
New registrations to my latest business project, The Bootstrapper Guild, closed last Thursday, and I’m happy to report we have over 100 new members just getting started on their journey to micro-business ownership.
I want to share some quick stories from the launch to illustrate a few lessons I’ve learned about launching a business project, how to treat customers, and the importance of your attitude when it comes to success.
Hugo Makes the Most of His $1 Trial
One of our new members, Hugo, came into The Guild the other day and immediately put up a progress report with all kinds of goals and big numbers that he wanted to see happen in his new business right away.
This happens once in a while and, normally, I jump in and say, “Whoa, let’s back up a few steps here. Do you have any idea how you’re going to do these things? Let’s work on that.”
But in Hugo’s case, he didn’t just have big goals, he had a plan to meet them, too. So, I told him I was going to sit back and watch for now, and that he could ask any questions he liked.
Two days later, Hugo reported his very first sale—$100 for doing some custom web design work.
I think pretty highly of The Bootstrapper Guild, but this success so early is clearly more of a result of Hugo’s attitude and determination than two days worth of instruction.
Lesson: Education can tell you what to do, but only your own motivation can make you actually do it. The Bootstrapper Guild helps do-it-yourself entrepreneurs figure out the right steps to take, but our most successful members are the ones who actually take them. Never substitute learning for doing.
How I Accidentally Hired My First Employee
On day 2 of the launch, a new member, Mike, signed up, and revealed he already had a successful business going, but wanted to see what he could learn from TBG.
When the first few lessons were clearly beneath him, rather than ignoring them or dropping out, he started helping other members with their questions.
What was I to do? Mike was clearly too advanced for the lessons—at least in the beginning. I saw two options: Wait for Mike to see that he’s beyond the instruction he’s getting and drop out, or offer him his $1 back and send him off with some pointers he could actually use.
Then, I thought of a third option: What if I hired him?
A few emails later and we had a deal. The Bootstrapper Guild just got a lot better.
Lesson: If you run a business and have a customer that’s talented with a desire to help people, don’t try to figure out how to keep them as a customer—hire them!
Celebrate Your Mistakes (And Apologize for Them, Too)
On the opening day of the launch, my developer and I were scrambling to get a few last-minute bugs worked out of the system before opening the doors.
We thought we’d fixed everything, but guess what: We didn’t get it perfect!
That first day, some people came to the site but weren’t able to order because of a technical problem that we’d missed.
Oops!
We fixed the issue, and my first thought was to just sweep it under the rug and move on with the launch. That’s usually the best solution; you can’t change the past so you might as well embrace right now and get on with your day.
Then, I thought, “What if I’d been a customer that wanted to buy something but couldn’t through no fault of my own?” I’d probably be a little annoyed. So, I decided to send a humble email to everyone apologizing for the mistake.
The result of that email? An immediate 25 sales.
Lesson: Sometimes, being the nice guy and doing the right thing pays off.
A Very Good Reason to not be a Used Car Salesman
I’ve learned a lot over the years about how to sell things. If you want to run a business, this is not optional education!
Last week, I bought a car. I thought it was a good one, but I honestly don’t know much about them. Turns out it was a lemon. I returned it (less $150 for the salesman’s “trouble”).
The guy who sold me this car was a classic used car salesman. “Look at these cup holders. Nice rear view mirror, right? Isn’t this car a pretty color?”
“How many miles does it have on it?”
“Don’t worry about the miles! Worry about how hot this cigarette lighter gets! Look, the horn works!”
Through the whole process, this guy gave me the hard sale. “You need this car today. I’ve got a buddy who’ll give me $100 more than you’re offering. Are you ready to buy?”
When I launched TBG on Monday, I was determined to use Mike (the sleazy salesman) as an example of how not to sell something.
Most books you read about sales will tell you that Mike did everything right. And in a way, it’s true. He did sell me the car, after all. But then I returned it, and I’m not planning to buy one from him ever again.
Where most books about sales fail is in forgetting to mention that a good relationship is far more valuable than a one-off sale.
If you sell cheap things and never plan to see or work with your customers again, then go ahead and follow the old “ABC” sales advice: Always Be Closing. But if you sell something even remotely expensive or have any kind of interest in building long-term relationships, put that first.
Just before we closed down registration this morning, I sent out one last email. It was brief and basically said, “The doors are closing. If you want in, get in now. If you don’t, no problem!”
No hard sale, no pushing, no guilt trip or distractions. There will be more opportunities, and when they come, people will think about signing up then, not about how annoyed they were the last time around.
