How to know if you’re an entrepreneur

Here’s an interview of me in Inc. magazine. John Warrilow did the interview. The topic was how to know if you’re an entrepreneur. I basically said that you know you’re an entrepreneur if you are crazy, in a manic way, and you are willing to risk the health of your family and have no chance of a stable income, ever.

Then John sent his book to me. It’s called Built to Sell. It turns out that John did a startup and he sold it, and his book is, basically, how to be so smart about doing a startup that you are aiming for a reasonable, not-pie-in-the-sky exit from day one.

I spend a lot of time talking about how startup life is completely crazy, and the founders are crazy for choosing it. But in fact, the lower-stakes, lower-risk entrepreneurship, where, instead of having investors, you use your own time and energy to make money on the side while you are doing other things – that’s a great way to structure a life.

Ramit Sethi has great advice on how to do this. Its called Earn $1K On the Side. And now I bet a ton of you are going to sign up for his program, and I should have negotiated beforehand to get a cut of whatever he earns from this post. But I am stuck thinking about insanely risky businesses with high reward and so I forget to do things like earn $300 when it’s just sitting there.

Okay. So, anyway, I’ve been thinking that everyone can be the type of person who tries stuff on the side, because the process is really learning about yourself and what you have that the world values (like Craig did here). The Farmer found me because he was researching about entrepreneurship; farming is an incredibly low-margin business, so farmers have to be great entrepreneurs in order to stay solvent.

The Farmer showed my eight-year-old how to feed a baby calf for a year so that he could sell the calf at market. My son earned $400 for that calf at a cattle auction, and I swear, we watched my son’s self-confidence grow right there, in front of our eyes as he collected his check from the auctioneer.

My five-year-old asked why he doesn’t have a calf. The Farmer suggested that since the five-year-old’s job is to collect eggs every evening, he could start and egg-selling business. Besides, my youngest son’s talents are probably less on the animal husbandry side and more on the sales side.

He caught people in the school parking lot and asked if they wanted to buy eggs. People asked questions: How much, how are the chickens raised, what color are the eggs. My son loved knowing the answers.

Someone asked him what he’s going to do with the money he earns.

My son thought about it. Then he said, “I guess I’ll build a hot tub.”


He organized each carton so there were many different colored eggs.

I told him to be very careful during the egg delivery because he won’t be able to make as many sales if he breaks a lot of eggs. He took the advice very seriously:

He got so good at selling eggs, that one day, he had a friend over and an egg order came in. My son told his friend that if he helps collect the eggs and deliver them, they’ll earn $4 and the friend can have half the money. The friend said yes, they put on their superhero capes, and they were off to the chicken barn.

So, after only a few weeks in the egg business, my son discovered what I think are the best parts of entrepreneurship: Building friendships, having fun, and taking joy in each small success. Watching my son makes me really believe that everyone can be an entrepreneur if the expectations for huge payout are small and the expectations of the joys of self-discovery are huge.

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  1. Jonathan Vaudreuil
    Jonathan Vaudreuil says:

    You nailed it with your comment on the best parts of entrepreneurship. I’ve done more interesting things and met some of the coolest people when I was at a start-up and now that I’m trying to do my own thing. Nothing like it in a regular job. If anyone has the inkling to try it, or join a start-up, do it. You will gain something magical from the experience.

    Of course, there ARE perks to a job at a more stable company.

    BTW, Ramit’s Earn1K is a fantastic program. I don’t make any money if you sign up, either.

  2. Larie
    Larie says:

    Good evening! I really enjoyed visiting your site. The picture of the eggs in the safety belt is my favorite!


  3. Amy parmenter
    Amy parmenter says:

    I like the idea of making any transition ‘on the side’. It gives greater opportunity for exploring options because desperation and fear do not play as big a part in decision making. Been there. Done that. Doing it again right now. Thx p.

    Ps Love the photo. Pure joy. Thx for sharing.

    Amy parmenter
    The parmfarm

  4. Irving Podolsky
    Irving Podolsky says:

    “…if the expectations for huge payout are small and the expectations of the joys of self-discovery are huge.”

