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The Simple Secrets of a $100 Business

About a year and half ago I took part in the first round of a new and interesting online project called the $100 Business Forum run by two of my favorite entrepreneurs/people, Chris Guillebeau and Pam Slim.

The idea was simple: Over 28 days we’d build the framework of a business that cost $100 or less to start. This is the course that became the catalyst for Riskology.co and the business I’ve built around it that now supports me.

The bad news is that this great starter program no longer exists. The good news is that today I’m announcing a new project that not only picks up where The $100 Business Forum left off, but also improves on the model.

More on that in a second. For now, let me explain the concept of a $100 business because the idea of starting something for so little money is foreign to most people.

What Does it Really Take to Start a Business?

To tell the truth, Riskology.co is actually the fourth business I’ve started for less than $100.

When I was in high school I started a very small landscaping service (ie. myself, a few tools, and one client) before going on to start another small-time business collecting hay for local farmers with a few of my friends.

In college, when I realized how well I knew the music scene in Portland and how close I was to several popular venues, I started another small business reselling (also read: scalping) concert tickets.

Side note: As you can see, you don’t necessarily need a unique and impressive talent to start a business. Just solving basic problems goes a long way.

None of these businesses made me a fortune, but that wasn’t the point. They were projects that cost almost nothing to start, could be run in my spare time, and paid my most important bills. More importantly, each of them could have been easily scaled up to full-time businesses if I wanted or needed to.

To start a successful business—one that makes money and doesn’t destroy your will to live—you don’t need funding, investors, employees, tons of equipment, or a 90-page business plan and a fancy suit. And even though I recommend it to most people, you don’t have to quit your day job.

 Instead, what you need are just three very important things:

  • A group of people that have a specific problem and are able and willing to pay to solve it.
  • A product or service that provides an adequate solution.
  • A simple way for people to give you money.

With these three things in place, you can start nearly any business in the world. And they all cost far less than $100 to acquire when approached with a little ingenuity.

Thinking Small – The Version 0.1 Launch

The problem with most business ideas are that they start out far too big.

You look at other established businesses and think you have to match their size from the beginning if you want to be able to compete. Or you’re afraid that if you don’t have an office with a fax machine and receptionist, that people won’t take you seriously. Or if you don’t have a million dollar website, you’ll never attract the customers you need to make it.

You dream really big and start to imagine everything your business ever could be if it was wildly successful. From day one, you get the idea in your head that you must launch your business fully developed—that you have to start with “version infinity.”

Unfortunately for many, this leads to mental defeat and an acute case of procrastination.

Instead, as Derek Sivers explains in his brilliant YouTube lecture, what you really need to do is launch version 0.1—the smallest viable business you possibly can. This is what will eventually grow into your big dream, but today it’s only a seed.

You cannot plant a 100-foot oak tree. You can only plant a seed and nurture it.

Knowledge is Not Enough

With the state of communication and the Internet today, I am supremely confident that anything you could ever want to learn can be learned rather cheaply and easily. The knowledge required to start a bootstrapped business is no longer a barrier to entry.

But knowledge is not enough. This becomes obvious when you look at problems like obesity in America. Even the least educated among us know exactly what we need to do to solve the problem. The answer is not difficult to find or understand. Yet, the problem (and people) grows larger every year.

What’s missing is action. If you leave execution out of the equation, the product will always be zero.

We all know how to start a $100 business, but few of us actually do it because the hard part is finding the motivation to execute.

Introducing The Bootstrapper Guild

Given the specific challenges around starting a small but meaningful and profitable business—loneliness, confusion, lack of truly useful resources—I’ve developed a program specifically for us.

It’s called The Bootstrapper Guild and it’s an online community for do-it-yourself entrepreneurs like us who understand that skillful execution is far more valuable than start-up capital.

The premise is simple: each month we’ll focus on one and only one strategy to creatively develop your business the bootstrapped way.

In addition to the monthly lessons and execution plans, there will be a community of like-minded entrepreneurs available 24/7 to bounce ideas off of, learn from, and form partnerships and masterminds with. An easy to navigate one-stop shop so to speak.

You bring the ambition; we’ll provide the guidance and accountability. Together, we’ll make business happen.

The Bootstrapper Guild will be opening soon, but only for a short time and to a small group of pioneer members.

If you’d like the opportunity to get in on the ground floor, drop your email in the form below and I’ll make sure you’re the first to know when the doors open.

Bootstrapper Guild Priority Notification List


I’ll never share your address with anyone.

After you’ve signed up, come back and answer this question in the comments:

What’s the #1 thing keeping you from starting the business that’s been kicking around in your head?

Myself and other Riskology.co readers will try to offer some help to get you on the right path.


Image by: Surat Lozowick

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What smart people are saying about this...

  1. I am a full time teacher – and love it- but when my first child was born I realized I needed to make a bit more money and started a resume writing service. It never progressed to more than a small hobby business.

