intelligence & Machine Learning
  • Modern Data Infrastructure
  • Development Operations (DevOps)
  • Financial Technology (FinTech)
  • Real Estate & Property Technology (PropTech)

Roughly 35% of the Innovation Fund is invested in artificial intelligence, which I'm extremely bullish about. I don't want my kids asking me in 20 years why I didn't invest in AI or work in AI today. 

The fund's investment minimum is also only $10, as Fundrise has democratized access to venture capital as well. Most venture capital funds have a $200,000+ minimum. 

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33 thoughts on “Things To Consider Before Selling Your Business (Baby)”

  1. I used to imagine selling my business before I turned 40, but things just didn’t work out that way. And I’m actually quite relieved. I love the autonomy I have being my own boss and working on what I want to work on, and not having to bow down to a boss or needy investors. I don’t think I’ll ever get super crazy rich, but I have more than enough to live a very comfortable life and provide for my family. Sure I believe there’s a price for everything, but for now I’m happily designing away and enjoying all the flexibility I need.

  2. Angela Waterford

    My sister told me that there will come a time that I may need to sell my future business if my pastry shop becomes a failure. You’re right about saying that I should look at my future business and see if it has a lower valuation so that it will sell at a good price. I think I might need the help of a broker in that situation because I’m not familiar with the process of selling a business.

  3. Adrian Doyle

    Sam – I’m curious: you mentioned that you expect interest rates (and therefore presumably inflation) to stay low for the rest of your lifetime.

    Why do you think that to be the case?

  4. Financial Chipmunk

    Great article. A lot of informative stuff! Interesting to hear your thoughts on FS and the business side of things. A lot for me to learn from this! Starting a blog is so easy but it’s a skill that’s difficult to master. FS proves that you’ve mastered it.

    All the best in finding a good buyer. From what I read you’ve already made up your mind to sell? It all depends on the right buyer and price..

    Best of luck. FC

  5. Given the valuation levels, limited reinvestment opportunities with a similar cash yield and the fact that you love writing, I simply struggle to see how selling FS would make sense for you.

    I also suspect it will be hard for any acquirer to offer you true intrinsic value for FS given the inherent information assymetry. A lot of the value in FS is linked to you and your authentic writing style – if I was the buyer I would want serious assurances that you would continue being involved in a significant capacity… but if you continue being involved, what’s the point of selling? You end up becoming an employee again.

    Even if you were to have a significant cash requirement, you would probably be better off levering up FS (at a conservative level) as opposed to selling it together. The business is now probably suffiiciently scaled and you would also get the benefit of the tax shield while paying yourself a tax-free dividend.

    1. What people don’t realize is that the comments and traffic from each new post is only a tiny percentage of overall traffic and revenue.

      Most traffic is new traffic from search engines.

      But in general, I agree. Investing in your business often has a much higher return than anything else.

  6. I started a website back in college. It covered a fad before it became main stream. Consequently, the website received a lot of hits. I also started a message board on the site for the community members and there was a lot of participation as well. The website was grossing over $30,000 a year then with little effort to monetize the traffic.

    Unfortunately, I wasn’t focused on growing the site beyond the fad and it ultimately died when the fad faded. I also received some low ball offers for the site which I turned down. In hindsight, I should have done a lot more to (1) grow the website traffic by branching out to other related topics, (2) start an associated retail business, and (3) create an associated lifestyle company.

    But I lacked the creativity and imagination to see all this back then. Who knows where it might end up if I was smarter back then with the website.

  7. I started an online tax practice in 2013 and sold it late last year. I received 2x gross revenue when no firms were getting more than 1 to 1.25 gross max. I was feeling burnt out and I honestly never had any emotional attachment to the business. It was never “my baby”. I enjoyed working with my clients but I realized what I liked most was growing a new business. So I took the offer and got him to allow me to grow a new accounting and tax practice that targeted a different market. I don’t regret it one bit so far.

    For me I always felt there was a bigger risk of the market collapsing and the business losing significant value than me selling too early and missing out on further growth. I was at a point where I either needed to start hiring employees or sell. Additionally the offer was a 100 percent cash up front offer with no contingencies on client retention. It was a deal I couldn’t refuse.

    The money didn’t set me up to never work again, but in my very LCOL area it sure went a long way and allowed me to invest even more in real estate. My days are far less stressful now. For whatever the reason I never hesitated with this decision or felt any resistance.

    Definitely a lot to weigh with the decision to sell a business.

    1. Congrats! Given you got a value 70% higher than the maximum average, you should feel pretty good given everything is relative.