    THAT’S IT!

    In the past, my side projects were certainly joyous and gave me huge growth. But then I set about trying to “sell” my widgets with satisfaction leveraged against only one outcome: a big leap of income and professional credibility. Naturally, the joy got worried to death which killed my enthusiasm for continuing. So now I’ve changed my attitude. I lowered my expectations for quantum leaps and continue the “marketing” tasks as part of the creative process, rather than a chore that has to be done to do the next “arty” thing.


  5. Ash
    Ash says:

    I love reading the stories about your sons, and seeing those cute pictures. I have to ask this though – aren’t you worried about your children’s privacy etc?

    • Penelope Trunk
      Penelope Trunk says:

      I actually think about the issue of the kids’ privacy a lot. In fact, the best egg-selling photos were of my son and his friend going door-to-door hold eggs and wearing super-hero costumes. But their matching capes have their names on them in big bold letters, so I didn’t post the photos.


  6. Marc Roston
    Marc Roston says:

    So, I’m concerned you’re teaching the boys (in an internet start-up entrepreneur sort of way!) that all that matters is top line volumes! They need to know what it costs to produce an egg, or what it costs to produce a one year old calf. That way, they can decide whether to invest in another chicken to lay more eggs, another cow to produce more calves…or another crazy risky start-up!

    • Penelope Trunk
      Penelope Trunk says:

      People always talk about how this blog is so intimate. But now, we go to a new level of intimacy, as my brother and I hold a typically private conversation in the comments section of my blog.

      So, Marc. You will be happy to hear that we actually went into great depth to explain the economics at an eight-year-old level.

      The Farmer has about 100 cows that have babies each spring. Sometimes, there is a mom who can’t take care of a baby. That baby is called a bottle calf because someone has to feed it by hand.

      The Farmer would normally make money from the calf. So he gave the calf to our son with the understanding that if our son sold it, our son would owe the farmer $100 for the calf. The Farmer also helped our son figure out how much the milk replacement formula cost. Our son immediately realized that he’d make more money if he fed less milk, so we explained that the calf would not grow as much, so he would not earn as much money if he did not put money into the calf.

      In the end, here’s the breakdown from the $400 check:

      $100 for the calf
      $100 for the feed
      $15 commission on the auction

      My son took the earnings and bought a pregnant goat. The goat had a girl, so he has doubled his money. Now he is figuring out how much hay costs.


  7. Rae Gross
    Rae Gross says:

    This was a great post! I have been trying to tell this to my boyfriend for a long time. I always make small bits on the side consulting on social media, and I turn down stuff that would require a bigger time commitment than what I have because I am not ready to start out on my own consulting firm. I like the little pay offs (saving for a house). Thanks for illustrating this so well :)

  8. Doug
    Doug says:

    One of your best posts. If the reasons are right and the expectations reasonable each of us has the spark inside us to create something special. We all just need encouragement and the faith to believe we have genius inside waiting to be unleashed.

    Great thoughts.

  9. Lene Johansen
    Lene Johansen says:

    This is a great personal story! I have had the fortune/challenge of helping a few kids that have not been taught about small achievements until they were in their late teens and ended up around me. It is sad that so many kids are not taught about small achievements and the great personal benefits those have. The lesson is finally sinking into my step daughter, who I found after three weeks of investigative reporting. Her mom had ran away with her 12 years earlier, and her dad got so sad around her birthday every year, I could not watch someone I loved be that sad. I found her, she has lived with us ever since, and she is getting it slowly. Now I just have to get her to trust her instincts, because she still doesn’t dare to try and fail, because that hurts too much. Not trying and failing hurts less. But she is getting there, slowly, and she is turning into a beautiful, smart woman. She is starting to catch up after all the years of no parenting. I’d love your advice, if you have suggestions on what I should read and implement to help her find her inner cajones. She has them, she just doesn’t dare to apply them to the big stuff yet. Thanks for being you.

