Should you give kids money to start a company?

I remember the first time I read in the Wall St. Journal that it’s becoming common for parents to buy their kid a franchise so they don’t have to go through the trauma of looking for a  job.  And, for that matter, the kids don’t have to go through the trauma of entrepreneurship either.

I remember the first time I worked for myself. I was playing professional volleyball and I knew I needed a media kit to be able to send to potential sponsors. But I didn’t even have money for toilet paper, let alone putting together a media kit.

At that point, I had spent three years practicing seven or eight hours on the beach, and then lifting weights and sprinting after that. I had traveled from Chicago to Los Angeles to get to the best partners to play with. I wasn’t going to give up just because I ran out of money.

So I sold jewelry my family had given me. I didn’t know much about selling stuff like that. I sold my grandma’s pearls instead of the clunky gold necklace I got for graduation. The market was better for gold. But I knew nothing about how a pawn shop works. I thought I was actually selling something.

(Today, there’s a huge industry devoted to giving great prices for unwanted jewelry. Like, if only I had been so efficient as to get engaged and call off the wedding: I could have sold the engagement ring at Worthy. Great prices there.)

Anyway, I sold my jewelry and got a terrible price for it and had no idea I could go back to the pawn shop and buy things back. But really, it didn’t matter. Because I’d never have put the money toward buying the jewelry back anyway. What I really wanted was sponsors for my beach volleyball career, and you know what? I got them.

Kids dream big when they’re just starting out. It’s great to have big dreams if they are realistic, and it’s disappointing if they’re delusional. But the crux of life is learning to evaluate your own dreams. Which requires, of course, failing.

Forcing kids to spend their own money to start a business insures that they’ll focus and work hard to find out quickly whether  running a business is right for them. So much of learning from mistakes is making sure you don’t dawdle while making that mistake. Quick failures lead to more quick failures which leads to lots of learning in a short amount of time.

Failure works only if the parents can stomach it.

I never told my parents I sold the jewelry, but my mom did ask me a few times why I wasn’t wearing the pearls, because “they’d look great with that dress.”

By now my parents have figured out where the jewelry went. But you know what? I got more out of learning to run my own sports sponsorship business than I would have ever gotten from wearing the jewelry.

It turned out that while I could never get higher than 25th seat at US nationals, I was one of the five most sponsored players on the women’s tour. Which taught me that I am better at business than sports.

But even if I had sold the jewelry to fund business ideas that failed, I don’t think I’d regret doing it. I went on to start four companies, and while launching each one I ended up, at one point or another, having to put more money into the company than I should have.

I learned to bet big on myself when no one gave me money for my first business venture. And I’m here to tell you that knowing how to bet big on yourself is the best business plan, the best career move, and the best safety net I’ve ever had in my adult life.

So don’t give your kids money to start a company. Give your kids a free bedroom to start it in. And a free support system to rely on when the emotional challenges of work get to be too much. Because you can’t buy that type of support, and that’s an important lesson as well.

Epilogue: When I finally started making money with my startups, I bought french chandeliers for my house. They’re like jewelry for homes, and I like knowing I’m stable enough financially that I won’t ever have to pawn them.

29 replies
  1. Susan
    Susan says:

    I love this. We do have some education money set aside for our daughter, but my first choice is for her to either open a business/start freelancing or learn a trade and find an apprenticeship for it. I always wanted to try plumbing, but it felt so controversial to even consider when I was a 23 year old woman with a college degree.

    Anyway, I’m all for my daughter learning to make her own money as early as possible whether through something simple like selling stuff, tutoring or washing cars – or something bigger. Whatever. I just want her to know she’s in control of her earnings. My husband and I created our own jobs – I hope she’ll want to do the same.

    Self-employment is the only job security there is.

  2. Joy
    Joy says:

    nice, my sons got a job walking the neighbors dogs for a dollar a day each. It’s a good start, and they have never forgotten, and they love getting their ‘paycheck’ on Saturday.

  3. AP
    AP says:

    This is timely since my son has been asking for camtasia so he can make better videos for his youtube channel. He has some birthday money… We’ll see how badly he wants camtasia…

    • Mark W.
      Mark W. says:

      I have a free alternative to using Camtasia software for making better videos that may interest your son. The name of the software is VLC by the VideoLAN organization – “A project and a non-profit organization, composed of volunteers, developing and promoting free, open-source multimedia solutions.” It’s great software that I’ve only used to a limited extent but plan to use more since recently purchasing an audio media server which plays Internet radio and accesses audio files on a local network. It is open source software with a vibrant community that runs on many different operating system platforms. It is best known as a multimedia player. However as this article ( ) says in bullet #2. Playback your Desktop – “if you’re a home user just looking to record your desktop to share on Youtube then you’ll enjoy the screen recording function VLC offers” . If your son was planning to use Camtasia as described above, he can save money, make videos to share on YouTube, and learn with this community online.