      How did you reinvest the proceeds? And how do you feel not having as much or any income coming in anymore?

      Although I have retirement income, I just wonder how I’ll feel if I no longer have active income coming in, since I’ve basically had active income for 20 years + my time in college and high school.

      1. I used the proceeds to pay off all non-mortgage debt, max out all available retirement accounts for my wife and I for a few years and invest more in real estate. I own 16 investment units now and have done a few flips so it’s growing quickly.

        It was definitely a little worrisome to go from $20k-$30k a month in income to much less, but the new accounting business I cofounded is already bringing in good revenue, the real estate is cash flowing well and the new owner of the business I sold pays me commissions for bringing in new clients. So there’s still at least $10k coming in most months, and as high as $37k last month (though a lot of that was one time payments and abnormally high). The uncertainty is scary at times, but I enjoy life much more these days.

        One other thing I would add about owning a business vs being an employee that you touched on a bit but is so powerful… every dollar you earn in a business multiplies your net worth by much more than just that dollar. When you are paid a dollar as an employee, your net worth increased by a dollar (ignoring taxes, etc). When you earn a dollar in your business, your net worth increases by two, or three, or six or 12 or more dollars depending on the multiple of your industry, because you are increasing the market value of the business itself. Earning money in a business is truly like steroids for your net worth.

        1. Good stuff Josh. Good you have alternative income streams already in place. Sounds a little like you’r still working for the business as a salesman no? It’s a good arrangement for the new buyer.

          May I ask why you sold the business given you decided to start a new business that sounds exactly the same? Was it simply to lock in profits and reduce risk?

          Many people in the online media business have cashed out over the 10 years I’ve been around. But only one that I know of has been able to come close to replicating their success.

          Good point on business income vs. salary income in growing net worth. Love that multiple!

          1. For the old business I mostly just go on business podcasts, give tax tips for their audience, and then the new owner pays me a 50 percent commission for any revenue that comes from that. It’s a nice way to get paid for something I enjoy doing (and something that grows my personal brand).

            Good question on why I would sell and then start a new business that sounds the same. First, it was an amazing opportunity. I partnered with a guy I used to work at a CPA firm with who is phenomenal at doing the work. So him and our only employee handle all the day to day work and I only focus on the sales side, which is where my skill set is best used and what I enjoy the most. It’s actually growing incredibly quickly and will likely pass the business I sold in gross revenue by year end. It’s also a different model where we only focus on high dollar clients for high end services. So a lot less clients to manage to get to that revenue. Basically it was just a way to leverage the personal brand I had built into a new venture that requires much, much less of my time.

  8. No business would buy an affiliate only business for 12X, just not going to happen unless you were the size of Student Loan Hero, or you really monetize poorly. I argue Lending Tree overpaid for Student Loan Hero. It’s too much risk for 12X for a company to bare.

    If I were in your shoes, I would find ways to better monetize.

    1. Didn’t know about SLH. $60 million sounds good to me, especially given it’s a similar size to FS. Wouldn’t it be a no brainer to just create some random tools just like that site?

      I just don’t think selling anything for less than 8-10X times operating profit makes sense if your business is growing double digits each year. In finance, we would often value a company on a multiple closer to its growth rate Eg 20% grower = 20X multiple.

      I feel like I haven’t even gotten started yet if I’m trying to make money. I just don’t know what more money would do for my life.

      It might be a fun and good challenge to try to make lots of money.

      I’m happy you cashed out. Just don’t think the timing is right for me.

      1. “I just don’t think selling anything for less than 8-10X times operating profit makes sense if your business is growing double digits each year.”

        If you are affiliate only there is an upper limit of how much growth you can achieve. I believe I hit the growth limit.

        I realized my site would have to be much different (which was the plan) but why not lock in the gains from the existing site? Which is exactly what I did.

        My non-compete ends July 2020, look me up if you still own this site as there are many things that can be done.

  9. Selling a business can be a personal thing as well and I like your point about finding a good steward. This is good advice when buying a business as well that 2nd or third highest offers often get accepted if the selling owner resonates with the direction that you communicate taking this business in. After all she may have spent maybe decades building it. Right?

    1. It’s the same thing with selling a property. If you can find a buyer you can connect with and you know will take care of the property, you’re more inclined to sell to them in a competitive market. Hence the goal of buyers to create that good steward connection.

  10. I sold the service business I started in 2011 via an ESOP in 2017. It had grown from 1 employee to more than 20 in that time and I realized I had had enough. I do not regret selling at all despite the future income hit. Trying to manage people isn’t enjoyable, but it facilitated the growth necessary to quasi-retire early. Your business potential is correlated to the time invested on some type of non-linear curve and I presume requires modest management of people. Sounds like an awesome place to be. When you extrapolate your growth you probably see exponential returns on your investment. Most business owners probably see more of a linear relationship between time and money.

