The Best Time To Start A Business: When You Are Young, Broke, And Naive

The best time to start a business is when you are young, broke, and naive. Once you are wealthy and know the cruelties of the world, your enthusiasm for starting a business will fade.

Since I was 12 I've always wanted to be an entrepreneur. I was surrounded by kids whose parents started beverage companies (e.g. Yeoh's) or launched wonderful resorts (e.g. Pulau Tenggol) while living in Kuala Lumpur, Malaysia.

They lived in nice homes and drove fancy cars. I was smitten. Yet even when I was given a clear opportunity to go to China for a startup opportunity in 1999, I couldn't say “yes” because I was scared and received an offer from a bulge bracket firm in NYC. Nobody turns down Goldman Sachs right out of college so I toiled in the finance world for the next 13 years.

I've always wondered what my life would be like if I took the entrepreneurial path instead. My Mandarin would be excellent, that I know at the very least. Maybe I would have been prescient and bought as much property in Beijing as possible before prices rocketed through the roof. Maybe I would be thrice divorced with multiple children given the rules of business engagement are quite different out East. Who knows, but it's always fun to pontificate.

Best Time To Start A Business: After Some Work Experience

By the age of 35 I decided I had enough of working for someone. Although I was scared of leaving the comforts of a handsome income, I also knew I'd regret not finally giving entrepreneurship a go in my 30s. Unlike being a nubile 22 year old, I was an industry veteran in finance with an MBA and a large financial safety net thanks to all those years of savings. What was there to lose except for everything?

Major props goes to those who start businesses after becoming a parent. If I ever become a father I think I'd be so focused on not messing parenthood up that I'd leave little-to-no time for entrepreneurship. As a result, my chances of making it as an entrepreneur would be slim-to-none. I'm a very focused individual who is unwilling to fail due to a lack of effort.

As soon as I left Corporate America in 2012, I began writing twice as much on Financial Samurai. I created a brandable product on how to negotiate a severance package within the first four months of being free. It's now newly updated and sells $5,000 worth a month.

I can't believe my luck, but Financial Samurai overall generates more income than I made as an Executive Director in banking while working 90% less hours and having 100% more fun!

Always Felt A Little Too Lucky And Somewhat Guilty

Despite the 70 hour workweeks on Wall St. and the intense stress, I've always felt like I didn't fully deserve to make the money I was making. Income is obscene compared to every other industry I know of.

Working for a corporation almost felt like CHEATING. I didn't build any products at Goldman Sachs, nor did I do anything to establish its reputation. All I had to do was get in, not screw things up, and a six figure income was mine after the first full year of work. I'll write a post about getting into Wall St. at a future date if interested.

Meanwhile, I saw my friends launch startups out of nothing. One classmate created, a now defunct internet consumer company targeting college kids. They sold things like lava lamps, condoms, and bubble chairs. Throwing campus parties was their marketing strategy. Sign me up!

I loved the idea and was so close to investing $20,000. Even though their company went bust two years later during the 2001 dotcom flameout, I always highly admired them for taking risks when I could not (China offer).

I wanted to create something out of nothing as well. If you think about it, every single company had to be created by someone. I guess Wall St. folks are pros and creating something out of nothing (a dig), but I wanted to create something that was consumable, helpful, and long lasting. This is where content creation comes in.

Writing As A Product

Although some of you may not feel like my posts are “products” in the traditional sense, to me they absolutely are. I look forward to sharing the knowledge I've garnered in finance with all of you as well as look back on my writing when I'm old to have a chuckle. Although typos exist all the time, I do my best to create as much quality content as possible. Please shoot me an e-mail or leave a comment whenever you see one. I'll fix it right away.

Besides, I've self-published a book that generates between $40,000 – $50,000 a year in passive income. Further, I've signed a traditional book deal with Penguin Random House to publish a book in 2022.