  4. karelys
    karelys says:

    I love this post so much. Not one word is wasted.

    I was just talking to Chris about this yesterday. My brother still lives at home and has a big gap between his income and financial responsibility so I constantly bother him about starting a business because if all else fails it’s not like he’ll be homeless.

    Our parents never provided solid guidance to be successful in business or career. But they have always provided support and a safe place. Which at this point I feel goes further than anything else you can give your children or whoever you love.

    • Linda
      Linda says:

      I would have appreciated solid guidance. Could have saved me years of school and more years of jobs going nowhere. I found my way….slowly and with no help from family. They still disparage my line of work even though I bring 6 figures and help thousands of people in the process.

      If your brother had been guided, he might not still be living at home.

      Not sure I agree with the free bedroom for life arrangement as it leads to men playing video games endlessly.

      The question I have is how to motivate youth to be interested in entrepreneurship, professional job, or any path that is upwardly mobile.

      • Penelope Trunk
        Penelope Trunk says:

        Let’s challenge “upwardly mobile” as a goal. Like, upward from what? Why do things need to go up? I think fulfilling is more important. Teaching kids to have fulfillment as a goal is what’s important, I think. But it’s counter-intuitive to most kids because schools can’t teach fulfillment, so they teach that if you follow their rules you will somehow win a contest of upwardliness or something.


        • Commenter
          Commenter says:

          Upwards to the point their kids can hock gift jewelry to fund a business endeavor, maybe?

          Fulfillment is super, and easier to concentrate on with a full belly.

          The phenomenon of class polarization has been apparent to me in the last few decades. The lower middle class world I was born into and aspired to remain in dried up. The upper middle class world (into which you were born, and I climbed) became more comfortable, more closed, more hermetic.

          The difference in rhetoric between an upper-class education (which I’m giving my kids) and a mass education is striking: as you point out, mass education is very concerned with ambition and betterment – frequently in a way utterly divorced from reality. An upper class education talks first and foremost about the child’s happiness and fulfillment, not tests and stats. An upper class preschool can take the kids to play in the woods all day, where a lower class preschool will soak them in the anxiety of worksheets.

          What remains as a question for me is whether this attitude is necessarily a privilege restricted to the well-off. Wandering in search of ones true self can be a period of adventure and travel for the well-financed young, or a missed period of opportunity leading to a lifetime in restaurant work for the poor kid.

          Perhaps one answer is that addressing fulfillment early in the homeschooled child of modest means can leave him more prepared to strike when the iron is hot as a young adult.

          • Karelys
            Karelys says:

            I’ve pondered this a lot too Commenter.

            I was so stressed out as a child because of the constant “we have no money” talk.

            It’s very different to define middle or lower class nowadays because of education and information.

            We have no idea where we stand (Chris and I). We’re totally poor sometimes and sometimes we have a wave of money. But we’re never homeless. We have two houses in fact. Which sometimes feels like never having a home and it can be sad but it can be exhilarating too because now I feel like if we get the itch we can pack up and go anywhere we want.

            Materially we don’t have much. We just bought new cars and that makes me feel so much safer than if we had a nice house. Because with a nice car you can move and go anywhere for a job without worrying about whether it’ll start or not in the morning. We don’t own valuables but our brains are hungry and constantly curious and our attitudes can take down a lion. Not because we were born or guided to be this way. In fact, playing it safe was the word of the month every month from his family. For me it was, move across the country and into a different country if that’s what it takes for your family to have a shot at a good life.

            Moving to the US was akin to shooting for the Ivy League.

            I can see us living anywhere in the world and making it. We have enough education to know how to educate ourselves better. We are curious enough to know how to make the basics workout and improve them. We have enough creativity to make living poor feel fun and safe and sustainable rather than trapped and hungry.

            So I don’t really know what the classes really are like anymore. Other than the super wealthy. When you’re there it doesn’t matter if your education sucks or if you can’t think creatively. You can just exist and your wealth is so solid that it would take actual effort to make you poor.