    Last year I created Quality-Resumes.com but have yet to see it really take off. I think one reason is a reluctance to strong self promotion. (Ironic when what I do is help other self promote!)

    • Hey Steve,

      Like you said, it could be a self promotion thing. It could also be that your service isn’t specific enough yet to really catch on. Right now it looks like you offer resume services to anyone with a resume. What if you tried to be more specific and offered resume services to people *only* in a certain industry.

      That might seem at first like you’re limiting your opportunities (you are, intentionally), but it will also make your offer more attractive to a certain group of people. Once you gain momentum with that smaller crowd, you can parlay that into more work with a broader audience.

      • Steve and Tyler,

        I found this community though a guest post Tyler did on artofmanliness.com (my second favorite blog). They had a really good post today on getting off a “plateau” in your life. Look it up Steve. It might help you understand why you should push self promotion, and why failure is so valuable. I guess the short form is that if you don’t push, you can’t fail, and therefore you gain no growth/value.

  2. Procrastination brought on by fear of success! I know that even my photography can be bootstrapped (rental equipment) but I keep telling myself I need another camera, lens, more lighting equipment, etc before I can call myself “a professional.” People ask me for my website and business card all the time and I have to tell them it’s still under construction.

    • Aha! I suffered the same problems for a long time, James. The truth is, if you have a skill and you’re offering it in exchange for money, that makes you a professional. Getting comfortable with that idea can make all the difference for your own confidence.

      You don’t have to have the best gear or the greatest skills in the industry. You just have to be better than the people you’re trying to serve. :)

      • “You just have to be better than the people you’re trying to serve. ”

        This is one of the best pieces of advice I have read recently.. Very fresh and no doubt about the effectiveness :)

  3. A lack of focus – I have created a blog and have seen the traffic steadily increasing, but I have yet to offer a product or service on it. I have made some money from affiliate marketing, some from advertisements, drafted a children’s book and submitted it to an agent, have plans to start another site, etc. I keep putting a little effort into each idea and hoping one will just stick!

    • There’s nothing wrong with that approach, Karla. In fact, that’s how I got started with Riskology.co as well. And it sounds like you’re seeing gradual success which is, of course, a good sign.

      The key decision will then be, like you said, making the decision of which project will get your main focus. That is, only if you want to scale things up. If you just enjoy having lots of little projects that make a little here and there, there’s nothing wrong with that either.

  4. Like many others I am very ambitious and big dreams to may be one day come up with an idea that will be AWESOME!! :)

    For now I am focusing on my photography. The challenge has been to reach the target market.

    I also maintain a blog to reach out to people who I can share my life’s experiences with and help them to reach their goals. It is very generic. Again the challenge is to reach the target market.

    • Hi Dharmesh,

      You brought up a couple things, so let me address each one the best I can.

      1. Like Derek Sivers explains in his lecture series (linked in the article), an idea is only a multiplier. You have to match it with execution for it to really be worth anything. So, an average idea with hard work and good execution can yield a really great business. At the same time, an amazing idea with no follow through isn’t really worth anything.

      Basically, you don’t have to wait for the perfect idea to come to get started.

      2. Yes, finding that specific group of people you can help the most will, no doubt, speed progress. See my answer above to Steve (1st comment). That explains the idea.

      In the Bootstrapper Guild, we’ll definitely be covering exactly how to find the right market/audience in detail.

      • Thanks Tyler. I am looking forward to Bootstrapper Guild.

        I have read so many articles that say “define your target market”. I have done that. I know where I want to be and who I want to sell my photographs to. I don’t know where to find them :( Need some tips on that.

        Sometimes it happens that when someones says it loud you notice… I noticed this today..

        “So, an average idea with hard work and good execution can yield a really great business. At the same time, an amazing idea with no follow through isn’t really worth anything.”

        I hope to hear some ideas that I can collaborate with someone to bring it to fruition

  5. Hi, Tyler,
    This is an intriguing post. I’m currently working full-time (benefits) and part-time (freelance) as an editor. I would far prefer, however, to be in the alternative health field, working with clients to integrate western and alternative healthcare approaches in their lives. This is going to take awhile–I have a lot of training to get through, both traditional and not-so. I would love to be able to make this a viable business though, and the Bootstrapper Guild sounds like it could be a great step toward getting me there!

    • You bring up a good point. There are certain career tracks that, due to regulations, require some time to get into.

      However, even within those tracks, there are usually opportunities to get started in the field on your own without doing the things that require special certifications/degrees/etc.

      Finding a support type role that you can start in also establishes your foothold with your customers so that when you do get to where you *really* want to be, you have a business already built and can start offering more services.

      It’s all about figuring out how to get started very small. :)

      • Is there a local shop that retails Alt medicines? Perhaps you could ask for a 6 – 10 hour gig per week at minimum wage or as an intern for a bit. The advantage being that when there aren’t customers to serve, you could rifle the shelves for herbs and such that you’re not familiar with, maybe write down three per shift, then look them up at lunch during your day job. Also, as you get to know the old hands at the shop, and are studying for your Certifications, you’ll have tutors to whom you can say “This is my homework, what’s up with….?”