  10. Mark W.
    Mark W. says:

    Hmm … how about creating some value-added products from those eggs such as egg salad sandwiches, hard boiled eggs, etc.?

  11. chris Keller
    chris Keller says:

    This all sounds so rosy and straightforward. What about the 2-year rockiness that you always hear about with start-ups/small business ventures?

    Shouldn’t we all learn that things may not run completely smoothly? That things may be slow/tenuous at first?

    • Penelope Trunk
      Penelope Trunk says:

      Well, that’s my whole point of the post, really. That if you have modest aims — like, for my son’s egg business, it’s about $20/month — then you will have modest risk. For my son, the risk is very low, and he’s been having a great time.

      If you have huge aims — like, for my company, Brazen Careerist, we have committed to investors that we will exit for upwards of $15 million — then there is huge risk, and lots of tumult trying to get to that end.

      This post is a toast to the calmness of taking joy in small successes.


      • chris Keller
        chris Keller says:

        Last line–post is a toast: internal rhyme, truly poetic.
        Change “taking” to a word that starts with “s” (“seeing” or “seeking”), and you will have alliteration, as well. More poetry!

  12. Mateo
    Mateo says:

    I am a true believer of working for yourself. Being raised on a farm myself, I understand teaching younger people entrepreneurship. I see many young farmers promoting there products but it’s not only farms there many different businesses a person can start-up.

  13. Maria Killam
    Maria Killam says:

    I just loved the eggs in a seatbelt photo, OMG that was so adorable, I can just imagine a 5 year old doing that. Love, love, love your blog Penelope!

  14. Rachel
    Rachel says:

    Finally! A post I like. You are a real wierdo Penelope Trunk, but this makes me almost like you again too.

  15. Kay Lorraine
    Kay Lorraine says:

    I know that everyone is saying that they like the eggs in the seat belt picture best, but my favorite is the variety of eggs in the carton. He has arranged them beautifully. I would definately buy eggs from this kid. Unfortunately, I live in Hawaii so the shipping costs would be a bitch. But my heart is with him. The Farmer seems to be very good for your kids. Congratulations!

  16. Thomas
    Thomas says:

    Penelope – your ‘learn by doing’ approach with your kids is so cool. And retro. I imagien this is how children learned life skills before public school came along and got them focused on shoes and co-branding before they know the simple joys of completing real life tasks. Kudos to Farmer for passing the buck, literally.

    I think the word ‘entrepreneurship’ scares a lot of people because they think of jazzy Silicon Vally types selling esoteric software things, people who talk about ‘valuation’ and capex and stuff. In reality, small business culture has always been integral to the American way and the primary drive for this has been simple – independence, pride of ownership, self sufficiency. These things have been displaced by the ‘mass produced’ version of entrepreneurship, which certainly has its place, but now the basisc stuff is making one hellova come back becasue it is now very east to find and even create niche markets for goods and services through the explosion of communication tech.

    I remember reading about Ghandi and getting all excited about his ‘home-spun’ populism for Indian cottage industries against industrialization. Today, we ahve more opportunity than ever to rebell against the status quo by going into business for ourselves. A lot depends on circumstance, though, and character. Making an extra buck on the side is a good way to start as psychologically, people feel safer (if it doesn’t work, it was fun and no harm done)but many people are now discovering the ‘be your own boss’ monkey in themselves becasue the economy sucks and you gotta eat and pay rent. This has higher stakes, but the motivation is more intense (I gotta make this work before 5:30 on the 5th of the month or I’m screwed) and through little successes like selling a flat of eggs or getting your first client to agree to your terms, you gain confidence and self knowldge that no corporate or educational system can teach you.

    Go go go.


    • Angela
      Angela says:

      “… this is how children learned life skills before public school came along and got them focused on shoes and co-branding before they know the simple joys of completing real life tasks.”

      Public schools did this to kids? What about parents? The media? Society? Give me a break, and please stop blaming public education for everything.

