When People Doubt You, Just Keep On Winning

When people doubt you, just keep on winning. If you keep on winning, people will eventually shut up and leave you alone. As a winner, they might actually start respecting you! But you don't really care because you don't care about prestige.

After 10 years of grinding away, one of my friends sold his business for $73 million at age 32. It was a bootstrapped business, so he ended up getting over 80% of the gross proceeds. Can you imagine? Wow.

When I asked him what he did with his newfound riches, he said he took a month off to go surfing with his buddies. After he got his fill, he then started a new software business.

When I asked him why he decided to get back into the grind so quickly, he responded, “I want to see if I can go do it again to prove to everyone and to myself that it wasn't a fluke.

During my financial journey, I've met so many people who have done extraordinarily well, yet continue to work all day and night because they know they were extremely lucky to have achieved their success. By replicating their success they also eradicate their guilt.

Their work ethic and self-awareness are both inspiring and concerning. But I empathize with my friend because I have the same desire to prove my doubters wrong all the time. It's in my DNA.

Once You Repeat, Nobody Will Doubt You Again

Let me share my latest story of ongoing doubt and eventual victory.

During my first year of coaching high school tennis, we got to the division finals and lost 2-5 to a school three times as large. At the time, my school had never ever gotten that far in its history.

My tennis friends ribbed me, saying it was a fluke that we had gotten to the division finals. After all, the division has 70 schools located throughout Northern California. To be one of the last two schools standing was surely luck.

I agreed with them because when you come in second, you might as well have come in last. We barely won in the semi-finals. I truly believed we got lucky to get so far.

Then in my second coaching year, we won it all and beat the team that had beaten us the previous year 4-3. This was our first division championship in school history and it felt amazing to be a part of this success.

Constant Ribbing By Friends

My tennis friends continued to rib me, however, saying our victory was still a fluke. I had my doubts it was all luck for us to get through the gauntlet. But I agreed with them. After all, there's always a first time for everything.

To think I had made even a speck of difference in the lives of the kids and the program would have been an arrogant assumption. I was just in the right place at the right time.

Then in my third year of coaching, we successfully defended our title and beat a powerhouse team 4-3 in the finals. Their #1 player got recruited to play college tennis and their #2 player is a 5-star recruit as a freshman. None of my seniors were college-level recruits. But we had good depth, great team chemistry, and maybe even some good coaching.

2019 was the second division title in our school's history. Defending a championship was harder than becoming a champion for the first time due to heightened expectations. It was also more stressful because we all wanted to prove that we weren't one-hit wonders.

Related: Where Are All The Adult Athletes?

The Ribbing Died Down

After the second division title, my tennis friends unexpectedly stopped ribbing me for coaching high school tennis. Apparently, they finally acknowledged I may have played a part in the victory as a coach. One even asked if I could hit with his middle school son and give him a recommendation.

My friends now even ask me for some tennis tips. Of course, I just beat them up on the court instead and make them buy me beer after for losing. “Here's my tip for you today buddy. If you played better, you would have won!”

Ah, winning feels so satisfying!

Oh yeah. I almost forgot to mention I got a lot of ribbing and worse on the internet too.

When the Internet Retirement Police this season said I wasn't allowed to consider myself a high school tennis coach for the past three years given I have Financial Samurai and retirement income, I used their disapproval as motivation to write a new post.

This post was called, How A Tennis Coach Provides For His Family In Expensive SF. It was picked up by several major news outlets and as a result, boosted Financial Samurai's traffic to an all-time high that month. Not bad for a coach. I'm thankful the IRP has helped me stay retired from the corporate world for a little while longer.

Maybe I'm just hardwired differently. But people's doubt gives me so much enthusiasm and energy! There is always a positive angle to everything. Like learning how to convince people you are bad to lower their expectations and then surprise on the upside! It's up to you to find silver linings.

When people doubt you, just keep on winning. How to overcome doubters in your life.

Keep Creating Small Wins

When you attract doubters in your career, your business, on the playing field, or in your personal life, all you've got to do is recreate your victory to hush up your doubters.

But more importantly, once you do it again, you'll hush up your greatest critic: YOU!

You will develop a tremendous amount of self-confidence to tackle many other things. In other words, your self-confidence is scaleable.

When I was a hiring manager, I always wanted the candidate to tell me a story of adversity and triumph. I'm a sucker for these types of situations.

It didn't matter how small the triumph was, like winning a July 4th softball tournament. I knew that someone who consistently achieved small wins could easily create big wins for the firm.