  6. Tyler – Can’t wait to learn more about the Bootstrapper’s Guild :)

    The number one thing on my radar right now is credit card debt. I have about $11,000 of it and I’ve committed to paying it off before I leave my day job to become self-employed again (hopefully in the next 5-11 months). It hasn’t prevented me from starting my business, but it is preventing me from fully committing to it.

    • Ah, yes. That can be a real ball-and-chain, can’t it!

      Like you said though, it hasn’t prevented you from starting your business, just from quitting your day job that’s helping you pay off the debt.

      It sounds like maybe the best opportunity for you, then, is to start to really focus on the “high level” stuff–the 80/20 tasks–that bring in the money so that you can increase the profit from the new biz without adding a lot more time to it and keeping the job that will help you pay off the debt faster.

      What’s the most profitable part of what you’re doing right now, and how can you scale that up in a way that doesn’t add too much to the schedule?

      • Haha – yep, ball and chain it is. What I wouldn’t give to go back and slap some sense into young college Sarah… :)

        As for profitability, the fastest way for me to make money is as a freelance web content writer, although I’m obviously limited in terms of the time I can invest in it. To compensate, I’ve been raising my rates and trying to pair with high end clients that can provide steady work at those rates.

        It’s definitely a start, although I’m also trying to build up a passive income portfolio that doesn’t require as much direct time investment as well.

  7. I have no shortage of ideas that I could potentially build businesses in. In fact, I keep a notebook with me all the time to outline ideas and write them down as things occur to me. I think there are 2 major things stopping me: 1. Time and 2. (as James said) Procrastination due to a fear of success. I think #2 is probably a corollary of feeling like I don’t have enough time. I don’t like to do things halfway, so I keep putting it off until I have “more time.” I know this is a slippery slope

    • Hey Steph,

      I can totally relate to that. What’s helped me a lot has been learning how to “chunk” which just means I figure out how to take bigger, time consuming tasks and break them down into small chunks. I try to make sure each chunk can be completed within 20 minutes so that I never have an excuse to procrastinate.

      The other thing that’s helped me a lot is the idea I borrow from the guys at 37 Signals (a software company) of “half, not half ass.” Always look for a way to cut out the least important parts of your work so that you have time to really excel at the most important.

      We’ll definitely be covering this kind of thing in detail in The Bootstapper Guild because it seems that lack of time is a very common issue.

    • Information overload is a great one, Dan. There is soooo much info about starting a small business out there. It can be easy to keep putting off the start of your business until you know “everything.” Unfortunately, everything is the one thing we can’t know.

      • Yes! So much information! So little time!

        The basic answer is to simply watch the money. Where is the #1 place that money will come from for you and how can you focus more time on really helping the people that have that money and want to give it to you.

        There are all kinds of things you *could* be doing to start/build your business, but until you’ve got a steady flow of money coming in, there isn’t a lot of sense in focusing on it.

        Does that make sense? Identify the highest leverage tasks, then do them and ignore everything else.

        Every topic/lesson in The Bootstrapper Guild will be based on this principle.

  8. Hey!
    The No 1 thing stopping me is that I don’t think I know how to market myself correctly. Fear of failing? Or, maybe just thinking everything has to be perfect. Although I know there is a need that I can fulfill.

    • Hey Jean. Do you already know exactly what need you can fulfill? Getting very clear on that really helps to remove the confusion around how to market your business. The more focused it gets, the easier it is to identify exactly who you should be talking to and how you should be talking to them.

    • Well that’s where we all start, isn’t it? :)

      One of the fastest ways to start a business when you literally have no idea what to do or how to do it is to:

      1) Pick out five people you know who have a problem in their lives/careers/etc. that you think you could fix.

      2) Offer the solution to each of them and see which ones are willing to pay for it.

      3) Refine and expand from there.

      Picking the right market to help (able and willing to pay) is really important, so we’ll really hit this concept hard.

  9. Hi Tyler-you’re an inspiration!

    Unlike Kdivasilver I am in the alternative health field and now want to leave. Before going in to this field I did many things to support my art making except for being professional about it. That is, I accepted the old saw that it’s impossible to make a living as an artist (so I did lots of other things). During the last few years, I have begun to resent my oriental medicine business and neglect it. My heart isn’t in it. I am now starting the business that’s been kicking around in my head, I have to. I am currently working on building a body of work. I do Asian brush & ink and on paper. Like Dharmesh I need to get a website up, facebook fan page and cards. I think I have some idea who my target audience is (animals/flowers are often my subject matter or prominent in a landscape). I guess my biggest hurdle so far has been confidence in my work and perfectionism and transitioning from a career that I trained for but that I no longer wish to be in.

    • I hear you on that, Eileen. Lack of confidence can be a real motivation killer, especially when you’re business is connected to something as personal as your art.

      When it comes to selling paintings, though, most people don’t buy on looks alone. Yes, you have to create work that “looks good” to people, but the artist’s personality plays a big role, also.