      • Melanie
        Melanie says:

        I didn’t hear that in his reference to public schools. It’s pretty hard to deny that public schools have been a huge social experiment, and that the process has drastically changed childhood experience. I’m not saying public school is bad. But each generation has changed in ways that are multiplying effect and one of those ways is we have walked farther away from each person seeing what we would now call micro-business and engaging in small experiments with earning money more directly than getting a job.

        Yes, the people who have an ax to grind with the public school system often do that for politically driven idealogical reasons. But that is very different from assessing the situation and seeing how it has changed our relationship to various experiences.

  17. Peter
    Peter says:

    Your kids are cool. Sounds like they’re going to be very successful someday, since they’ve already had a good start.

  18. Clara
    Clara says:

    You once said how gaps in your cv and life in general should be best put to use by trying new things, learning about yourself and learning to better yourself. Or you said something like that and then I extrapolated.

    I think trying things on the side is a key ingredient to growth and discovering your different potentials. Thats the way I started my personal training business: I love fitness, I love talking to people and motivating them about health and I love seeing people achieve their goals with my coaching. Huge leap from law and women’s rights, but no matter. It works.
    Great post. The pictures are stellar.

  19. Helen
    Helen says:

    Wow,this is exactly what I’m doing right now too. I’ve started a business on the side while keeping a full time job. My intention is to quit the job in September, giving myself this time to see if I can make a living out of the business. The business has given me that joy in my life back and now I feel that no matter how much or how little I will make from it, I am willing to jump in 100 percent and make any sacrifice necessary to live my life in this joyful way!

  20. Mike
    Mike says:

    Great post. I would add that we lose sight of what is when we define entrepreneurship as necessarily being about making money. It really is about taking the risk of putting yourself out in the world, whether you’re doing it for income or otherwise.

  21. Melissa Breau
    Melissa Breau says:

    PT, just wanted to say that I loved this post.

    I’ve recently connected with a few women who are focusing on raising kids who will learn about being entrepreneurs; they encourage their kids to start their own businesses and understand the things involved. “Raising CEOs”

  22. Erin
    Erin says:

    Awww, cute picture!~ I might have to look into this “make money on the side stuff.” I’ve always wanted to try something but I don’t know what to try. I think first I need to have some free time.

  23. Jens Fiederer
    Jens Fiederer says:

    I rarely comment unless I have something either pertinent or amusing to say, but this time I just loved the post so much I had to comment without anything to really contribute.

  24. lynne whiteside
    lynne whiteside says:

    to learn that nothing comes to you as ‘fast’ and ‘immediate’ as you would like is a Big lesson for kids who want most things right Now. You’ve been a great Mom to teach your kids some fundamental lessons of life.

  25. Beth Jones
    Beth Jones says:

    This was an excellent post. I loved hearing about your kids making money like this and love the pics with it. The eggs in the seat belt pic is hilarious and the last pic is such a great, happy pic. I loved what you said about the best parts of entrepreneurship – so true! Thanks for posting this.

  26. Ilana
    Ilana says:

    I really like this post. I read your blog regularly because it is always interesting but the connection to business lessons is often a little loose. This one tells a nice story and connects the dots.

  27. Harriet May
    Harriet May says:

    I’m kind of jealous of your kids and the stuff they get to do at five and eight. But I’m glad that at least I have your blog to read, because I learn so much, and not just about the existence of cervical mucus either. I never thought I wanted to start a company; I didn’t think I was built for it. But eight months ago I didn’t know what I wanted to do with myself even in the short term, and now I have so many ideas and goals. Like, I have that idea for a company and I really think it’s a good one, so now it’s just a question of time and resources. And also I’m going to meet with a graphic design instructor at the local community college because that is a skill I could use if I did start a business, and in my current position, and for fun. So although I will pay for the education, I will make myself more valuable, hopefully expand my network and have a new experience. I’m really excited. I’m also thinking that maybe I should do an MBA at Queens, because it’s a beautiful campus and why not?

