Reflections On Making Money Online Since 2009

Financial Samurai has technically been making money online since it started in July 2009. I think the site made $3 the second month the site was live. Whoo-hoo! Although I didn't focus on making money online, the site began to generate revenue as it grew anyway. Do something you love and the money will follow right?

By the time 2012 rolled around, I figured with the combination of my passive investment income (~$80,000) and online revenue I'd be fine if I took a leap of faith. Besides, my wife promised to keep working for 2-3 more years until she turned 35 as well.

If you're looking to make money online, become an entrepreneur, or grow your business, let me share some important lessons I've learned along the way. These points are salient for anybody looking to grow their career as well.

The Gradual Shift Towards Entrepreneurship

From 2012 to the end of 2017, I decided to become more entrepreneurial. I changed my time split from 90% fun / 10% business to 80% fun / 20% business. The last thing I wanted to do was make Financial Samurai feel like a job when a job is what I had escaped.

But about a year after our son was born in 2017, I dialed up the business percentage to about 30%. Our monthly health insurance premium was rising to $2,000 and we had to plan for $1,950/month in preschool costs in 2-3 years. As someone who likes to plan ahead, I now had a purpose to make more money.

Once our daughter was born in late-2019 and the pandemic hit in early-2020, I decided to crank up the business percentage to 40%. I figured, if I was going to be trapped at home more often, I might as well make more money online. Larger family, larger costs.

Now that the pandemic is over, I've decided to dial back the business percentage to 25%. After all, 25% was my happy state. And I want to be as happy as possible during the YOLO Economy. The time to live free and relax is now!

Spending 15-20 hours a week writing, communicating, and negotiating is the sweet spot. Just enough time to stimulate the brain and plenty of time left for family and leisure. Find your ideal sweet spot and work like hell to achieve it.

Things To Know About Making Money Online

Hopefully, all of you have decided to figure out ways to make supplemental income from home after the lockdowns. Having an online business that can't be shut down is extremely valuable, especially during the next black swan event.

If you want to make money online, let me share some thoughts I've learned since 2009.

1) Consistency Matters Most

In order to make money online, you must stay consistent with your product. Nobody wants to listen to or buy something from a business that is new or inconsistent. Your clients want to know you're going to be around tomorrow, the next week, the next month, and the next five years.

Think about life insurance companies. Would you buy a life insurance policy from an upstart? Or would you rather buy life insurance from a company that has been around longer than you? It's important to believe the life insurance company will outlive you. Otherwise, your beneficiaries might not get paid out.

Doing something consistently for one year is the absolute minimum if you want to make money online. Once you produce a product consistently for 36 months in a row, I'm confident good things will happen. And if you can stay consistent for 10+-years in a row, business success is all but an inevitability.

When you come to Financial Samurai, you know that if you subscribe to my post e-mails and newsletter, you will be able to read something insightful for free at least a couple of times a week. You will gain different perspectives from someone who has written about personal finance since the last global financial crisis.

If you're losing momentum, tell yourself this: Why quit when you can keep on going?

2) Build A Brand

Why does Rolex get to charge $10,000 for a Milgauss GV watch that requires $1,100 in maintenance every five years when a similar, maintenance-free watch from Casio can only charge $500? Why does Hermés get to charge $200 for a silk-tie when you can get a similar-looking tie for $10 at Ross?

A strong brand is what enables you to stand out from a crowded field. A great brand is what enables you to charge premium prices. A business with a strong brand tends to gain a disproportionate amount of opportunities.

For many solopreneurs starting out online, their brand may be themselves. Over time, they craft their brand based on their evolving vision. You need to spend time figuring out what your business stands for and then spend the effort to build your brand. Make sure you stand for something!

The Financial Samurai Brand

Reflections on making money online since 2009

Financial Samurai is an independently-owned personal finance site that helps readers slice through money's mysteries. Because money is too important to be left up to pontification, everything written here is based on firsthand experience. When you come to Financial Samurai, you will read insightful information to help you make more optimal financial decisions.