Because working for a corporation felt like the easy way to make money, I also wanted to prove that I could make six figures on my own. It took four years of consistent effort, but I can check this goal of my list thanks to my websites. If you are thinking about going off on your own, please establish an online presence by at least registering your name and building your profile. A good idea might not come for a while, but I trust that if you think long enough something will appear.

Funny New Feeling

The issue I now face is that it feels off making money while not suffering like I once did in finance. Sure, I'll have down moments as I wrote in this post, but shouldn't I feel the dread of waking up in the mornings to go to work or the pain of flying six hours across the country in a middle seat to take a difficult client out to lunch?

What happened to the initial hardship when I explained that a day job is so much easier than entrepreneurship? I used to be fine with every inconvenience as a bright-eyed 20-something year old.

I was hungry to build my financial nut and naive enough to believe I could change the world. Now I'm a saltier veteran who still has a fading glimmer of enthusiasm emitting between battle scarred eyes.

Stay Broke To Keep Motivated

The best time to start a business is when you have no money. When you have nothing to lose, it's easy to take more risks and give it everything you've got.

It's much better starting from nothing and becoming wealthy over years of sweat and tears than inheriting lots of money. The first way gets you to be more appreciative of what it takes to make money while the second way leads to disillusionment. How many people do we know suddenly come into a lot of money only to piss it all away? (Read: What To Do With A Financial Windfall)

There's only one problem with working so long and so hard for your money. Sooner or later you will lose your motivation no matter how in tune you are with society. You'll start believing that you deserve everything you've got. You'll begin to take ridiculous amounts of vacation because what do you care about work?

Inane things like a government shutdown makes you feel better because suddenly 500,000-800,000 more people are kicking back as well. You start putting off clear opportunities because you just can't be bothered to put in the effort.

As my passive income streams grow it's becoming incredibly difficult to stay motivated to make more. I know I should be doing a better job monetizing Financial Samurai, but talking about unmonetizable topics such as fatherhood and complicated relationships is so much more fun.

I'm kind of sick of watching all my financial accounts, which is why I have a free online software system to do it for me by sending me weekly net worth updates over e-mail.

I'm also much more amenable to paying a financial adviser 1% of my assets so she can look after my money as I concentrate on living a free life that has nothing to do with making more money.

The Biggest Reward Is The Journey

Take it from someone who reached his financial goals early on but is struggling to want to make more. Yes, this is a first world problem. Part of me wishes I didn't financially peak so soon in my early 30s. Instead, it would have been nice to work a little longer until 40-45.

I wouldn't have had to sacrifice as much in my 20s for financial freedom. It's like investing in a terrific 20% IRR asset for 13 years and suddenly getting all your money back. What am I supposed to do with the capital now? I also let honor and pride keep me on a much harder route than I should have.

I look to my blogging colleagues who sold their websites for millions of dollars and guess what they are all doing? They all continue to write for their sites they sold years ago! They just can't stay away because blogging was such a big part of their lives for so long.

To replicate their success in other avenues would be very difficult so they stick with what they know. One friend confided in me that he wishes he didn't sell so early right after the financial crisis. He longs for complete editorial control and perhaps much higher valuations now that the bull market is back. Peaking too soon can be a curse because nothing may ever be as good.

It doesn't matter whether you're a grocery story clerk who is trying to scrounge up enough money to live on his own or you've got $1 million in investable assets. What matters most are the little behavioral changes you make and the financial milestones you achieve.

When you're in the moment, you feel the most alive because this is all you know. If you're not in the moment you start becoming apathetic to those around you.

Related posts:

Five Sure Signs It's Time To Move On From Your Job

The Best Time To Start An Online Business

It's been over nine years since I started Financial Samurai and I'm actually earning a good passive and active income stream online now. The best time to start a business is today. The global pandemic has shown us that no job or income stream is safe. If you can start an online business, you should be able to weather the storms much better since it can't be shut down.

I never thought I'd be able to quit my job in 2012 just three years after starting Financial Samurai. But by starting one financial crisis day in 2009, Financial Samurai actually makes more than my entire passive income total that took 15 years to build.