      A strong personality that your audience can connect with and relate to will go along way towards selling more art.

  10. I have a great idea I’ve recently started to work on, but I feel like there’s a few things getting in my way.

    Lack of knowledge of the tech needed to proceed. I’m working on this one with the free education online but feeling a little overwhelmed. Seems like a lot of the tools I try to use don’t work as advertised. I’m starting to feel like my idea will never take off because I don’t have the correct tools to make it work. Some would say to just make the tools, but I don’t currently have the time or skill.

    Not knowing what the revenue stream will be like. I have a few ideas on how to use my idea to make money, but I’m not sure if it will be enough to sustain the idea. Even if it can sustain the idea, I’d still like to have enough money to pay myself.

    A lack of time. I’m working a full time job to pay the bills. The idea will take a ton of other time. I’m not sure if I have the time to learn the tools I need to learn to get the idea rolling.

    Fear of other people. I could try to bring in some people to help me, but I don’t know that many people with the skills I need. I’m weary of strangers because I don’t want my idea stollen.

    I’m trying to break my idea down into smaller chunks, but it’s difficult. I know what I want to do, I just can’t figure out a way to do it.

    • That’s the challenge when you’re a DIY entreprenuer — you run into all kinds of hurdles: time, money, skills, etc. and getting past them can be quite a challenge.

      If you’re having problems with technology, is it because you’re trying to learn too many new tech things all at once? If so, what if you scaled things back a little bit and focused only on the most important piece. Then, once that’s figured out, you can move onto the next piece. It might feel like it takes longer, but it at least keeps you moving and focused on the most important pieces.

      As for the revenue, there’s a risk you take in starting any business, but there are also ways to test to see how viable your business project will be before you fully invest in it. Hint: I’ve done this in several different ways just leading up to launching this project. We’ll talk about all those kinds of things inside.

      And yes, it can be scary to share your ideas with other people, but remember what Dharmesh and I were talking about in the comments above:

      An idea, by itself, is not worth anything. It has to be paired with good execution to become valuable. As long as you’re focused on executing and improving, no one can steal your idea.

  11. Lack of heartfelt confidence.
    I have had 3 businesses, all art related, first one very successful, next 2 not so much. The failure and debt terrifies me and keeps me stuck. I am crawling out slowly, painting to make postcards and other products, hopefully for our National Parks. I can start with version 0.1, that is GREAT ADVICE!! One park at a time!

    • Are you trying to get your designs accepted by the park services for sale? If that’s what you want to do, you should definitely go after it, but you may be able to get up and running faster designing for consumers. There’s many fewer hurdles between you and actually selling your work.

      Good luck, Eileen!

  12. The fear that it will actually be a success and become bigger than me. I’m a jack of all trades but a master of none and I’m proud of that. What if this idea works and I have to focus on this one thing. I’d hate to abandon it should I become bored. I’m my own worst critic (obviously) and fans freak me out :/

    • Hi Kay. Fear of success, as I’m sure you’ve noticed, can be just as big of a problem as fear of failure.

      I don’t think you have to stop being a jack of all trades to run a successful business. You just have to understand where you *want* to spend your time the most and design a business that allows you to do that. And you only have to grow as much as you want to. You’re in control, so if you get to a level that you’re comfortable with, no one says you have to turn into a big giant company that zaps all your enthusiasm. You’re the boss!

      As for getting bored? That’s always a risk, right? But if you always work to push yourself a little bit into new territory and try new things, it’s pretty hard to get bored. And the beauty of creating something bigger than yourself is that if you ever do decide that you just don’t want to be a part of it anymore, you can sell it and move onto something else.

  13. The truth is the one thing that’s been stopping me is myself.

    I’ve got a business actually started, I teach photography, but I haven’t truly dedicated and put in the effort to begin building it.

    I’ve always fallen trap to what you illustrate in your post, this feeling that I have to have this fully developed plan/business/website/whatever.

    I really like the sound of this new project, I signed up for the priority notification and I’m looking forward to learning more about this!

    Great stuff Tyler. Thanks!

    • When you’re going it alone, you really can be your own worst enemy. It’s usually the feelings of overwhelm that get me. But if I remember to slow down for a second and focus on just the important, things tend to work out and I make bigger steps forward.

      Focus on “version 0.1.”

      • Tyler, I have 30 plus years of international business operations management experience. I’ll do my best to help with Bootstrap, but I think my problem is that I’m a bit of a weenie.

        Spyros’s case is an excellent example. Just from reading his comment, I can assure you that he doesn’t want anything to do with business, except as a foundation from which to teach.

        How do you tell people that their focus is 180 degress off, without raising hackels? For Spyros I’d recommend that he wanter down the street, find the 16 year old neighbor, slip them $40 to set up the website, while Spyros goes back to what he loves – teaching photography.

        Spyros uploads his portfolio, then focuses on his students, and uploads their work. Pretty soon, Spyros has (maybe)taught the next Ansil Adams, Matthew Berry or whatever.