The online media world is interesting. You either want to hire a bunch of freelance writers to produce a lot of content to attract a lot of traffic quickly. Or, you can go my route and slowly write almost everything on your own.

Personally, I want to read articles by people with the most expertise and experience. A journalist or a freelance writer is an expert in writing and reporting, not necessarily on the subject matter. It’s up to you who you want to read.

I decided not to go the freelance writer route because I thought it would dilute the Financial Samurai brand in the beginning. For the first 10 years, I wanted to build Financial Samurai into a respected personal finance site written by someone with a finance background.

It was important to prove out my concepts and live my beliefs. Only after 10 years, would I consider hiring freelance writers that embodied the brand and take a step back.

Boosting The Brand With An Instant Bestseller

Today, I've got a new Wall Street Journal bestselling personal finance book with Portfolio Penguin entitled, Buy This, Not That: How To Spend Your Way To Wealth And Freedom. The book further legitimizes the Financial Samurai brand and reaches an even wider audience around the world.

You can click the image to pick up a copy from Amazon. The book is your unfair advantage to building more wealth and making more optimal decisions.

Buy This, Not That: How To Spend Your Way To Wealth And Freedom Bestseller

3) Decide On A Lifestyle Business Or Something Bigger

You must decide whether you want to build a lifestyle business or build something potentially much larger. If you can hire, inspire, and manage the right people, you could make a lot more money online. Just know you might not be happier.

When I first started, I decided I'd rather have a lifestyle business that made a comfortable amount of money than a big business. The blue sky scenario I presented to my poker buddies at the table was this: Make $200,000 a year working 15-20 hours a week on something you enjoy with nobody to report to OR work 80 hours a week for 5 years for a 25% chance of a $25 million payout.

I decided to go alone because I don't enjoy managing people. Further, I had enough passive income to cover my basic living expenses. An additional $50,000, let alone $200,000 in online income was more than enough to live well. When my wife finally negotiated a severance in 2015, I was no longer alone. I had her, which was perfect.

Until this day, it's fun to do some brainstorming with my wife for 30 minutes a day. It reminds me of when we'd study in the library together as college students. Having someone to keep you company is lovely.

She helps write on occasion and spends most of her time working on vital back-end tasks. We've also learned to focus on our strengths and utilize the concept of separation of tasks. To not have to deal with office politics and HR issues is also lovely.

4) You Don't Need To Be An Expert Or Have The Best Product

One of the biggest fallacies in making money online is thinking you need to be an expert in your field or have the best product. I thought this way until 2017 when I started observing other online businesses with fewer credentials than I thought was necessary, do very well.

Here are real examples that prove being an expert doesn't matter:

  • A guy with a pool and hot tub cleaning site who has never owned a pool or hot tub: $400K+ a year
  • An accountant with a plumbing and HVAC lead-generation site that has no plumbing or HVAC experience: $100K+ a year
  • A gal who started a site on how to make money online when she wasn't making any money online: $1M+ a year
  • A TikTokker in high school teaching his followers about investing in meme stocks with his $500 portfolio: $100K a year
  • A 26-year recent college graduate writing a bestselling book on how to be rich and find the meaning of life

Making money online is not like having to go to medical school for four years and then residency for three years before you can perform heart surgery.

Literally anybody who knows how to type can start a website and earn money. You just need to start and learn the fundamentals of online traffic acquisition. Over time, you will naturally learn by doing. And the more you do, the more you will become an expert.

You Can Hack The System

Google likes to go on and on about the importance of Expertise, Authority, and Trust (EAT) to rank well in search. But based on my observations over the years, EAT matters much less than you think. Google simply cannot properly measure a site's EAT.

One of the reasons why site owners are able to hire a bunch of freelance writers and grow traffic tremendously is because EAT doesn't really matter. If EAT matters, why are there literally millions of sites with no expertise that still do well in search? We've all stumbled across spammy sites and have wondered, wtf is this?

Google uses impersonal algorithms like content length, keyword count, and site speed to determine search rankings. There is an entire Search Engine Optimization (SEO) industry out there looking to game the system to help websites rank better. For example, SEMRush is a publicly traded SEO company worth ~$2.4 billion.