If you enjoy writing, creating, connecting with people online, and enjoying more freedom, see how you can set up a WordPress blog in 15 minutes with my step-by-step tutorial. You just never know where your journey will take you once you start building your brand online.

It's all about leveraging the internet to be free and grow your wealth!

Pro Blogging Income Statement - The Best Time To Start A Business is today
You can start your site for next to nothing and potentially make a lot of extra income. This is a real example.

Recommendation For Leaving A Job

If you want to leave a job you no longer enjoy, I recommend negotiating a severance instead of quitting. If you negotiate a severance like I did back in 2012, you not only get a severance check, but potentially subsidized healthcare, deferred compensation, and worker training.

When you get laid off, you're also eligible for up to roughly 27 weeks of unemployment benefits. You may also get enhanced unemployment benefits as well. Having a financial runway is huge during your transition period.

Conversely, if you quit your job you get nothing. Check out How To Engineer Your Layoff: Make A Small Fortune By Saying Goodbye.

It's the only book that teaches you how to negotiate a severance. In addition, it was recently updated and expanded thanks to tremendous reader feedback and successful case studies.

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55 thoughts on “The Best Time To Start A Business: When You Are Young, Broke, And Naive”

  1. This is really great.. when I was a 12, I did not know.. whats money… business.. why we need that. Starting early is always good. You have more opportunity to correct your mistakes and experience to do something better… I still working hard and smart to make something, I want.. :) Thanks for sharing.. Good article..

  2. This is such a great post for me at this point in my life — so close to quitting my 9-5 but also getting ready to welcome two new k ids in the world in a few short months. I’ve never been so motivated to make it work because the last thing I want to do is go work in a cube when I could be home with my kids and making an income online.

  3. “Nobody turns down Goldman Sachs right out of college” – orly? So I’m not anybody then, eh? =P

        1. IT at GS? Or you went to a tech company instead of GS?

          The back office can’t be that badly compensated. But the upside is limited. Best to join an investment bank to be an investment banker and not a IT guy.

  4. I think it’s a grass is greener thing. There are tons of 20-somethings willing to go work for “the man.” Plenty do when their startups get acquired in talent acquisitions. Likewise, it’s easy to think that as a 30-something corporate worker you should have started a business when you were younger.

    All in, corporate work and entrepreneurship are almost always overrated by people who work on the other side. That’s just my opinion.

  5. It is definitely easier to take some career risk when you have the financial backing of a large investment portfolio. If you fail, and nothing material changes in your lifestyle, is it really a “risk”?

    I look at working at something to make your bucks first, then striking out on your own as a surefire way to at least meet your minimum lifestyle requirements (food, shelter, entertainment, etc) and then have fun with startups, biz ventures etc.

    1. You’re right. My risk is only time and frustration. Maybe some embarrassment too if I shut down.

      Hopefully folks don’t go crazy and take on massive debt to pursue their entrepreneurial endeavors. Only sure things or close to sure things when debt is involved!

  6. I believe the key here, aside from having a good entrepreneurial idea and the passion to pursue it, is having a mentor. At my last employer, such mentor – mentee relationships were encouraged…even reviewed during the annual self-assessment process.

    BTW, what is your opinion on business start-ups such as Shark Tank, or starting your own Yakezie business start-up investment group?

    Now onto your blogging colleagues…”my blogging colleagues who sold their websites for millions of dollars.” I just can’t believe these plain vanilla sites sold for millions of dollars. I don’t know about you (well yes, I think I do know some viewpoints about you now), but after a year of so of reading financial blogs I’m getting tired of the same old re-hashed financial tips. They are [yawn] so boring. I appreciate your different viewpoints here. I guess there is enough “new eyeball” churn to keep the other blogs readership up. [GRS just seems so amateurish now]

    Since I’m FI now, I should pull the trigger and start my own blog…but fear not, it would be about more than pure FI. Now to find the motivation… :)

    1. Here’s the thing, every year there will be millions more people graduating from high school or college who need help with their finances. The blogs who sold for millions are very smart to go plain vanilla as I said in a previous post. They attract the majority of readers. Hence, if I want to grow, I need to talk about budgeting, saving, paying off debt and stuff. To deny the obvious would be silly for me.