The same goes for all of you on your journey to financial independence and doing what you want with your one and only life. Paying off a car loan might be a small win. But once you do, you will feel empowered to pay off your student loans and then your mortgage.

Make Enough So You Can Do What You Want

Once you develop one passive income stream that generates enough to pay for your monthly gas bill, developing another passive income stream to pay for your monthly food bill is all but an inevitability.

Don't discount your small wins. Create more of them. Your small wins will snowball into greater victories.

Recently, I wrote about how difficult it is to become a professional writer. I was rejected by every literary agency in 2012, so I decided to self-publish my severance negotiation book. It has since gone on to generate over $500,000 in operating profits.

Then in 2019, an editor from Portfolio Penguin contacted me out of the blue to write a book. And I decided, if I was going to be locked down during a pandemic for who knows how long, I might as well write one.

Buy This, Not That, went on to become an instant Wall Street Journal Bestseller, an almost impossible feat for someone like me. But readers loved learning how to achieve financial independence sooner and tackle some of life's biggest dilemma's in a logical manner. You can pick up a copy on Amazon today.

Embrace the small wins. Eventually, they might become huge victories!

Finally, remind yourself that you don't need someone else's approval to go after the things that bring you joy. Yes, losing stinks. But more than the pain of failure is the regret you will feel for having never tried.

With enough courage and determination, sometimes you might even find yourself winning it all.

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

Related posts about winning:

For A Better Life, Be The Top 1% In Something, Anything

Are You Dirt? Then Stop Letting People Walk All Over You!

You Will Always Get Screwed, Just Keep On Believing

Being A USTA 5.0 Tennis Player

How To Survive And Thrive As Merit Gets Deemphasized

Having Absurd Dreams Is OK Because They Sometimes Come True

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32 thoughts on “When People Doubt You, Just Keep On Winning”

  1. Congrats on the victory!

    It’s amazing how the Internet Retirement Police consist mostly of privileged white women and some beta males who are all trying to leave their jobs, build their sites, and make money online but are failing.

    If you’re small and failing, the tendency is to join a mob to gain strength. But the funny thing is that the mob leader is the one using the weak to better her own financial position. Fascinating dynamics at play!

  2. Like they say, the sweetest revenge to to be happy and lead an even better life.

    The greatest self-doubt is indeed yourself and sadly the only way to quash that self-doubt is to repeat the same feat, at an even high level!

  3. Marie Jacobs

    Love the idea to just keep doing your thing no matter what the haters say and cracking up that the internet retirement police said you can’t call yourself a coach when you are paid to be a coach. I thought the internet Retirement Police only objected to calling yourself something misleading such as (fully) retired when also self employed or relying on a spouse income.

    1. The Internet police are a blessing. I couldn’t have come up with a lot of new content without them. Writers need inspiration, and they are inspiring!

  4. Really agree that small wins will snowball to even bigger ones down the line. They will boost up your confidence and make you feel that you can achieve anything.
    For me personally, I ignore noise from doubters and focus on what I’m doing because they can get you off that focus. But we’re all wired differently where some that more motivated by listening to doubters…as along as we achieve our end goal then that’s all that matters.

  5. Great post and congrats, Sam! It’s definitely the “Doubt” of others that’s usually the best motivation. It’s pretty similar to the preference of “Loving to Win vs. Hating to lose” as your top competitors typically fall in the latter category. Maybe it’s due to the feel of losing to your haters and doubters predictions.

    Best of Success

  6. I loved this! Some of my favorite phrases that come to mind are: “Put up or shut up” and “Money talks and bulls**t walks” — No one can grind like you can, Sam. I hope you keep writing even if you do move on from FS one day. Keep winning either way.

    – DeForest

  7. I sold a mobile app side gig for very low 7 figures in 2013. Who cares? It was a fluke to some extent. But I built the business to a point some other business thought it was necessary to acquire. So…I sold it by having lots of luck and a little bit of business acumen. Will I ever replicate it? Probably not…but I don’t really care. Just like you, I’ve taken that money and invested in rental property and airbnb property…that throws off over $100K/year.

    I don’t really care if anybody judges me. Don’t care if they say it’s a fluke….because I’ll agree with them…but I will also mention to them that during my start up times, you could catch me at 2am on a Saturday morning working on user interface designs or conference calls with my asian development team.

    Working hard to build something that’s a success….even if it is only one big success is well….successful.

    1. Congrats! No curiosity in trying to do it again?

      I like to try again because there are so many missed steps that I made that I won’t make the second time around. It’s a big curiosity.