Example Of Getting Screwed

Unfortunately, writing good content or being original is not enough. I'll give you an example of how hacking the system can trump good or original writing.

A while ago, I came up with the 30/30/3 rule for home buying. However, if you Google “30/30/3 rule” my original article won't appear. A guest post I wrote on CNBC shows up. But other than that, random websites that give me no credit show up on page one. Google is not smart enough to even rank the original.

In fact, every time I publish a post, a half-dozen sites literally scrape my entire post and republish it on their websites. Usually, their posts won’t rank. But sometimes they do. The system is imperfect, which is partly why the SEO industry exists.

If you really want to make money online, don't be like me and let pride and honor get in the way. There are plenty of people getting rich online relatively quickly by taking shortcuts. But if you want to feel good about the way you grow your business, you might want to go the slow and steady route.

Related: Accept That You Will Always Get Screwed And Move On

5) Focus On What You Enjoy And Have A Mission

Given one of the keys to making money online is staying consistent, starting a business you enjoy will help you keep going. In addition, your business must have a positive mission. There is no way I would spend 10 hours writing and editing this 4,100-word post if I didn't love to write.

One of my favorite mission-oriented businesses is TOMS shoes. For every pair of TOMS shoes purchased, a pair of new shoes is given to a child in need in partnership with humanitarian organizations. With such a mission, how can you not be motivated to grow your business?

Financial Samurai's mission is to help everyone achieve financial freedom sooner, rather than later. The longer I've been away from a job, the more motivated I am to help people build more wealth.

The freedom of not being beholden to anybody is priceless. I want everybody to have enough money to stand up for themselves and for others and not fear devastation.

Every time someone sends me an e-mail or leaves a comment that some article I wrote helped them, I immediately get a power-up for another week. Helping people is addicting.

I love how nobody has to pay anything to read anything on this site. Ironically, the more value you can add for free online, the more money you can make online. Bloggers make a lot more than people think.

Access To Good Financial Education For All

I keep thinking about the kid on a computer at the library because she can't afford a computer and internet at home. Or Daniel Cabrera, the homeless boy in the Philippines doing his homework outside of a McDonald's for its light.

Daniel's father died when he was six and their shanty home burned down when he was four. Yet Daniel keeps on fighting! Daniel said he wants to be a police officer when he grows up.

Putting up a paywall will never happen on Financial Samurai. If I did, that would mean I was putting making money online first over writing personal finance content to help people.

If people want to support Financial Samurai pick up a hard copy of my affordable book, Buy This, Not That and leave a review on Amazon. I'll get around 12% from each book sale, and then I'll donate it to charity.

Or you can buy a copy of How To Engineer Your Layoff, if you want to learn how to negotiate a severance package and break free from a job you dislike. Negotiating a severance in 2012 at age 34 was my #1 catalyst to change my life for the better.

Daniel Cabrera - Filipino kid doing homework outside McDonald's

6) Choose A Profitable Niche

Not all niches are created equal. Some are much more profitable than others. Here are some of the more profitable niches online in no particular order.

  1. Fitness and Weight Loss
  2. Mental Health
  3. Dating and Relationships
  4. Pets
  5. Self-Improvement
  6. Personal Finance
  7. Making Money Online
  8. Beauty Treatments
  9. Gadgets And Technology
  10. Food

Everybody wants to look good, feel good, have more money, find love, and be happier. Therefore, focus on a niche that provides these things and solves common problems. At the same time, focus on a niche where you also have interest and some expertise. The more interest and expertise you have, the easier it is to last.

I just so happened to focus on the personal finance niche because I wanted more money to have more freedom. I worked in finance for 13 years, went to business school, and invested in multiple asset classes for passive income. Therefore, writing about personal finance topics came naturally. I simply had to write about experiences. As it turns out, lots of people want the same thing!

If I had written about pets, I would have failed in under a year. I'm allergic to cats, don't have a dog, and am not interested in getting a turtle. Therefore, I wouldn't be able to generate enough traffic to sell enough pet food, pet toys, pet training books, etc.