        Will the business run itself? Certainly not. However, Spyros can certainly contact the local community college or university’s counseling office (which usually have job placement programs) and ask for an Accounting 202 kid for a couple of hours a week. Etc., etc.

        But how do you advise people that have no idea who you are, while maintaining good feelings?

      • Well said. The “overwhelm” is exactly what gets me.

        The amusing thing is I already go slow, I’m a plodder, which I used to fell bad about, like I was falling behind everyone, but I finally realized and accepted my pace, which was a big step for me.

        I’m the tortoise, not the hare. 😀

        Here’s to V 0.1.

  14. It’s really crazy how much can be done with $100, a little brain power, and some good old fashioned hard work. I always love reading your content Tyler, and I decided right away to sign-up to your newsletter…looking forward to getting updates about this project.

  15. Like Eileen posted above, ‘Lack of heartfelt confidence.’ Intellectually, I know I can start this business (providing background search services), but lack of confidence makes each step I take tentative. I AM taking steps though, and it is my hope that joining venues like this will encourage me.

  16. Sometimes having a community support group for this kind of thing can make all the difference. I think that a lack of confidence often comes from a lack of specific knowledge about something rather than an overall lack of confidence.

    Like you said yourself, you know you could do it…if you knew what to do. That’s the problem I’m aiming to solve with this project:

    You bring the ambition, we’ll provide the guidance so that you head the right direction and the accountability so that things actually get done.

  17. Tyler,
    Love this. You already know that I love bootstrapping because I did it myself – – and escaping the toxic workplace (what I help people with) was not easy but it was necessary because I was slowly killing myself doing work 9-5 and that I also disliked….I can attest that $100 can sure go far, it took me less than that and about 24-hours to create a side business which allowed me to escape…but….that was just for income – – and I had to make many adjustments to my “lifestyle”. It’s all worth it. Now I can finally say I’m doing the work I was meant to be doing….

    In my mind, there is only one thing that truly matters…..your will and tenacity.

  18. I seemingly have a pathological aversion to concentrating on a project and seeing it through to the end. It’s like I intentionally distract myself from the opportunities right in front of me.

    • Why do you think that is, Eugene? A lot of other commentors have mentioned a fear of success and what their project will turn into if they keep at it.

      What goes on in your head when you decide to abandon a project? I’m curious.

  19. That sounds amazing!! I would love to join. I’m only recently finding the value in community of likeminded people to help you along the entrpreneurial journey. Whether it’s business or emotional support or both it’s so worth it!! Sometimes it still amazes me how people make a living out of blogs. I mean, I know you sell a couple ebooks but you don’t strike me as the type who is super markety/sales-y (which is awesome) unlike others I’ve come across. So I wonder how the non sales-y people sustain themselves? How do a couple ebooks (such as you have) and a blog REALLY sustain someone?? It still boggles my mind! But in a good way. :)

    While I did go the quit your job route that you advocate, I do think moonlighting is quite smart and I am even a bit jealous that I don’t have the opportunity to do this! It would definitely make the transition a bit smoother but I love to bootstrap! And if I can make just $300/mo, it IS enough in the Philippines where I’ve set my base! Yup, it took me less than $100 to start a business too. All you need is a laptop and internet connection. I mean, seriously. 😛

    Keep it up Tyler!

    • I remember not that long ago when you were just starting out, Janet. I’m so glad to hear that things are working out for you. I love success stories like these, especially when they include cool tactics like moving out of the country to live cheaply.

      And perhaps a good lesson module for The Bootstrapper Guild would be “How to make a living when you’re the non sales-y type.” :)

      The truth is, while Riskology.co does support me full time, I do have other projects going on that supplement my income.

  20. A coffee shop. #1 thing stopping me is the cost and also because I’m under 18. Not to mention I’m going to college full time, etc.

    • Do you want to run a coffee shop, or do you want to run something that gives you the same feelings and satisfaction that a coffee shop would give you? There’s no wrong answer. I’m not leading you anywhere with that question.

      If you really want a coffee shop, there are ways to do it; even in your situation.

      However, starting a full on retail-location coffee shop is definitely a tall order, and there are lots of ways to get started much smaller and perfect your business model before going that route.

      This is going to be a major pillar of discussion inside TBG.

  21. Great idea! I messed around with Google Ad campaigns until I came across the profitable idea of running beginner’s photography courses out of my dorm room at University. I think the $100 businesses are key to growing entrepreneurs. Looking forward to it!

  22. I definitely fall into the category of people that dream big and then fall into a state of inertia! I have an idea for 2 books I want to write, and a tutoring business I want to set up.
    Its the doing the research part that is stopping me with the books at the moment, but having just arrived in a new country, I am beginning to create my routines bearing in mind that I want time to read and write. So in the next few weeks, I will be starting on those!
    With the tutoring, its a combination of a fear of not being good enough (I want to teach English as a foreign language) and not being sure how to reach out to my target audience. I also want to help children that are falling behind in school, but I’m not sure how to fit that in with everything else.