      And if GRS sold for $10 million +, I think you’d agree that boring is very, very good :)

      1. Who / what company bought GRS? If public, I gotta believe it would be a good short in the near future as the financial blog space becomes a dime a dozen. IMO, JD sold at a good time, for a great price.

        1. A publicly traded company right here in the Bay Area :) Anybody who sold any asset before this year sold at a lower price than they could get. Can you imagine selling anything during 2008-2010? Everything is up 50-150%. And to be clear, $10 mil is conjecture.

  7. Motivating kids to start a business early is a good way to start them off, because the energy is there, you just need to work harder on the drive. Though, with some kids these days, it’s difficult to see them with the kind of hunger that motivate people in the past.

  8. Working in the tech industry, my big turning point was buying a home.

    Like many big decisions, I didn’t fully understand the ramifications when I made it, which are crystal clear in hindsight. Certainly, I’m saving money, building equity, and living a more stable life. But every so often, I do get the itch and wonder what my life would have been life if I’d stayed more mobile – where I’d be living, what I’d be doing, and who I’d be doing it all with.

    But that said, I look at my life, and it’s a damn good one. Accomplished much, and looking forward to a lifetime more to come.

    After all, it’s only too late when you think it is.

  9. Chris Guthrie

    Hey Sam,

    On this point:


    That’s specifically why I bought a house for only $130,000 when I make a six figure income that’s been growing every single year since I left my day job. I’m intentionally holding back my personal expenses so I can save more, invest more in my business and not expand my lifestyle.

    I have a lot less stress paying a $1,100 per month 15 year mortgage and it allows me to focus on just building a much larger business so that if I do sell one of my businesses I can wait until when I do sell it’s for instant financial independence (if I want it)

    Great post though,


    1. Isn’t that the opposite of what I’m saying though? With so much disposable cash, I would be less motivated. If you bought a $600,000 house and had tighter cash flow, im thinking your hunger might be even higher!

      1. I think I agree more with Chris here.


        I understand what you are trying to say, but I think being broke just kills your flexibility as a small business person.

        You need to be able to afford to experiment with new products/services. That requires lower cost lifestyle and lots of capital. Most new businesses fail due to be under capitalized.

  10. The best time to start a business is when you are ready. It usually starts with an idea, you either have the skills/talent or the partners to start a business is when you should start one. If the idea is good enough, you can find or get the money. There are a huge group of people who are risk averse and they should stay in their corporate job and that is the way it should be. You have to believe in something enough to overcome your fear.

  11. Thanks Jeremy. I definitely do not recommend quitting your job to do something entrepreneurial right now. Just work on stuff part time so you realize how brutally difficult it is.

    Having the luxury of a day job income is fantastic for entrepreneurs. Go for it only if there is a good amount of traction and worthwhile income coming in. I’ll have a post about this in the future on when to quit.

  12. We’re hoping in our mid-30’s we’ll still have plenty of energy to keep working on projects together, including new businesses. Our goal is that by having (hopefully) already reached financial independence, we’ll have more flexibility to pursue projects and businesses that interest us rather than ones that we absolutely HAVE to grow X% YOY to be able to buy groceries. And hopefully that flexibility lets us try new and innovative things… which sometimes will succeed, and sometimes not. But we might not know without the freedom to try. =)

    1. It’s definitely worth a shot, that’s for sure.

      But I can tell you now that once you reach financial independence, it’s very easy to shy away from doing anything you don’t 100% enjoy doing. And doing something for money becomes very secondary on one’s list.

      Good luck!

  13. The great thing about being young is the energy but laziness is also common too. There will always be challenges at any age with starting and maintaining a business. But it’s never too late to start and follow your heart! One has to be able and willing to work hard, sacrifice and grow from failures.