Lesson: A customer that stays with you for the long-term is far more valuable than 10 that come and go. Try to sell in a way that builds relationships and not animosity.
Treat people well, look for opportunities, and take action when something good is right in front of your face.
Best of luck with whatever you’re working on now. If you missed this round of registration for The Bootrstrapper Guild, you can get on the waiting list over here, and I’ll let you know when we open again.
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Image by: DavidDMuir

I’m new to your site and was VERY tempted to join the Bootstrapper’s Guild — just couldn’t come up with a something-to-do. It should probably be noted that I’m closing in on 70 and am rather amused that I find myself checking out the sites of 20+ year-olds for life insights. I’ve done lots in my time and have taken a few life-changing risks to boot. Often, though, (and this is where you come in) I get an idea and think — would I like to do this again, and again? Well, no. It’s the locked-in part that scares the hell out of me. I’m the one who once got married against my own will — now, THAT’s risky business. Won’t do that again. I think.
I’m not sure there’s a real question here — it’s the courage to put myself out there and stand up for myself -yet again- that challenges. That, and knowing (here, you come in again) if what I think I want is what I really want. I have lots of skills and lots of interests — makes it very hard to focus. Most things have come easily — so, I have a low frustration threshold for steep learning curves, and always something else to pull me away.
Still, it would be fun to find a way to make a few dollars by pulling up my bootstraps and using my own wits. Finding a job working for someone else is much, much easier – and I can make any job interesting and fun (for a while anyway) – I suspect, though, I’ll get much more satisfaction figuring it all out for myself.
One of these days, I’m going to screw up my courage and put myself on your waiting list — I think. Commitment is hard.
Ethel,
There’s no rule that says that you have to stick with whatever you pick forever. So what if you want to change every week? It’s your life. Do what makes you happy.
If you want to grow something into a huge success and impact tons of people, then it will generally take time, patience and commitment. If you want to do things purely for the enjoyment, then do them and change at will.
With your many skills and interests, the only way to know if any of them are right for you is to do them. Experience is invaluable. Reading and thinking about things only go so far.
You have to get out there and do it to know if it’s for you.
Oops. I forgot to click on the “Notify me” box.
Tyler,
i joined last week for $1. Finding it to be very helpful. sorry if this sounds a little stilted. i’m always so self-conscious when writing for mass consumption (you know, those millions who are just waiting to read my words.) but that, i guess, is one of the biggest parts of what i find so great about the guild.
i’ve got a micro- — make that ‘eensy weensy’ writing biz already. so i don’t feel a lot of pressure to stick to the timetable. and that’s working for me.
what i’m finding so helpful is 1) reading others’ stories and seeing the proof that there are others out there just like me working to get their ideas off the ground; 2) getting practical tips; 3) taking a ‘bottoms up’ approach to biz building; & 4) being part of the group, knowing that — well, something about knowing that i’ve put myself out there and said i am gong to do this — even if no one really is paying attention. i know i said it.
yet, what i’ve realized is that i do best working at my own pace. it’s an intriguing combination. since joining the guild, i’ve become much more motivated – and committed – to working on my project. but, given that it’s in such an early stage — i’m developing a learning system, sort of a ‘basic facts mastery’ approach to learning — and i have to develop a working model before i can really move forward (not exactly true and i am moving forward in other parts of the biz — exploring website development, reading others’ info on the nuts and bolts of an online presence, etc, etc.) But it’s at my own pace.
so i guess i am saying all this to say ‘thank you.’ what a great project you’ve got going here. and, please don’t mind if i modify it in a way that works for me. i figure as long as I KNOW that i am working on my project, it’s money well spent, irrespective of whether or not i meet a 60 day / $200 per mo. goal. right now, my goal is to get my working model working.
again, thanks Tyler.
buddha bless
Really glad you’re finding it useful, Mark. And it’s really up to you how you go about using the site. If you have a system that works for you then, by all means, keep at it.
Cool to hear the “behind-the-scenes” lessons!
Just curious, is there a reason that you only open the Guild for a limited time, rather than making it a “join anytime” type of membership program?
I’m interested in your answer because I’ve got a membership site in the works myself, and am trying to weigh the advantages of different strategies.
It’s better for the community. That’s the main reason why. When a group of people all come in at once, they kind of bond and make connections that are less likely to happen than if people slowly drip in over time.
So, that’s why I chose to do it like that.
Also its a good business strategy, people will want things more if they are less available.
Now I’m kicking myself for not joining!