        • Linda
          Linda says:

          My definition of upwardly mobile is 1) able to feed one’s self and family without debt, and ideally 2) able to maintain the lifestyle they themselves enjoy and seek to continue. I want my kids off the parent dole asap, whether or not they find their work fulfilling. I don’t want them endlessly seeking fulfillment on my dime….it’s not good for them or for me. That said, of course it’s optimal to both be fulfilled and to pay the bills.

          I am cutting way back on what I will spend on my 15 year old…I expect him to pay for his clothes and personal travel, for example, because I want to encourage his motivation to work. And he’s able to work so why postpone it?

      • karelys
        karelys says:

        I would have too. But the thing is, role models are out there.
        If you look you find. I think that’s the rough translation of a Spanish proverb, “el que busca encuentra.”

        I think I was staying true to my personality by following rules and striving within a system that didn’t fit right to my needs and abilities. But it was a given that eventually I’d deviate from the norm and seek something different. That’s just what I am.

        The thing I see is that guidance or not (from parents mostly) we won’t follow or appreciate the wisdom if we’re not open to it.

        My dad used to tell me to not “waste” my best years with my nose stuck in a book. I’d roll my eyes because I thought that was so …. primitive. I thought he wanted me to be a woman in a traditional sense (in the kitchen and pregnant, maybe? haha).

        Maybe his delivery wasn’t the best for communicating the heart of the message but he was right. He never thought too high of school. I thought he was just ignorant and uneducated. And here I am, all for unschooling. Not a huge advocate of college either. But I am a true believer in self-education. And so is he.

        He was a diamond mine in wisdom all along and I was just not ready to receive it. But once I started seeking an alternative path to what was offered to me everything clicked.

        • Commenter
          Commenter says:

          Karelys, usually in English we hew more tightly to the antiquated language we prefer in our bibles: “Seek, and ye shall find.”

          I think a more literal reference to Matthew 7:7 in Spanish (buscad y hallareis) would sound weird – like a priest or holy roller – in secular Mexican society where similar language seems normal in ours.

          I suppose that sort of language became unfashionable in Mexico around 1917.

          • Karelys
            Karelys says:

            Yes and no because Mexico tends to be very religious so even if you’re an atheist or right out try to be a heretic, you’re soaked in religious references.

            Commenter, you make me smile. You’re so smart and so good at communicating what you mean. Half the time I feel choppy when I try to explain what I mean.

            And I love the part that I still can’t figure out if you’re a man or a woman. I was so sure you were a man until one of your comments in the most recent career blog post. When you don’t comment we miss you. Don’t neglect us!

  5. Karelys
    Karelys says:

    ps. we have this idea that owning property to rent is a good way to make sure we’re not old and destitute despite how much work it takes in the immediate future.

    We dipped our toes in the pool by moving and renting out our home. Thanks to my eclectic background I made sure we did everything right and legally to protect ourselves and our tenant. Said tenant started a fire by being neglectful. This was right after having spent almost a week hospitalized and having emergency surgery. Which was right after my job ended.

    What I love about the fire is that it burned away fears, insecurity, and bad attitudes. We decided to fix it ourselves rather than use the insurance for a myriad of reasons. The process has been long and a week of nonstop work while I breastfeed my 2 month old. But you know what, instead of deterring me from owning property and starting a business I realize how strong we are and how skilled we are to handle difficult situations and keep a cool head while thinking long term. We are able to rein our emotions and make sure we don’t indulge in unproductive thoughts and feelings.

    But we wouldn’t be able to do it so well without our family support. I’m impressed by the adults we have become but I’m more impressed by the relentless love and help that our family provides.

    So I’m confident we can make it in business or demanding careers.

  6. Rachel C.
    Rachel C. says:

    Interesting post. I can see the value of teaching them to bootstrap, but you’ve also created companies that required VC to operate at the level you want to. I think there could be some learning value in having kids “pitch” to the VC firm of mom and dad. Realistically, a lot of kids are going to have a capital problem starting out, so I could see a learning opportunity with either side.

    I just love the idea of my kids starting their own businesses young. I wish my parents had guided me in that direction. I have a serious fear of failure.

  7. Gena
    Gena says:

    A lot of good points in this post. Key for me is to keep watching my kids entrepreneurial ideas and encourage them as much as I can.

    I have a very different question though (feel free to point me to another post if you have already addressed this somewhere else).