    All of this and more is the explicit focus of the next 12 months though (there’s a Plan, as well as a 1% List on my blog), so I’m sure I’ll work it out. Would definitely appreciate the support of fellow entrepreneurs though!

    • Hi Annika,

      Sounds like you have a lot of different options that you’re working on. That’s good–the “spaghetti against the wall” method can quickly show you which option is going to work best. Or, if you like all of them and don’t mind moving more slowly, you can keep doing both. :)

      If you really want to teach ESL, there are lots of opportunities all over the world to teach on short contracts without really any native language experience. In that case, your clients are the schools themselves, but there are programs that place people in the schools as well.

      Of course, going that route isn’t really the same as starting a business, but if that’s what you really want to do, it’s one option.

  23. What’s the #1 thing keeping you from starting the business that’s been kicking around in your head?

    Finding the intersection of my skills/talents and what people would be willing to pay for. I have many skills (computer programming, project management, writing, workflow optimization, and so forth), but don’t feel I have achieved mastery with any of them — a jack of all trades, master of none.

    My current corporate job seems to further this…I feel the skills I’m gaining really mostly only pertain to the cubicle nation — I’m learning a lot about little, and a little about a lot.

    • Those are all really monetizeable skills, Jason. Especially the first two. I think it’s worth remembering also that you don’t have to be the world’s leading expert on something to create a business from it. You only need to be better than the people you want to help.

      And, if you’re getting paid for it, it’s easier to keep doing it and get better and better so that you can keep moving up the food chain, so to speak. Don’t wait for perfection!

  24. Putting aside the many excuses I’ve given myself, my biggest obstacle(s) are my endless neuroses. At twenty-two, living in my mother’s apt, working part-time at a Wal-Mart (yuck), and not having ever completed any reasonable amount of college or developed any skills in my time on Earth, I can’t imagine a starting point for myself–In anything. I’m too anxious. The clock is always loudly ticking and my mind always fumbles to find a quick way out of it all, but it amounts to little more than vague fantasies.

    • Interesting, Matthew. I think being an entrepreneur actually requires a little bit of anxiousness, though. Of course, it has to be balanced with an understanding that building a viable business takes time.

      If you can focus on one of those vague fantasies long enough to pick out a “next step” action, you can take that a long ways.

  25. I am currently putting pieces in place to restart a small business. I stopped operating the business a few years ago to finish grad school, and I want to resurrect it. I have two fears: 1) will I find new customers (self-marketing); 2) I REALLY want to quit my day job but I don’t know where to find decent health/medical coverage that I’ll be able to afford in the beginning.

    • Yes, healthcare can be a real concern for some people. I actually don’t currently have it, so maybe I should get an expert to share some advice. That might make a good module for TBG.

      As for finding customers, I think you might be worrying too soon. If you’ve done it before, you can probably do it again. :)

  26. Tyler,
    Your blog is great! Like so many others here, it’s the fear of failure, the procrastination, the starting big syndrome & maybe even the fear of success that have hindered my even starting. But, I’m not sure how I can make my website for teenagers into a profitable one. I’d love to showcase teen entrepreneurs’ products (clothing, music, inventions, etc.) on my site, but not sure how to start. Any ideas?

    • Hey Monique,

      See above for all the others with the same fear of failure/starting too big problem. You’re certainly not alone!

      As for the business idea of showcasing teen inventions, I think the most important thing to think about is who the actual customer is, because it’s probably not teens. Who has the money? Who is going to actually buy the things that you showcase? That’s who you really need to focus on. Finding the people to showcase their inventions will be the easy part.

      Maybe the best way forward is to focus on a specific niche of teen inventions that you can nail down and then expand into more later on?

  27. Honestly, I’ve never really thought of starting my own business. I think I’ve been intimidated by the idea, partly because I thought I had to start out too big like you said most people do. Now that I see that a start-up doesn’t *have* to take off right away or cost a lot to begin, I think I will definitely give this some more thought! Thanks for the motivation. :)


  28. Hey Tyler, loving the sound of this. Question: I launched a little business project a few months ago. Is The Bootstrapper Guild more for folks who haven’t already started, or would it still be something I might benefit from?


    • Good question, Niall. The Bootstrapper Guild will cater to those who *recently* started and are trying to figure out how to scale up as well as those who haven’t started at all yet, but are committed to getting started *now.*

      The lessons that we’ll focus on every month will be evergreen–useful no matter what stage of progress you’re at–but the way we implement them will be tailored depending on where you’re at.

      Does that make sense?

      Also, there will be a 24/7 community forum where you can connect with everyone at the same level as you as well as learn from those ahead of you and help those behind.