Instead, I'd have to hire freelance writers to create a false reality that my website was the go-to source for pets. And the reality is, I could probably do it and make decent money online. But this path just wouldn't feel right.

Related: Discovering Who Makes $1 Million A Year (Top 0.1% Income)

7) Your Income Potential Is Unlimited

If high schoolers knew how much money they could make online, I'm not sure they'd spend four years and all that tuition going to college anymore. If colleges knew how much people could make online, they'd all offer courses on online entrepreneurship.

Job income upside generally pails in comparison to online income upside. With over 3 billion people online and growing, an online business owner has infinite scale. Meanwhile, a typical person with a day job always tends to face some type of ceiling. The ceiling might be a manager who won't let you ascend until she ascends. Or, the ceiling might simply be due to what you look like.

With online entrepreneurship, it is easier to decide how much you want to make and figure out various ways to get there. With a day job, you can rarely ever make more than your immediate boss. In a way, online entrepreneurship is like going straight to the corner office.

8) Decide Your Ideal Passive And Active Online Income Split

There are some people who have created niche sites that make money passively without doing any work after the initial setup. For example, one guy makes between $500 – $1,000 a month selling hunting knives. However, over time, more focused competitors tend to take over. Further, Google algorithms often change as well. Therefore, you always need to do some updating to your business to stay relevant.

Programmatic advertising income is considered passive once you've set up an ad network like Google Adsense or Adthrive. For example, I can write about a new pair of tennis shoes I bought. If I do, customized ads showing the latest Nike tennis shoes may start appearing on my site. If someone clicks on the ad or views it, I get paid.

Or I can write nothing and just let traffic come to Financial Samurai from the search engines on various topics. Advertising will be displayed automatically based on the type of article.

Finding business partnerships is considered active income. Companies hire MBA graduates for Business Development roles all the time. It requires product understanding, negotiation skills, selling skills, and lots of hustle.

For example, I could start contacting all the top financial planning companies to see if they want to partner with Financial Samurai. If one was interested, then I'd have to come up with a partnership agreement that contains all the terms. Then I'd have to execute the agreement, fill out invoices, and stay on top of my accounts receivable. It can be a lot of work.

Discovering Big Demand

Given I want to run a lifestyle business, my ideal passive/active online income split is about 80/20. But during the height of the pandemic, I decided to flip the percentages around and search for or solidify existing partnerships.

What I found was that the demand to partner with Financial Samurai was much bigger than I had expected. I had underestimated the strength of the Financial Samurai brand. For so many years, I throttled my own money-making opportunities because I focused predominantly on fun. If I didn't have fun, I wouldn't want to write. But because I had fun, I kept going and the site naturally made more money. A little ironic right?

Business development can be enjoyable. It's satisfying to negotiate and close a deal. However, everything has its limit. When I opened the doors to new partnerships in 2020, I was overwhelmed. It no longer became enjoyable trying to negotiate deals with so many potential partners. And as the economy opens up, there is huge pent-up demand to advertise even more.

Instead of going after all opportunities, I'm self-throttling again for my own happiness. I also don’t want to write for the search engines. Be OK with leaving money on the table. Given there is an endless amount of money to make online, you need to set a limit for how much is enough.

9) Build Your Own Moat To Protect Your Business

If you are serious about making money online, you've got to build as many diversified revenue sources as possible. This way, if one revenue source goes down, your other revenue sources will keep you afloat.

Reflections on making money online since 2009

Being too dependent on Google is no good. You could easily be demoted in the search engine rankings one day without reason. Therefore, you must build a newsletter where you have full control over what gets sent to your most avid customers.

Being too dependent on one business partnership is no good either. The business partner could go out of business, cut its budget, or change its business. Therefore, you probably want to have at least two or three business partners per vertical. At the same time, you want to bet more on the winning business partner. Therefore, keep close tabs on how your business partners are doing.

The way to not be dependent on other businesses for revenue is to create your own product. Mostly due to laziness, I've only created one product since 2009. That product is my severance negotiation book. At least my wife and I have updated the book five times and expanded it to the best book there is on the topic.