  14. As someone who is in their mid 20’s, I really, really would like to start my own business. I have time, energy, ambition, I am an extremely loyal and dedicated worker (my parents instilled some great old-fashioned qualities in me) and I know I would do a great job and bust my butt on it. The only thing I am missing is an idea/starting point, and the frustration from that alone is immense. Then I start doing the “If only” thing. If only I could figure something out. If only I could think of something, I could leave the corporate mess. It’s actually quite stressful, and the stress is for nothing – quite literally. The corporate world has drained my boyfriend and I (we’re too young to be this bitter, I’m told). We think having our own business would be good for us. We just don’t know what, and it aggravates us to no end.

    We just (yesterday) finally came up with the name we’re going to use for a joint travel bog. We had wanted it up and running with a few articles before our trip to Peru at the end of this month. Because we only just came up with a name for ourselves, we may or may not miss our mark with those beginning articles. We also don’t plan on monetizing it for quite some time, because who knows if our writing would be worth money. We also want to see if we’re still 110% for it before we start trying to wade through money stuff.

    I hate to say we’re desperate, but I think we’re getting there. We want out before we crack under the pressure of corporate America (I’m tired of this grey-walled cube farm). We hope for a successful blog, and a successful “other income”, our own business, for our main source, if we could just think of something! We are at the perfect point to do it!

    To answer your question, in my opinion, the early 20’s is the best time to start a business because I haven’t gotten to an older age to try it out yet. :)

    1. Good job coming up with a name! You’ll find that once you launch the site, and pick the theme, colors, tagline, and design, your creative juices will begin kicking in.

      I think you’ll surprise yourself with what you come up with! Good luck.

  15. Good article, Sam

    I can definitely see that the 20s is a great time to start a business, but I’m not sure if it’s so much an age thing as a “phase of life” thing. I started my biz when I was in my 30s and I still had a lot of energy and time, but only because I was still single with a low “lifestyle cost”.

    As far as motivation after financial independence, I think that’s a tough nut to crack. You really have to be a high-energy person to accomplish something when you’re in that state. Either that, or if you do accomplish something big, it would all be powered by a burning desire to make an impact in some way. I’m sure the majority of the people simply don’t have that big WHY, especially as they get older.

    I’ve mentioned that before in previous posts, about my search for a worthy post-FIRE BHAG (Big Hairy Audacious Goal). It’s a tough question at the best of times. Then, throw in a large passive income, sunny days, a nice bottle of wine, and I can see that search stalling out quickly.

    1. Yes, perhaps it is a stage in life thing. Like how some people don’t grow up until late or start saving for retirement until their 40s etc.

      When you don’t have to so anything for money, it’s difficult to start anything. Hence, never tell our kids they have a trust fund or you have money!

  16. another great post.

    @Jane…on the topic of typos…somewhere in the middle of the post, I contemplated the difference between eyes which are ‘battle scared’ and ‘battle scarred’…

    I would believe the great Samurai Warrior meant Battle Scarred. ;)

      1. “…I’m also much more amendable…” Did you mean “amenable”?

        Typos in blogging are no biggie, we can figure out what is meant. But it says a lot about your ethic and effort towards quality that you encourage correction, even on typos that spellcheck wouldn’t catch like ‘scared’ or ‘amendable’. Also, I wonder if the ‘guilt’ you feel might instead be a strain of ‘appreciation’? You had an opportunity/accomplishment/compensation that few get, and made the most of it. Save the ‘guilty feelings’ for the decades to come, Sam, there will be lots of time for regrets later!:-) Continued success to you.

  17. moneystepper

    I often what I would have done if I hadn’t got the required degree for my job in the finance sector. I’m pretty sure I would have done something entrepreneurial, but I’m not sure what.