  29. Hey Tyler-excited for this project. The “one thing” that’s been holding me back (seems to be a common one) is focus/i.e. full commitment to an idea. I’m slowly allowing certain activities go to bring more attention to things I enjoy doing & am slowly improving at. Any input on how to make commitments (& enjoy the process :)) is greatly appreciated. Cheers -George-

  30. I’d have to say that the #1 thing keeping me from starting another business (because I already have a small-potatoes fine-art photography business), is the time I feel like I have to devote to my well-paying, stable, soul-killing office job with great benefits.

    I know, a stable, well-paying job? In this economy? Poor me!

    But I do want to find some way to reconcile all my interests to find harmony between doing what I love and earning a decent income. Right now I’m stretched between my photography (creative), desk (income and writing), teaching at the gym (active), and family (personal) activities.

  31. I’m at a crossroads in that I’m acutely aware that my current full time gig will eventually come to an end and I would like to set myself up with something that I can call my own, not reporting into some ‘boss’ who would basically drop me if the need arose. Its the fact that employees are ultimately disposable that drives to want my own thing. The illusion of ‘security’is what keeps most people stuck in cubicle-ville but I’m wanting to plan an alternative course of action now for my own sanity.

    I’m aware of my own skill set – writing copy, public speaking (I’ve been paid for both these activities before (ad hoc), but taking them full time is the challenge to overcome) and I also feel I have the ability to coach/teach to a high level. I’m struggling to mesh my skills into some kind of income producing activity (I had an initial financial target of creating enough to cover my childcare costs…yes, I’m a parent) I’m sure once I ‘break the seal’and create a focussed plan it will be ‘game on’so to speak. My other desire is to find a way to work with a specific group of athletes on developing their ‘mental game’which will require a) some formal training (costing $$) and b) a way to market that knowledge in a saleable format. So, that’s where I’m at… not too complicated at all really….haaaa!

  32. What I am struggling with is when to go from version 0.1 to 0.2. I started my little side business 2.5 years ago doing custom longarm quilting. I got a good deal on an old machine which has gotten me off to a good start. But i am to the point where my dinosaur of a machine is holding me back creatively. I would love to be able to do this full-time someday and leave my current job, but to do that I would have to increase my workload 10-fold. my husband thinks I need to focus on self-promotion and getting a larger customer base, but I feel I can’t do that unless I have a better machine. It’s a chicken and egg thing. a new machine will cost at least $10,000- which scares me. I am very hesitant since my full-time job pays the bills. Oh, and we are expecting our first child in January.

  33. I have a sign on the inside of my door that says, “Opportunity NEVER knocks! It LIVES here!” Or I will as soon as I actually get around to making that sign.

    ADD. I have a dozen ideas and can’t commit to any one for more than two or three days. Perhaps related to Eugene’s issue, I pursue an idea until I get to a part I don’t know how to do. Then I start something new. My life is a collection of half-finished projects. This leads to that fun fear/procrastination/self-loathing cycle that confirms that I will never be successful at anything.

    I’m a great P.A. but a lousy Boss. I amass tons of ideas, options, resources, but can’t choose one. Ask me “What is there?” and you’ll be amazed at the breadth of my knowledge, the depth of my insight, the height of my creativity. Ask me what I want and you’ll think I’m an idiot. I’ll take a step in one direction, change my mind and go another way; I feel like I have one foot nailed to the floor and I’m spinning in circles.

  34. Clarsa,
    You dont know how much you’re NOT ALONE. Youve described me to a “t”. My personality is an idealist, like you. We need to find others whose strength is execution. Im joining Tyler’s Bootstrapping Guild to MAKE myself focus on one idea I believe can be turned into a successful business. Challenge yourself to do the same; thats part of the reason its being created. Good luck my fellow idealist!

  35. Thanks for the welcome, Monique. I look forward to working with you.
    My research uncovered the idea that there are two decision-making styles: maximizers and satisficers.

    Maximizers (including me) correspond with the research, “idealist”, or great-idea portion of a project. We scrutinize the problem to uncover novel insights. We brainstorm and turn ideas over in our heads to find exactly the right solution. Then we figure out the most economical way to procure what we need and the most ergonomic way to use it. Even after the thing is done, our minds are engaged in thinking how we could have done it better, gotten the widget for less, etc. We suffer “buyer’s remorse” constantly for everything we did, and everything we didn’t do. Sounds exhausting, doesn’t it?

    A huge maximizer problem is that the first step is always deciding what problem to focus on. Even after we’ve “decided”, we’re still evaluating all the other problems we’d identified, and all the new things that come up. Would this make a better business? Could I get into that business faster or with a smaller investment? Do I need to choose one or can I do both at the same time? Should I be starting a business at all when I can’t even get the spare-room cleared of my accumulated half-finished projects?

    Satisficers (a pormanteau of “satisfy” and “suffice”) have a basic criteria and grab the first solution that comes to hand that meets that. Those are your “execution” people. We don’t get along with them because they are bossy and judgmental and fail to appreciate nuance. :) They get things done. They don’t bargain-shop; it ain’t pretty; and it may not last. But it’s done. Down the road, when some snap decision the Satisficer made turns out to have unconsidered consequences, the Maximizers are ready with a dozen solutions (and probably an “I told you so.”) A good Satisficer takes it in stride because he is already doing thing #23 down that list and has let thing #1 go.