If I were to start over, I'd focus on building the free Financial Samurai newsletter from day one. I'd also create a new product every two or three years. It was just hard to do that because I didn't start Financial Samurai as a business. I started the site as an outlet to deal with fear and uncertainty during the financial crisis.

But for those of you who are focused on making money online, you must own your distribution channel so you can better control your destiny. I find tremendous comfort I knowing that no matter what the Google algorithms do, I will always have a newsletter with over 60,000 active subscribers.

In addition, I've been building the Financial Samurai podcast (Apple, Spotify) more consistently starting in 2021. Today, the podcast has over 200 episodes and over 400 reviews. It's another way to build a brand and have a direct relationship with my readers and listeners.

10) Come Up With Clear Reasons Why You're Working

Here is an interesting phenomena that happened to me in 2020. The more I made through active income the unhappier I got. That forgotten feeling of emptiness I experienced while in banking started growing inside again. I began wondering what the hell was the point of it all? Trading more precious time for more money that made less of a difference felt bad.

To counteract this negative feeling, I made concrete financial goals for why I was spending more time making more money online. I needed a clear purpose for spending time beyond my comfortable 20-hours a week cadence. The reasons included paying for the following:

  • $2,500 a month in unsubsidized family healthcare
  • $4,000 – $6,000 a month in preschool and grade school tuition
  • $1 million for college for two kids in 14-17 years
  • Providing an educational opportunity about online media for my kids

Once I created clear reasons for making more money online, it became easier to grind away. Purpose matters! Ultimately, my goal is to invest online income to create more perpetual passive income.

But the reality is, I've been tricking myself during the entire pandemic. These expenses have already been covered by existing passive income. Therefore, I told myself after I bought my “forever home” in 2020 that I needed to build more wealth to pay off the new mortgage. The cycle never ends until you decide to end it.

11) Decide How Much Is Enough

Because your online income potential is unlimited, you might find yourself never feeling like you're making enough. You look at other people with bigger teams, more traffic, more accolades, more revenue, and feel like you should do more. It's like investing FOMO, but for business.

This “never enough” feeling is one of the biggest downsides of trying to make money online. At least with a job, you know that your salary is capped no matter how much you work. Therefore, you feel OK slacking off on occasion. Being able to take paid vacation days off, go out for long lunches, and take paid parental leave for months is awesome! No matter how much you take it easier, so long as you don't get fired, your day job salary won't change.

The correlation with effort and reward tends to be much higher with online entrepreneurship. There is always something more you can do. Therefore, it is imperative you decide how much money is enough for you to be happy. If you do not stick with this amount, you will eventually become miserable.

It took me 13 years to find my enough to retire from traditional work in 2012 with just my wife and me. Walking away from a $250,000 base salary was not easy at age 34. But it had to be done for my soul.

It has now taken me five years to find my enough online to take things down again with a family. This time, walking away from money is not as hard even though more is at stake. The bull market is a big reason why. But it’s really the kids. Having kids accelerates time because they change so quickly. I don’t want to miss too many more moments.

Related: How Much You Need To Make As An Entrepreneur To Replace Your Day Job Income

12) Be Realistic, Not Delusional

Too many people confuse their success due to their skills rather than due to their company's brand and platform. For example, no institutional client called me because of me when I was 24 years old. They called me because I worked for Goldman Sachs. As a result, it wasn't until after 10 years of experience did I consider joining a smaller shop for potentially more upside.

If you join The New York Times and start believing you're the reason why you suddenly have millions of readers, you are fooling yourself. At the same time, joining a reputable company is the easiest way to gain immediate credibility without having to go through the slog of building something on your own.

If you truly believe in yourself, then you should be an entrepreneur. But I suggest learning as much as possible with an employer first. Don't let delusion take over your life!

13) Appreciate Your Wins

As an entrepreneur, you will experience the highest highs and the lowest lows. We call this the trough of sorrow. The emotion is more intense because your business is your baby. Everything depends on you. It's more personal too.

