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What Pokemon and My 10 Year Old Son Taught Me About Bootstrapping

My 10-year-old son loves Pokemon trading cards, though for the life of me, I don’t understand why. Lately, he’s been taking initiative around the house, doing odd jobs to earn money.  Now that he’s got some cash, he’s eager to burn it on a $12 pack of 60 Pokemon cards, and is badgering my wife and I to take him to Target so he can buy them.

Being a cheap bastard, I think $12 for 60 cards is an outrageous ripoff, and I told him as much (leaving it to him to figure out that I’m a cheap bastard).  My wife and I refused to let him spend $12 on 60 cards, and I suggested he find some other way to acquire Pokemon cards.

His first ideas were even worse:  He said he could buy 25 cards for $8.  Or that he could trade them with other kids at school (keep in mind that the school prohibits buying/selling/trading stuff…), though the last time he did that, he got ripped off by one of his friends (which is exactly why the school prohibits this kind of thing).

I told him about start-up companies that start with little or no funding, but have a lot of needs:  computers, office space, furniture, employees, marketing, etc., and how they have to bootstrap to make things work until they have enough cash to pay for the things they need.  I told him that bootstrapping often means figuring out workarounds to get what you need in a cheaper or alternative way.

He thought about that for a minute, then asked me to think of some ideas for him. Brilliant. He was already trying to outsource.

The point is, we often can’t get what we want when we want it.  Typically, it comes down to not having the time or money.

Constraints are hidden opportunities

But bootstrapping is a fun and interesting thing.  The constraints often force us to be more creative and come up with better solutions than we would have otherwise.

Bootstrapping is a different mindset, and it requires more flexible thinking, but the benefits are well worth it.  Here are a few examples:

#1:  Phone & fax service

I was talking with a small business owner down the hall in my office building, and she was thinking of having the phone company install a landline for her phone and fax.  I didn’t know how much it’d cost, but I knew it’d be expensive.  Instead, I suggested using Skype and/or RingCentral for calls & faxes; with Skype, I get unlimited calling and my own phone number for about $60 a year. That’s a lot cheaper than a landline, and I’m not limited to making calls while in my office–I can make calls from anywhere.

#2:  Signing documents

Clients sometimes send me a nondisclosure agreement (NDA) to sign.  I used to have to print out the NDA, sign it, scan it onto my old, on-its-last-legs PC, then get it onto my laptop so I could send it.  I hated the whole process.

Lately though, I’ve been using an electronic signature service (E-sign) to get & give signatures.  It’s cheap, and super quick & easy.  I also use it to get client signatures on project proposals.

#3:  Scanning documents

I’ve also eliminated the need for a scanner by using an app on my phone to scan documents, convert them to pdf’s, and e-mail them to myself or store them in the cloud–all for free.  I love free.

#4:  Expensive business equipment

A friend of mine is thinking of starting a consulting business, and for his niche–telephony–he initially thought he’d need to spend thousands of dollars on technical equipment before he could start his business.  I mentioned that he’d lower his costs and risk by figuring out the bare minimum he’d need to snag his first client.

After some discussion, we came up with some ideas for things he could deliver without even needing the fancy technical gear; once he has paying clients–or signed project contracts–he could rent the equipment for a month at a fraction of the cost of buying the equipment.

In the long run, the equipment rental might end up being more expensive, but if he finds that his business fails, he won’t have sunk a lot of cash into equipment that he’d have a hard time unloading.

#5:  Website costs

Like expensive technical equipment, most business owners think that a website costs thousands of dollars.  Not true.  Even if you’re not a techie, you can get a professional website with a ton of functionality for less than $100.  That’s right–for a single Benjamin Franklin.  That leaves a lot of cabbage left over for other things–like medical insurance, your salary (yay!), or lattes–a lot of lattes.  For doubters, you can see exactly how in my free ebook.

The bottom line

So, rather than complaining about the constraint or problem, and rather than taking on risk by going into debt and/or overspending, figure out how you can get it done easier, cheaper, or faster.

There are tons of tools & tricks available, but the first step is knowing that there are other ways to skin the cat, and being flexible in thinking about what you need, and how to go about getting it done.  Sometimes it’s just a matter of rethinking what you think you need.

I can’t wait to see what ideas my son comes up with.  Maybe he’ll figure out some Tom Sawyer-like scheme where his friends are falling over themselves to give him their Pokemon cards.

Greg Miliates has been bootstrapping since 2007, and is obsessed with free & low-cost business tools.  He also has a blog for people starting & running their own consulting businesses:



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7 thoughts on “What Pokemon and My 10 Year Old Son Taught Me About Bootstrapping

  1. Norman G. says:

    Great tips, I enjoyed this!

  2. Kyle says:

    Which app are you using to scan documents? sounds neat.

    • Thanks for your comment!

      I’m using CamScanner on my Android phone to scan docs and send them as pdf’s.

      Another neat phone app that can save money–especially for point-of-sale transactions–is Square. POS systems can be pretty pricey, but Square is free, except for a small, per-transaction fee. I literally saw someone using it at their lemonade stand this summer. 🙂

  3. Glad you enjoyed the article!

    For scanning documents, I use an Android app called CamScanner.

    Another nifty app that can save money–especially if you do point-of-sale transactions–is Square (available for iPhone and Android). Typical POS systems can be pretty pricey, but Square is free, except for a small, per-transaction fee. I literally saw someone using Square at a lemonade stand this summer.

  4. Margaret says:

    Great tips – Auction houses are a great source of good quality furniture…

    • Thanks for the comment Beverly!

      Margaret – that’s a good tip, didn’t think about that for office furniture. Makes sense.

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