    Most importantly, to me, Satisficers tend to be *happier* people. Second-most-important: they are more effective.

    Sounds like the perfect solution is for the two to work together. But their ways of perceiving the world and communicating are so alien to one another, this is difficult. It’s easy for this to become a Master/slave relationship (resentment for everyone!) and hard to keep it a partnership of complementary equals.

    There’s a middle road: Optimizing. This is a compromise between the very absolute perfect best solution and some slapdash band-aid job that’s going to fall apart in the near future. Unfortunately, a Maximizer sees this as a reason to think even harder and evaluate even more, because maybe her solution is *maximal* but not *optimal*. A Satisficer has an easier time becoming an Optimizer; just add a criterion or two, like how long the fix needs to last, or whether it needs to be less expensive.

    Had you encountered this conceptual matrix, Tyler? Will you be making use of it in Riskology?

    • I am 110% a maximizer. It’s caused problems in the past, but I have a few tricks that I use to deal with it. Could make a great topic for Riskology.co and for The Bootstrapper Guild. Thanks for bringing it up.

  36. The number one thing keeping me from starting the business that I’ve been kicking around in my head is that I know it won’t scale, i.e. it’s something I could do with some spare time, but should it ever become even modestly successful there’s no way I could fulfill all orders simply because of the nature of the product (which is rather bespoke or customized, not to an extent requiring large amounts of labor, but enough to potentially be overly time-consuming). This could be solved with a large amount of expensive equipment, but at some point even that might not be sufficient and I’d have to design an entire infrastructure around an idea that’s honestly not all that cool.

    I suppose I wouldn’t know until I tried it though, so perhaps I’m overthinking this and should just take the first step.

  37. […] The Simple Secrets of a $100 dollar business. – While you might not always be able to cover every start-up expense with $100, lack of funds should never stop you from trying things out and starting new projects. Tyler Tervooren explains the concept behind the $100 Business Idea, and frankly, it’s exciting. There’s something to be said for starting out small – there’s no shame in beginning within your means and making some money before adding every single feature you can imagine. […]

  38. The one thing I think I deal with the most is poor time management. I work 2nd shift, which splits my day right in half, limiting my time on both ends. On top of that, my wife works 9-5, limiting our time, and we have a new baby, limiting our time further. To complicate matters, I’m prone to procrastination…

  39. Our-my son and I- main obstacle is pure, all-American laziness. We have the time, opportunity, and the know-how but we are lazy about getting started. Lazy, I believe, because we are in a good financial position right now with no real need for cash. Now, however, after reading this article, I want to get going. My butt has been kicked by finding out that I, a grown man, am being outperformed by youngsters in the business starting arena. My son and I are going to build outdoor wood furniture, namely the adirondack-style chair. Haven’t spent a penny yet and we have everything except for a source of cheap wood. Now if I could just get off my lazy butt…..

  40. Hey, right now I’m doing freelance webdesign/graphic design work but I really want to use those skills to start a local Tshirt company in my area… I’ve made a shirt in honor for a deceased friend and people loved it wanting to buy it even though they didn’t know my friend. Only thing is my other buddy funded the project all I had to do was design it. Now I want to get this Tshirt company flowin’ but I have no experience with printing or what-not and well… Haven’t gotten around to it. Plus it’s hard finding freelance work for my webdesign services, most of my work is just me bartering webdesign for someone else’s services- Chiropractic, yoga sessions, etc. I need that $$$ to flow in. The mantra I chant, “Money flows through me, I am prosperous.” Isn’t working very well lol. I guess some encouragement or advice will go along way. I am reaching out after-all… Thanks.

  41. The main thing keeping me from starting my business idea(s) is probably the fear of failure; I say it’s other things, I put the blame on say, lack of initial funds, the difficulty of finding customers, inexperience running businesses, lack of knowledge about the legal side of operating a business, etc. but these are all excuses; I am good at research and I know this, so I could figure out all the ins and outs legally; I can connect with people to try to find the customers to get it off the ground. Everything else seems like an excuse for the fear, which I’m just realizing now.

  42. The #1 thing keeping me from building a start-up is my fear of having no demand for the products I sell. My side start-up dream is to make industrial (concrete, metal, wood, etc.) home accents (planters, lamps, vases, and decorations) and progress to making furniture. I live in a small city in a small state and I’m not sure that the style will be in demand. I do want to start an Etsy shop first to make sure.

  43. I am a medical student by day and most of the week with a huge drive towards entrepreneurship so i didn’t let the busy schedule stop me when I registered my home based internet business sourcing in small quantities at a time. I even managed to start a domain developing business (buy – build – flip ) earlier this year from which I learn a lot on a daily, however have not yet made much from it, except from the Adsense I don’t have potential advertisers filling up my inbox. I want to create a holding company for less than $100, adding two more businesses to the stable by the end of next year. Victory is certain.

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