Therefore, I suggest moonlighting on your business while having a day job first. Only after you see your side business gain some traction should you take a leap of faith.

As an entrepreneur, it's often easy to dwell on the losses. A competitor might have copied your product. Google might have hit your organic search traffic. A client might have closed down and decided not to pay your last invoice. These losses take away motivation to keep going. Don't let it.

During bad times, be grateful for your wins and good fortune. Recognize how far you've come. It's easy to get spoiled by any success you may have. Hedonic adaptation can be a real downer sometimes. Just the fact that you tried to run a business is more than 97% of people who don't. As long as you are trying your best, you will likely never regret the outcome.

Even if Financial Samurai loses all its traffic tomorrow, I'm thankful for everything that has transpired since 2009. The site has grown far beyond what we could have imagined.

Making Money Online Is The Future

Just like investing in real estate in the heartland of America is the future, so is making money online. The key to building above-average wealth is to recognize long-term trends and allocate your energy and resources accordingly.

I'm excited to be a father because I can't wait to teach my children everything I know about online entrepreneurship. The ability to generate online revenue is one of the main reasons why I'm not stressing about them getting into a good college or land a good job. There are no longer any gatekeepers!

Thanks for letting me reflect on my online journey since 2009. I hope some of my thoughts can help you grow your business or career. If you can create a product you feel good about every day, I dare say you have a winner! And being able to utilize your creativity to grow your business is a priceless experience.

I'm looking forward to taking a nice sabbatical after California fully opens up on June 15. Further, I'm ruminating over what to do for the next 10 years. I can't remember being this excited about taking a long vacation!

Start Your Own Website Today

If you'd like to start your own site, you can follow my step-by-step tutorial here. When I started in 2009, I had to hire someone and pay him $1,000 to start. Now, you can do so yourself for less than $50 and complete the task much quicker.

Just know there are plenty of people making a lot of money online who don't have the relevant background in their field. Don't think you need to be an expert with experience to make money online. It's still the wild-wild west!

Invest In Private Growth Companies

In addition, consider investing in private growth companies through an open venture capital fund. Companies are staying private for longer, as a result, more gains are accruing to private company investors. Finding the next Google or Apple before going public can be a life-changing investment. 

Check out the Innovation Fund, which invests in the following five sectors:

  • 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. In 20 years, I don't want my kids wondering why I didn't invest in AI or work in AI!

The investment minimum is also only $10. Most venture capital funds have a $250,000+ minimum. In addition, you can see what the Innovation Fund is holding before deciding to invest and how much. Traditional venture capital funds require capital commitment first and then hope the general partners will find great investments.

Subscribe To Financial Samurai

Listen and subscribe to The Financial Samurai podcast on Apple or Spotify. I interview experts in their respective fields and discuss some of the most interesting topics on this site. Please share, rate, and review!

For more nuanced personal finance content, join 60,000+ others and sign up for the free Financial Samurai newsletter and posts via e-mail. Financial Samurai is one of the largest independently-owned personal finance sites that started in 2009. 

Related: Why I'll Always Regret Selling My Business For Millions

25 thoughts on “Reflections On Making Money Online Since 2009”

  1. Thank you for sharing this advice and staying relevant. I could not have seen this time when a 9 to 5 job may not be the best option anymore for younger folks who are coming out of grade school and / or college. It has its limits.

  2. Thanks, Sam!

    Your strategy to go slow and write based on first-hand experience is what’s kept me reading your stuff and inspired me to do something similar for my blog. I’m now three years in, making ~$4k/mth on ~150k visits, having lots of fun and pursuing a mission I find meaningful.

    I thought I was on the right track…

    But then the stork dropped off our son last year. Just like you wrote about, I’m now feeling the pressure to do more to provide. But me and my blog aren’t as established as you and FA, and I’m not sure on what to do next.

    Did you ever work with mentors/coaches? Join a mastermind? Or something along these lines? If not, why? You’re a tennis coach, right? So wouldn’t it make sense to treat blog performance similar to tennis skills?