    I would be interested to hear more on the getting into Wall St. post…

  18. These are all extremely valid points. I had some success starting from scratch a few years ago. Sometimes I regret that I had that success at all because all I want to do is to chase those highs. I’ve also had a successful career as a professional. Some years my “hobbies” have made me more than my professional career. None-the-less, I’ve always continued to pursue my career.

    Now I am also addicted to being entrepreneurial. Some people play golf, I build websites. I have no monetization plan for my next project. I’ll run it at a loss until it has value to someone. For me its more about the validation than the income. I can also identify with feeling lucky/guilty about my professional career. In fact, when I was younger I knew that I was being way overpaid for my age and experience and had a hard time wrestling with that concept.

    It’s true that with some success comes apathy and the idea that you just can’t be bothered to put forward a true boot-strap effort. A little bit of outsourcing will usually remedy this because I ultimately feel more efficient. But, if I don’t have a side project going I will begin to feel depressed. Like my life is without meaning.

    1. I’ve hired someone to work with me to build for her expertise and for her energy to get things done. Hope it’s a good partnership!

      I wonder how many other people feel lucky/guilty with making the money they make in their profession…

  19. Good post Sam! I sort of see this from two sides. I would generally agree that in terms of starting a business the younger you do it the better. You’re generally more risk tolerant and may not have a family so you can get by on less and roll with the punches more.

    On the other side, I just left corporate America about 18 months ago to help my wife run our business that she started three years ago and we have three little ones under the age of six. Typing that, by the way, makes me want a drink, Lol. ;) However, it has been great for us because I have that experience and education to fall back on. If we would’ve done this ten years ago I think we would’ve flamed out, but now I have a confidence and we’re seeing the business grow by leaps and bounds. All that said, I think it can be done either way, but the sooner you have that opportunity the better you are for taking a jump at it.

    1. LOL!

      This is great that you’ve joined your wife full-time and your business is growing.

      I guess the flip side is that you wouldn’t have three little ones under 6 if you started in your 20s.

      The internet has really changed the way any of us can live. It’s incredible.

  20. I could not agree more with the premise of this article…I was 27 when I started out to do my own thing with my partners. If I was smarter and more business savvy I would not have done it. Two years in things were close to a disaster, losing money, working 110 hours a week, customers yelling. I was too stubborn to quit and go back to my cushy corporate job and admit failure. Well it will have been 16 years this December, and without a doubt it was the best worst decision I ever made to do my own thing. I’m FI, zero debt, great staff, work 40ish hours a week, all at a time when my friends are getting promoted to big time jobs and now they are going through the hell and stress while I’m able to wind down and work at a pace I want. Take risks young people!

    1. This is great to hear. Yes, take risks young folks!

      I wonder what is the success rate of your peers who also started businesses at 27 or in their 20s? Any idea at least anecdotally how many struck gold and how many went broke or back to work?

      1. I was the only one that I know of that took the leap of faith…I got made fun of a lot when I was at work at 6AM on a Saturday after going out to the bar with all my buddies. The “safety” of working for a big company is too much for most to let go of. The area my home is in is probably 85% small business owners & most of them are foreigners who came here with nothing and worked their tails off building their own business. For some reason, my generation and those with similar backgrounds for the most part were very risk adverse.

  21. Hey Sam,

    You need to get out of your comfort zone- the energy will come with that.

    Do a long juice fast, like the one I did- you can use the coach at the website (his name is Dennis and I personally recommend him).

    Once you go through that you will realize: it’s not very hard at all, you will have way more energy and be in better health, you will probably be ready to try new ventures… for example when I was doing it I ended up writing this song that is now available on Itunes (all proceeds are pledged to a local charity here). That’s me singing on it, as well as doing all the instruments. And this is while I am keeping up a full time job and helping to raise a newborn… we all have way more energy then we think…



  22. I’m interested in the “getting into Wall St.” post!

    I found this post particularly motivating. As a 20-something with an idea for a business, I keep debating back-and-forth about the merits of when to go after my dream. It seems the advice from “saltier veterans,” as you say, is always to go for dreams when you’re younger. Hmmm, perhaps I have some thinking to do.