    I am wondering what kinds of activities are important to put kids into? I recently heard an interview about how everyone emphasizes team sports but top universities look at sole activities where you really need to use your brain and survive (sailing and horse back riding). Very interested in recommendations.

    • Linda
      Linda says:

      Participation in team sports is a better predictor of success than GPA.

      For activities I try to let the child pursue their heart’s desire. For one son, who has been homeschooled since age 8, this is drama, singing, performance. For my older son, who was private schooled until age 14, it was all about sports after school and he got plenty of enrichment activities at school.

      Trying to impress college admissions offices does not factor at all in selecting after school activities. But I suppose Stanford’s admissions rate for homeschoolers did help me to decide to let my teen drop out of high school.

    • Karelys
      Karelys says:

      This is such a sweet comment.

      I now live in a single wide mobile home that is ugly outside and so cute inside. It blows my mind how big something so small can be if you arrange it properly. Like now, I have no idea what’s the point of more square footage.

      I think I shall hang awesome jewelry in my little house. And this is why:

      Recently I watched the movie “Seeking a Friend of the End of the World.”

      I bawled.

      That night we all slept in the same queen sized bed because I just couldn’t let go of my children and my husband.

      In the movie, one of the ladies wears all her super fancy stuff that she kept saving for a good occasion. It made me so sad. I don’t want to wait to have a super nice house to hang a chandelier in. I think I’ll make my own and hang it in this house so I can smile every time I wake up ridiculously early even though I am so tired. I’ll sit on my couch and curl up drinking stupidly strong coffee and starting at the pretty chandelier.

      It’ll also remind myself to make decisions with my loves in mind like if tomorrow is the end of the world but also like we have a little longer to live.

      • Mark W.
        Mark W. says:

        Karelys, I really like this comment. You know the phrase – A house is not a home? Which is to say, you can have a fancy house with granite countertops and exquisite cabinets in the kitchen and bath, hardwood and ceramic covered floors, three stall garage, etc. with very little additional unique and special additions to add character such as wall hangings, paintings, hand made furniture, etc. A home to me is totally customized for maximum comfort suited to your taste and liking however it may look within some boundaries. A home is a place you enjoy being in and says something about you. The idea of making a chandelier sounds like so much fun. I’m thinking of Penelope’s spoon chandelier. I would make a knife, fork, and spoon chandelier and hang it over the kitchen table. So when people come over for dinner, lunch, snack or whatever they could pick their own utensil with it at the ready from their seat at the table. Maybe also have something over the table which holds a few plates, glasses, and cups. Self serve. Something fun and unique yet practical. A one of a kind furnishing I own is a large redwood coffee table I have in the living room. Many years ago when I lived in So. CA, I took a trip to northern CA in my red Fiat X1/9 (a small & very under-powered sports car that was fun to drive). I stopped at a place that sold redwood tables. I picked out a rough cut slab with features and shape to my liking. I gave them money and my address to ship a table they built with legs attached. I did the final sanding and finishing with tung oil. I still really like that table and use it. And people that see it for the first time also really like it. So fashionable, practical, unique, and meaningful (not necessarily in that order) are some considerations for me.

          • Mark W.
            Mark W. says:

            My fun with friends varies by the friend and circumstances. I think some friends may avoid me for certain occasions. :) Maybe it goes with the territory of having fun or something. Life should be fun when possible but, of course, it’s not always possible. And to tie this thread to education, education should be fun too.

  8. Lisa
    Lisa says:

    Good post and I agree with everything. Here’s another reason you don’t want to hand your kids all of their job opportunities so they don’t have to experience the “trauma” of unemployment: their employees and coworkers will resent them.

  9. CSmith
    CSmith says:

    My 14 year old (unschooled) daughter has been teaching piano for a year now. She has four students and loves sharing her love and knowledge of the instrument. She also recently got a job at the library to supplement her income because she wants to save money to go to Europe next year. She realizes that teaching piano is not only much more income efficient but also much more time efficient but she wants to stick with her library job because she’s a social creature, loves books, and likes to help people .

    My daughter also devotes hours of practice each week to makeup design. This is something else she loves and has already done makeup for family and friends. She plans to put in the hours necessary to perfect her skills and turn it into a money generating/entrepreneurial endeavor.

    Our job has been to provide a loving home, support, encouragement, offer suggestions/ideas, be her thought partners. It’s been joy to see our daughter bloom into her own and see her pursuing what she loves. I am so happy we’ve had the presence of mind to get out of her way!

Comments are closed.