  8. Great point made here — If it brings you joy, everyone else can pound sand! Heck, even if it’s a day job complete with cubicle — it’s entirely possible.

    My father in law still coaches three sports in his retirement. It’s essentially a part time job that keeps him busy the entire school year, but he LOVES the impact he has on kids, and he loves that the work keeps him safe from boredom. (It doesn’t hurt either that his teams often contend for championships).

    1. Very cool about your FIL. Three sports is a lot! But the fulfillment is quite fulfilling.

      I’ve found that the more you work with other kids, the better you’re able to parent your own kid because you are put in more situations that forces you to learn on the job. The more you’re prepared, the better.

  9. Hi Sam!

    I have been a lurker on your site for a while now, so this will make it my first response. It is certainly amazing how you describe the struggles of high achievers such as yourself on a daily basis. Long after accomplishing big goals, it can be extremely challenging to avoid self imposed doubt and, of course, doubt from friends and/or family. It has been extremely helpful for me personally to learn from your lifestyle in SF and how you achieved FI in such an expensive city. Your career in Finance and your stories in the industry has been extremely helpful for me to navigate my day to day job. I currently do software development for a Fin Tech here in lovely San Francisco. Most of your stories in Finance hits right at home . Be sure that your words are speaking to some of us out there who are still grinding their way out of the big wheel.

    I hope you and your family had a peaceful long, cozy weekend.


    1. Thanks mate! If the direction is correct, sooner or later you will get there.

      Hope you and your firm experience much success.

      The grind is definitely long. But it’s usually worth it in the end. I don’t know anybody who regretted working hard for something they believed in.

  10. Great post once again Sam! I think this speaks volumes into how society is structured to build jealousy and doubt when someone is getting ahead in life. Coming from a Asian background of highly educated parents, my blogging dream is viewed as complete waste of time lol, but as a Canadian millennial I see there’s such a void in the relationship of money towards the general public, especially in Canada, therefore I set out to fill this void so to speak. I have given up on explaining myself, rather I absolutely enjoy the lonely late nights I spend on reading, writing, researching and learning about the blogging world. Keep up the good work Sam, and remember when a lurker like me leaves a comment you know you’ve more supporters than just on the surface :-)

  11. When I was in college, I studied Global Affairs. I applied to and was awarded a paid internship abroad with the US Embassy Consular Affairs London, England. In the same year, I applied to and was awarded a student Ambassadorship to study and explore culture abroad in Italy. The following year, I did it again and was awarded an all expense paid trip to explore South African culture and water disparities sponsored by Coca-Cola. ☺

  12. Sam in the pod you mention that USC is an “ok” school. It’s ranked #17 in the Wall Street Journal and #22 in US News (tied with Berkeley). I would say the school deserves a better connotation than “ok”. Yes, I took it personally as I am an alumnus and got into Ivy League schools as well.

  13. Yes!!! Congrats on those championships. I coach basketball rather than tennis, but in both sports the adage holds true that a coach is only as good as his players. No one can take bad players to a championship. BUT, where the coach makes a real difference is in the margins, the little things that tilt the scales from losing 3-4 to winning 4-3. Maybe it’s helping your #3 player get more confident with his serve that allows him to hold on for the crucial victory, or developing a winning strategy with the doubles team based on your diligence in pre-scouting their opponents.
    Great coaches look for all the angles, and when you reach the stage of the playoffs where all the players are good and the margins between them are small, that’s where the coach’s contributions make all the difference. That’s where hard work and diligence pay off.
    The same is true of other endeavors — the margins between success and failure in business, or blogging, or investing are often small, and the reason some talented people make it and other talented people don’t is that the successful ones do all the little things they have to in order to find an edge, and never rest on their laurels.
    Congrats to you for keeping your edge, and inspiring the rest of us to do it as well.

    1. Thanks! And I agree.

      The critical decision last year was blowing up our lineup to counteract a strong team. We put guys in new orders to squeak out the 4-3 victory.

      This year, my fellow coach wanted to change the lineup and break up our #1 dubs team and have one play singles and have a new doubles team.

      I was adamant we go straight up with our lineup and my fellow coach agree. It was huge bc the opposing team dumped their #4 singles player, so we would have wasted our guy at #4 singles and may have lost #1 doubles, which we won.

      Small decisions matter!

      Awesome you coach basketball! My favorite game. But I didn’t have the confidence to try out and just focused on tennis. GL!

  14. Fire Year FIRE escape

    Wow Sam, you are really impressive.