    Maybe this question’s for another post from you down the line. I heard you mention at the end of your enjoyable interview on the Tropical MBA podcast you plan to talk about online business and brand building more in 2022. I, for one, hope so!

    1. Hi Chris,

      Congrats on both baby and business!

      I haven’t worked with coaches or been in a mastermind group. I really just like to write what comes to mind and not get bogged down with the money . If I focus on money, then it’s no longer as fun to write.

      Maybe it’s because I have enough investments to generate passive income? Half the battle is just keeping on going.

      Now that you have a baby, I’m sure you’ll find a way to make more money if you need to. It’s the evolution airy part of us!


  3. Longtimelurker

    Sam, thank you for another great post. You are comfortably the best personal finance writer out there. It’s quite sad to see so many writers focusing on savings instead of earnings. Your information is fact based, aspirational, inspirational and you put your money where your mouth is. You have genuinely saved and earned my family and I 10,000’s if not 100,000’s. You’re a legend, keep it up!

  4. Sam – this post reminds me a lot of “10 years of unwavering commitment.” Very difficult to sustain something for 1 year, much less 10, if you don’t truly love it.

    Something I’ll add is the most daunting part about starting one’s own blog/website/etc. for many people is just getting started; at least it was for me. Sometimes the psychological barriers are cultural (I’m also Asian so deviating from “steady” or “predictable” paths does not come naturally) and sometimes personality driven (I would consider myself more modest so putting oneself out on the internet/Instagram/etc. is terrifying).

    To these I would offer some advice/reflections:
    1) Start small – one post can provide so much confidence to keep going. If you’re worried about the big, bad internet (police) coming after you, keep it to a small group or private at first
    2) Do it for yourself (a derivation of “do what you love and the money will follow” – if you’re writing/posting/etc. about something you love and you’d do it for free (or currently are), no amount of criticism can take you down. I firmly believe that. People can disagree, but ultimately if you are accountable to yourself and to yourself only, chances are you’ll never let yourself down.

    Hope you enjoy your well-deserved sabbatical! Looking forward to reading many more posts upon your return

    1. Yes, it takes a large amount of energy to start. I had that block for 3 years after business school. It took a dang global financial crisis in 2008-2009 to get me to start. I did so by hiring someone off Craigslist to get me going.

      That’s the thing, if you have trouble starting, hire an expert. Once you start, it’s much easier to build momentum.


  5. Hi Sam,

    You have inspired me to start a blog again. I wrote to you before and you helped me understand the seo part. My site is I wrote some personal finance books around the great recession as well and need someone to push me to write a blog. My friend, yo have accomplished that. I am soon going to put google AdWords in the site as well.

    I need to ask a favor and I am trying trying to help his Family out by adding to LinkedIn and Facebook and anywhere I can think of for our friend that recently passed away. There is a GoFundMe page set up for Milton. Unfortunately, he did not have any life insurance and his Family needs help with end of life expenses. He was a good man and talked like James Earl Jones. He probably could have been a great radio announcer. I was wondering if you can help spread the word as well or possibly help out. Sorry this is such a long e-mail. Just trying to help his Family out where I can.

  6. AnotherOnlineEntrepreneur

    LOL, I love the shade in the “You Don’t Need To Be An Expert Or Have The Best Product” section. I completely agree with you. It’s a shame you can’t just destroy these websites by letting everyone know these people have no expertise. I particularly abhor the people who make money teaching others how to make money online without ever having made money online before. Just ridiculous. But this lack of expertise can be found across the country. In general, 1% to 5% of competent people in this country actually know what they are doing and make this country rich and powerful. And it’s not the people always chanting “We’re Number One” or “Make America Great Again”.

    1. It’s not so much shade, it’s the truth. I really want people to know that there’s no need to wait to start. The key is to just start and figure things out on the way.

      The classic example I can give is Ramit Sehti. Just several years out of college, he wrote a book called “I Will Teach You To Be Rich.” Obviously, he was not rich then, but he became rich with that book and his online courses.

      If you can market well, you will do very well offline and online.