    1. Congrats on selling! Yes, I have no desire to manage full-time employees. It’s just my wife and I keeping things going. We can hire freelancers to get 100% of our work done and outsource everything if we wished.

      I don’t know about the non-linear growth curve. But maybe, given the internet is infinitely scaleable at my size (small).

      What do you do for active income now?

  11. It is apparent that if you do something for the love of money and the desire for more money, your business is likely not going to grow as fast as I could or be as successful as it could.

    Every single personal Financial Blogger who sold, sold too soon and did it for the money and not because of their joy of writing.

    And almost every single one except for one has failed to create a successful new personal finance side to make more money.

    Isn’t it funny how the less you focus on money the more money you can make?

    1. So if all but 1 of the businesses failed after the sale, didn’t the bloggers sell at the perfect time? The fact that most fail is what puzzles me on who is actually buying sole proprietor content generating websites. It would take a very unique and capable buyer to make it make sense to pay the kind of multiples being discussed, but admittedly this is definitely not my area of expertise. Maybe there are tons of success stories. My experience has been small companies are exponentially harder to sell than large ones. I’m with Sam, that unless he gets a ridiculous offer (which he probably already has) he shouldn’t sell. They would have to hire 3 writers to come up with 50% of the quality of content he can do in a few hours a week.

  12. Excellent job growing Financial Samurai over the last decade. It was a lot of work.
    I had several lowball offers throughout the years for my site. Usually, it’s around 2x revenue. That’s not worth it especially since I still enjoy blogging. If I’m burnt out, I’d probably sell.
    I might sell for 6x, though. That’s much closer to the date I’m planning to stop blogging (or slow way down.)

  13. Hi Sam, thanks for your deeper insights on the matter.

    It is great that you mentioned the regret issue. I also see that regret might be one of the relevant points while deciding to sell a business. The right valuation is essential of course. But even when selling at the “right price”… regret might show up sometime after the sale.

    Not an easy decision to make… I wish you all the best!

    1. Thanks. Yes, once you reach the payback period, all the time after that period is full of regret for many entrepreneurs. “Why did I sell!?” “Why didn’t I just keep on going?!” That continued success could have been yours! etc.

  14. After reading this post it sounds like there is still a chance you may continue to own it and potentially pass it down as a legacy, which if you polled your readers I think everyone would prefer that.

    Of course we can not blame you if you do sell for an amount that is too hard to pass up.

    I enjoy writing and creating and it is a great experience to have people visit my site and comment on it. Of course my site is exponentially smaller than yours but it also is just a year old and I agree that it takes time to build something that gains traction.

    Appreciate you sharing your thought process on the whole situation.

  15. Dave @ Accidental FIRE

    That’s good insight, and there’s lots to consider. You’ve been at this game so long I couldn’t imagine what it’d be like to consider selling.

    If I keep at it for another 8 years maybe I’ll have these problems one day ;)

  16. Hey Sam, I’m glad to see you’re leaning towards keeping FS alive and well! That’s of course for selfish reasons, but it’s also great to know you’re still able to find joy in your successful passion project.

    I’ve definitely thought about how life might have been different had I not sold my business several years ago. But, in any scenario, I can’t imagine how earning more money would be better than being 100% present with my family these past few years.

    I think you’ve got the best of both worlds at your fingertips. I’m sure you have moments of frustration like any business owner, and given your operating margins, perhaps you should consider offloading more of the mundane tasks so you can simply concentrate on the parts that give you the most joy.

    Best wishes for the next decade of FS!!

    1. Good to hear you did not regret selling Michael.

      You make me think, if I can have the best of both worlds by owning a business that still provides mostly joy while also being mostly present for my family, then I should continue until I no longer can.


  17. So many helpful and wise things to think about for those looking to sell! It’s very impressive you are approaching your 10 year anniversary and that you’ve maintained such a high level of quality content and consistency in publication. That is something to be incredibly proud of and a wonderful gift to potentially pass down as your legacy to son. You’re an inspiration to us all!

  18. Jonathan @ Mr. Centsible

    Thanks for providing such personal insight and commentary for your website. It’s definitely one of the unique characteristics of your site.

  19. This post makes me very happy. I’m glad to hear you’re in this headspace right now. Be proud of what you made, and for how you inspire others to join you in finding their voice and a possible route to financial well-being. Thank you.

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