    Finding the small victories is I think the only way to get yourself to the big victories. When I was chasing FIRE I celebrated every time I got 1% closer to the goal. It kept me going. It’s no tennis championship but I still think its pretty awesome. :)

  15. Congratulations to you and the team. That’s not a fluke. You guys consistently performed at a high level. Great job.
    I’m not wired like that, though. Doubters don’t fire me up. It’s discouraging to me so I just ignore them. I don’t need to prove anything to anyone.

  16. Congrats on your successes Sam! It is definitely very satisfying proving doubters wrong. I worked hard to prove doubters wrong in stage performances during my student days. In college I wanted to prove that it’s possible to graduate in less than 4 years and I did it in 3.5 years. That was very satisfying.

  17. My small win?

    It’s a bit silly really. I do triathlons, mostly to see if I can actually do it. It’s not just the physical side of it but the mental game as well.

    Last year I was signed up to compete in the western Sydney 70.3 (1.9km swim, 90km bike and 21km run). My training leading up to it was impacted by all sorts of life events. My father passed away, our 4th child was born and my third had an operation. All within 6 weeks of each other and all within a month of the event.

    I knew I was totally unprepared both physically and mentally. But I also knew I thing – I was going to finish the event. No. Matter. What.

    And you know what? I did. Even after I injured my foot 1 km into the run, I managed to hobble around the course and ran an hour slower than expected.

    I finished near the back of the pack in one of my worst times ever. But I finished and after everything that had gone on, that was the sweetest victory I’d ever had.

    1. Jim –

      After all those life events, I would say that was a BIG win! NOT silly at all. Congratulations on your accomplishment in completing the race.

      Congratulations on the birth of your fourth child. Hopefully your third child’s operation went well and they had a smooth recovery. Condolences on the loss of your father. Such an emotional roller coaster in a span of six short weeks.

      You are a warrior!

  18. Congrats on the win!

    I, too, am driven by my doubters and my haters. They give me the fuel to keep on going whenever I feel lazy.

    The Internet Retirement Police are so funny. It always amuses me how some people have nothing better to do with their time. The police force seems like it’s formed by a bunch of losers.

    Smart to use them to drive traffic!

  19. bluegreenguitar

    Dear Sam,

    Congrats on all your successes and thanks for sharing them – it’s inspiring and motivating! I also appreciate your perspective – it’s refreshing and a good solid alternative to a lot of info online about investing/career/life.

    I too have a friend that just had great business success. He took about 1-2 months “off” and now he’s working on a new business that he wants to grow like the last one. Besides travel adventures, starting a new, high-quality business is probably one of the most exciting things a person can do in modern society, given a specific personality-type.

    Coaching sports is a lot of fun, too (I was a coach for a 1 year/ tutor 2 years), and I still remember all my coaches (and teachers) from 10-35 years ago – so congrats!


    Off-topic -> My (un-expert)2 cents/questions – I’m reading some of your articles and it sounds like you’ve thought about/at least considered selling Financial Samurai and starting a new job. Please allow me to share my (highly biased (as a FS fan), fairly uneducated) opinion (that it would probably be better to continue developing FS.com than to sell, assuming you continue to enjoy creating FS.com).

    I made a spreadsheet b/c I was curious about the results. I’m sure you’ve done similar projections, etc.

    Again I’m not an expert, nor is it really my place to decide. It’s just the biased two cents from a fan/reader :)


    Basically I think this is a great website/business.

    If you want and like to continue creating FS, I think FS.com could be great for a long time, in terms of finances, personal fulfillment (hopefully), quality, and reader/customer appreciation.

    There’s tons of possibilities:
    – new books,
    – edited /curated books based on past FS.com content,
    – consultations,
    – coaching (it sounds like you’ve got some skills),
    – conferences,
    – other products,
    – your own app :), etc.

    In terms of additional types of FS.com content (I like content as is FWIW):
    – success stories from readers that have followed FS.com principles,
    – occasional guest posts,
    – “outsource” certain aspects


    I’m sure you’ve run the numbers.

    But I ran some numbers just for fun :)

    Based on your article (https://www.financialsamurai.com/ranking-the-best-passive-income-investments/), I see that you rank:
    #1 Your Own Products (To earn $10,000 a year in passive income would therefore need roughly $250,000 in capital),
    #2 Real Estate Crowdsourcing (7 – 13% annual returns based off historical data),
    #3 Dividend Investing (~1.8% dividend yield … to … 6.5%).

    So after taxes, to make equivalent numbers in the other types of passive incomes, the business would need to sell for about between 7x-55x (based on between 1.8-13% returns) to return the same amount. You use 25x in your example in Your Own Products.