  7. Enjoy your sabbatical, Sam! Appreciate all your hard work in publishing articles. I have read all your posts since 2017. Your posts have inspired me to make sensible investments and also step outside of my comfort zone! I’ve wanted to start a beauty biz with some close friends since 2006. We might just make that happen this year or next!

    1. Great to hear Ceci! I might have to bring up some posts before 2017 to republish and update so you can read them too.

      And if you need help starting, just hire someone to launch!

      1. Thanks for the tip on launching our biz! We plan to open a medspa. I always enjoy reading your older edited posts. I also love reading the older comments and wondering how things went for others. Cheers!

  8. It’s quite amazing just about many online people really don’t know what made them successful. I read the mergers and inquisitions founder’s story and I think he attributed his success to something like “creating a great community by providing helpful content” or something along those lines if I recall correctly.

    I was shocked that he didn’t know the real, actual reason why he was successful. The reason is because his website and articles have great SEO ranking. Either he doesn’t actually know what made him successful or he wanted to put out a feel-good story for his readers.

    It’s really just in people’s heads. The criticism saying is “the blind is leading the blind”. Yeah but the blind leader still reaps all the rewards of being a leader, anyway.

    1. Starting early does help! I’m sure he knows his site does well in search.

      He has a fun story. He never said where he worked?

      Pretty interesting to build a business on how to get into banking after being sick of banking and leaving after just a year.

      I’m not sure I could sell people to enter an industry that I didn’t enjoy. I stuck it out in banking for 13 years and am not a fan.

      But it looks like he’s doing great and that’s all that matters.

      Anything is possible folks!

      1. It is interesting, yeah. One year of experience is all you need!

        I don’t blame you, Sam. I was in banking for 3 years and I had to leave. The personalities I met were just way too aggressive, “in your face” kind of personalities. They do pay very well though, that is a good upside.

        Yep! It just takes some time and the right kind of effort to make something stick and win.

      2. Would appreciate a post sometime on exactly what you did in banking. Especially for those of us not in that world. What did you and your firm do to earn all that money. Thank you!

  9. Great write up Sam, it’s been great reading your content over the years. While I have not started what I know I should, I appreciate the occasional pokes from posts like this!

    P.S would love if the “learn the fundamentals of online traffic acquisition” was in bold red letters


    Thanks, Sam for all the work you do. You have inspired us to continue along this path of Financial independence. Enjoy your sabbatical.

  11. Thanks Sam for everything that you do! You’ve clearly learned so much over the last decade. And have literally helped millions of us.

    Running a website is no easy task let alone writing consistent and informative articles.

    Lining up your sabbatical with California’s reopening is smart. I hope you get to do something fun and de-stress for a while. You deserve it!

  12. Enjoy your vacation! Thanks for your honest insights as always. Your right that if you are consistent and keep at it, your business will grow in the long run. I know this from personal experience with my most recent business. We chose the slow and steady growth trajectory, but it did work out really nicely in the end.

    I have to keep reminding myself of this with AR, since starting over is a strange reality after years of “success”. But this time my aim is to build that moat and not have to worry about an exit, when to exit, employees, etc.

    Anyways enjoy your time off. Writing this from my vacation. Now back to it for me.

  13. Sam, I *love* all your work and I sense our purposes are so aligned. Thank you for inspiring me. Your work encouraged me to start the Happy Asian Woman podcast/blog, helping Asian-American women find more joy in love, work and life. I don’t make money off of that venture (still haven’t figured that part out yet, but it’s good to know that the mental health space is profitable?! That was surprising to me.) I completely agree with you – life is short. Know when we have enough $ and have “succeeded” enough in our career. Enjoy the little things. Value parenting (love how you say being a stay-at-home dad is the toughest job you’ve ever had – I agree 100%). Speak up against injustice (thank you for speaking up for the Asian-American community #stopAAPIhate) Love your work and I look forward to many more years of following your endeavors!

    1. Hi Alice!

      Thanks for reading and great job on your site and podcast.

      Let’s link up before the year is out. Keep trucking away! I can totally tell you are loving what you’re doing.



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