    1. Oki doki. Let me see if I can put a Wall St. post together sometime before this year.

      Going after your dreams or taking a risk in entrepreneurship is easier at two point: when you are young and have nothing, or when you are rich and don’t need the money. Anything in between is very difficult. Life just gets in the way.

  23. Hi Sam,
    I’m in my mid-30s and together with my husband earn enough to afford to live in Los Angeles. Although I don’t have any complaints about my job, I do wish I was at home with my toddler instead of the day job. I do regret not maxing out my 401k and contributing to an IRA when I was younger. Now, I always think about perhaps starting an online business of my own so I can have more control of my time. It’s very scary though. We depend on the stable income with 2 kids.
    Ok, you did say to let you know of any typos, please check the first sentence of the very last paragraph, I think a couple words are missing.

    1. Creating a is much easier than you think. You can do it in an hour by registering the URL on GoDaddy and connecting it to your account for example. Give it a go! Lots of tutorials online to do so.

      Thanks for catching the typo! I love it and appreciate it. Missed “even though you know you should”

  24. Frugal Sage

    I enjoy posts like these, as it gives insight into how well this site does.

    I’ve only just started mine, and I have no intentions to monetize it at this point as it is more of a hobby than anything else. Perhaps my opinion will change over time, I am not sure. If it does I’ll make sure I sign up.

    I do agree that it’s much easier to remain focused on a task when you are younger, you have limitless ability to spend hours working on something. As you get older your friends and partners just start eating up a lot more of your available time.

    I suppose if the worst problem you have is being too lazy to change from being well off to super rich than, its a pretty good problem to have. :)

    Good luck with your endeavors with building the network.

    1. Thanks. Have fun with your site for the first year or two. And slowly consider monetization, but don’t focus on it b/c it will get you down since its peanuts in the beginning.

      I’m sure if you keep it up for 3-5 years you will do great.

  25. Work out. Eat healthy. Have he energy of a 20 year old again. All I’m hearing is a excuse !

  26. I think being hungry is one great reason to start young. Another reason is that you don’t have much to lose. I have to admit that fear is a big reason that I’ve held back from starting a business I’m interested in, but now I have a family to consider as part of my decisions that has only made me even more uncertain. But I also think there’s something to having some experience, knowing what you like and don’t like, and using that as a springboard to starting something of your own. So there’s a little give and take.

    With regards to where you are now, it seems like maybe money doesn’t need to be the primary motivator anymore. I wouldn’t lament the fact that it doesn’t excite you. That gives you a lot of freedom to explore other potential motivators. There’s a whole world out there to reach for beyond more money and you’re in a pretty unique position to be able to explore it. I’d love to see where you can go with it.

    1. It’s definitely a little bit of give or take Matt. I would say the best is starting a biz before 25 and being very open to learning. Get a mentor who will guide you. Enthusiasm and energy is priceless and POWERFUL.

      Money becomes very bland after a while. It’s more about seeing what one can do with their own two hands.

      It’s fun to think that when one types “Yakezie” in a search engine, 150,000 entries show up when before 2009, none existed.

  27. Hi Sam,

    I believe anybody has moments like you have. It is either regrets for missing something in the process of focusing on your “most important” goal or the regrets of not trying something. This is just life. I like that you realize that maybe one day you will “chuckle” later in life reading your posts.

    At any age there will be parts that you will miss if you focus heavily on financial ,material task.

    There is a part in life that has very little to do with money.

    1. When I was a kid, I WISH I had a camera. But I had no money and my parents never bought me one. I should have asked. I love looking at old pictures growing up b/c our bodies and minds change so much.

      Kids nowadays are lucky. When they are 60, they will see a perfect resolution picture or video of themselves as kids as if it was yesterday.

      A large part of why I write (and add pictures from my travels) is for this reason. So when I’m 60, 70, 80, dying… I’ll revisit what on earth I was up to in my 30s and hopefully 40s… b/c I may not remember.

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