    Not being a business consultant, but just a casual reader, I bet you could probably bring a smaller product to market once a year. Maybe consider writing 2x/week for the “blog” and 1x for the book/product?


    Let’s say FS.com had 1 new book a year – with an optimistic, but conservative, continued sales number of $10K/year.

    In 10 years, FS.com could increase pre-tax sales by $100K/year and value by $2.18-2.5M(25x). Of course, you’d have to take into consideration time/energy invested. In that 10 year period, you’d also (pre-tax) earn an extra $419K.


    Say you sold FS for 25x.

    Then got a job, etc and spent the same amount of time/energy on job as you would have spent on FS.com.

    Assuming interest/investment rates were 4% ( basically 25x), then the sale of FS.com vs holding would result in the same amount of money earned.

    Still assuming passive income earned 4% – to have equal financial returns, that new job (in theory) would need to net (in 10 years) 25x whatever long-term passive income you could develop on FS.com, (with the same time/energy) though obviously there’s tons of other benefits, etc, too (in either scenario).

    I’m not taking into account risk/diversification, etc. Also, I don’t really know how much time/energy would be spent on FS.com vs Job, so I don’t know results for sure. And, of course there’s tons of other factors, such as personal preferences.

    But here’s some numbers to get a feel for possibilities (though I probably messed up calculations in someway)-> from https://docs.google.com/spreadsheets/d/13DLrhiM2nHpv39w558hiXAvUWD9hXnBkZSzbSTaHwkw/edit?usp=sharing

    After 10 Years =>
    SCENARIO #1 ($270,000 job, 4% Interest on Investments, 25x valuation, 30% tax rate (on earned/unearned), $10K new yearly product)
    #1 $270K Job = $2,146,822.36 Value, Yearly Passive Income = $53,325.90
    #2 $10K/year FS.com = $2,169,224.06 Value, Yearly “Semi-Passive” Income = $79,511.94

    SCENARIO #2 ($480,000 job, 5% Interest on Investments, 20x valuation, 35% tax rate (on earned/unearned), $20K new yearly product)
    #1 $450K Job = $3,392,048.73 Value , Yearly Passive Income = $97,564.49
    #2 $20K/year FS.com = $3,389,456.85 Value, Yearly “Semi-Passive” Income = $150,757.72


    I don’t really know – obviously it’s a personal decision but as a fan of FS.com, I’d thought I chip in my opinion!

    Passive Diversified Income has tons of upside in terms of lowering risk and energy expended but not as much income potential/risk as personal business income such as FS.com.


    And that’s not including joint business ventures, t-shirt sales :), conferences, coaching fees (probably easily $100-300/hr), etc.

    I also think there’s probably niches for products for/coaching/advising people who just IPO’d, and for people who are experiencing inter-generational wealth transfer. You’re probably well-positioned to coach these people, as well.

    Obviously you have a more experience with FS.com, valuations, etc. But I thought I’d lend my 2 cents – I hope you don’t mind!

    Anyways, thanks for all the great content and best wishes in all your current and future endeavors!

    1. Great thoughts!

      Bottom line: The upside is endless if one has the energy to continue. I agree with most of what you have written. Do you have a business of your own?

      After so many years running Financial Samurai, it’s easy to take a couple weeks off and the sidewalk continue to run as operated because of all the content that has already been produced. That is the beauty of the Internet and search engines. I’ve also got a backlog of about 10 posts or so.

      Let’s see what happens!

      1. bluegreenguitar

        Thanks! I don’t really own a business. I’m more of an “independent contractor”, if that’s what being a musician is called these days!

        Agreed – that is the beauty of the internet!

  20. Great story! And congratulations. I totally hear you on site wins snowballing into bigger ones.

    Once I landed a small account at work, I was able to land bigger ones.

    It really does take courage to go for what you want sometimes.

  21. Great motivational post Sam.

    You are right that one event can often snowball into making great strides in subsequent things.

    When I paid off my medical school student loans (a full 17 years after I graduated (way too long), something clicked in my head and then I tackled my 2nd, and subsequently 1st home mortgages. That was the kicker and I became debt free.

    Then I started hearing about passive income streams and thought I had found the fountain of financial knowledge I have been searching for.

    The first passive income stream was minuscule compared to my W-2 income but it soon snowballed and now it is getting to the point where I can actually consider early retirement (it is still a small % of my W2 income but fortunately I never needed that much money to live anyway).

    I absolutely love your tennis coaching story. You definitely have silenced your doubters.

  22. Great article Sam.. my career path was motivated largely by wanting to prove wrong the naysayers

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