  28. Denys Yeo
    Denys Yeo says:

    Hi Penelope, your story about your boys learning experience made me think of an amusing television ad we have had here in New Zealand where a farmer gives his son a lamb (baby sheep! – and we have a lot in NZ) to fatten and sell – boy works out costs, fattens lamb, sells it, makes money on the deal but at the last minute can’t let it go to the meat works – lamb is saved – races off sheep truck, races past boy (with no sign of gratitude) and heads for the nearest ram (randy male sheep). Ad ends with boy selling wool by roadside alongside a tethered and grumpy lamb! These stories all sound a bit like the real world to me – €“ and I think kids growing up on farms often have opportunities to learn about real world stuff long before kids in towns and cities. Good luck to them.

  29. rajpfj
    rajpfj says:

    It’s wonderful to see kids learning how to work, and how to earn smallish amounts of money. And understanding everything that will be involved.

    In the old days, boys had paper routes or a shoe-shine business. These days, what is there?

    But I need to make a correction:

    => They are not learning to be ENTRPRENEURS.

    => They are learning CAPITALISM. (The good kind. Not the greedy, cheating, self-serving, amoral kind.)

    Entrepreneurs do something new, something daring. Whereas raising a calf or goat, or raising chickens and selling eggs — those are usual and ordinary expressions of capitalism.

    It’s wonderful that by the time they become adults, they will have a real grasp of how money is made (and sometimes lost) and how much work it takes to make regular, ordinary money. And they may be immune to get-rich-quick schemes.

  30. Sunny Lam
    Sunny Lam says:

    Most entrepreneurs still end up being crazy if they start their own business.

    Of course, John’s more reasonable path makes sense.

    Some people say that if you’re going to start a business on the side that you want to be careful of its pitfalls :) (5 Tips for a Running a Part Time Business

    Unfortunately I never had any a real choice in the matter.

    In fact I co-founded a city farm a year or two back and had to leave because it was too much work for too little.


  31. Cynthia Kocialski
    Cynthia Kocialski says:

    I’ve worked with many entrepreneurs and I started 3 companies myself. Entrepreneurs are creators, they like to make something. When the job becomes routine, they feel unfulfilled and move onto the next creation.

    One thing I’ve noticed is that as the company grows, the personality of the people attracted to work at the company changes. In the early days, it’s the true start-up people, they all want to create, they are performance and results oriented, and they like to be involved in many aspects of the business. By the time a company gets to 100, the employees like to do what they are told, they like the security of having a set of tasks , they like the comfort of getting what they can get done without any pressure to perform. And this is where you see the early start-up leave because it’s fustrating. When the company gets to 300, the office politicians show up, employees focus more inward to compete with other employees instead of focusing on the outside market, bureacucracy sets in, and business improvements are incremental changes.

  32. Wenko
    Wenko says:

    you and the farmer are great examples for your kids. i wish all parents will follow in your footsteps. relationships are the real treasure and not money. good job and God bless!

  33. kate
    kate says:

    love the pics so much! so glad you’ve been posting more of them . . . they add such a deeper, rich aspect to your stories . . . (ps – would love to hear your take on the michigan and now possibly wisconsin gov’s financial takeover . . . )

  34. Rosa
    Rosa says:

    I recently discovered your blog and i find your opinions are very interesting, plus they’re often backed up by facts! excited to follow your posts as they’re continually written

  35. Kathy
    Kathy says:

    I know that your photos are not the point of your posts but I wanted to tell you how nice it was to see that wonderful smile from the farmer.

  36. Sean @ Steelage Man
    Sean @ Steelage Man says:

    Your Son already seems like a natural when it comes to business and it was very clever of him to put eggs of different colors in the carton. This is a great lesson for children in marketing and creating a niche product in such a saturated industry.

  37. Kevin Thomas - Songwriting Planet
    Kevin Thomas - Songwriting Planet says:

    This story makes me think of the way that I was raised. It seems that the education system in America is partially designed to strip the entrepreneurial spirit out of us so that there are slaves available for the work force. It is good to hear that the spirit is still alive with children in some places. Kind of gives me hope. Kevin

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