Starting a bootstrappers group

In the drinks after the first Life Time Value conference last year, two different friends hinted that it would be great if there was a local meet up for people who were trying to start their own ‘product’ businesses. They were telling me partly because they were interested to see if I would come along, but mainly because I’ve organised various groups and events before, and they wanted me to do this one. After some humming and haaing, and checking another friend would come along, I said yes.

I’d been in a group of people trying to bootstrap their own startups before. In 2009 Jon Markwell (now co-organiser of the Life Time Value conference with Andy Croll) organised a weekly meet up for people trying to get their own product or service up and running. Even though I later burnt out on the idea I was pursuing then, I’d found the group very helpful. Even better, Jon said he’d both come to this new group and lend us part of his coworking space, The Skiff, to hold the meetings.

After some asking around within The Farm and Skiff communities, we got eight people together for our first meeting in August 2016. A mix of developers trying to work on Software as a Service (SaaS) or WordPress plugin products, and a marketer looking to build on previous success with an ebook by building more, all with existing businesses as freelancers. Some already had some income from products, most of us were starting from scratch. Over the months we’ve added a few more people in the mix, all along the same lines.

I was reticent about starting another group at first. I’ve got a lot of freelance work on and knew I wouldn’t be working on my product for a few months. I didn’t want another distraction from my work and running the Farm group. However, looking back now I’m glad I did.

What we’re running is not a ‘mastermind’ group in the normal sense, as there are too many of us. It’s a meet up of like minded and like motivated people, to talk about what progress we’re making with our businesses.

We’ve now had ten meetings over ten months. This is what I’ve learnt so far…

Why be in a bootstrappers group?

  • Motivation
  • Exchange of ideas
  • Sanity checks
  • Sharing the boat


Building a product of any kind, large or small, is hassle. It’s a change from your normal life, whether you’re a freelancer or employee. Once the fun part is out of the way, it becomes a grind. To some people the fun part is having the idea and sketching out a flow of how an application will work, for others it’s getting all the information together to write an ebook, for other’s it’s coding up a basic version which may look horrible but gives the functionality they want. Once you’re past that, keeping going to make the product useful for other people is a stumbling block you usually don’t face.

In my normal work, I make websites for people. I don’t have to think about whether the site is right for the business, or whether it really fulfils a need, that is the concern of the person hiring me to build the site. I don’t have to worry about whether the copy is convincing, the imagery, or anything apart from making the site work easily and quickly. Keeping going is simple as they’re relatively small projects and I’m getting paid regularly for doing them.

Compare this to making a product – you don’t know if anyone really, really wants it, so you should carry out customer validation, but that’s another set of skills and methods to learn. You need to talk to a designer or come up with a design yourself. You need to design the flow of how the thing you are creating will work or read. All of this is speculative until you can get something out in the world and then find people who really do want it and will pay for it.

Fortunately, there’s loads of advice around on how to do all of these things, and building a product based business is the easiest it’s ever been online. However, doing it all is hard because it’s different from what you’re used to doing.

Giving up, or putting off working on your product is easy, especially if you’ve got client work to do.

I’ve found having a group of people I meet every month to go over what we’ve done and what we’re doing to actually get on with our products is a great way of staying engaged with actually having to get stuff done on the product I’m trying to make. Knowing meetings are coming makes me want to get stuff done so I’m not sitting there in front of people, again, saying I’ve got nothing done.

Exchange of ideas

In the village I live in, there aren’t a lot of digital product businesses. I know of a whole one. That makes it hard to bounce ideas off people, and get inspiration from their ideas. Having a meeting to do that in face to face in a nearby city is much better for creativity than just doing it over mailing lists and forums. As well a receiving help, being able to help someone take their idea in a new, and potentially more profitable, direction is a great feeling.

Sanity checks

Got an idea? It’s probably crap. Even if you’re in the stage where you’re enthusiastic about your idea and want to drop what you’re already working on to work on this new, great idea, it’s still probably crap and you should finish what you’ve started. Having people to say that to you you know and respect is very helpful.

Sharing the boat

Just knowing other people are struggling with building their idea, or struggling with marketing their idea, or with some of their customers, or with… Every facet of a business is hassle to someone. Being able to meet and know other people are going through the same pains as you is a great help. We’re all in the same boat.

Also, “a rising tide lifts all boats”. When one of us finds a tactic or strategy that works, we can tell the others and all benefit.

How have things gone?

For me, middling, but that’s partly not having much time to work on my product, a situation I’m trying to solve at the moment.

For others in the group – some people have dropped out either because of moving or not finding the group helpful. Others are finding it very helpful, apparently. However, looking at it objectively, I’m not sure a lot of progress is actually being made. I need to keep an eye on whether the group is just a talking shop or whether it’s helping people make actual progress.

What we’ve done right

Having a core group of people who are coming along regularly is helping us understand each other’s businesses and push each other on usefully.

Having a ‘check in’ session (suggested by Jon from the ‘stand ups’ used in agile project management) each meeting where we list what we’ve done recently, what we’re going to do next and any blocks to what we’re doing definitely keeps a focus on actions.

What I’ve done wrong / what we haven’t worked out yet

We started having a regular day to hold the meeting, then started to move it to make life easier for some people. That hasn’t really worked out as half the time, those people still don’t turn up. Switching back to a regular day would be sensible at this point.

Communication – I set up a forum as I think it’s a good way to store information within our community long-term, but it is a little clunky. I didn’t want to go to Slack as I find useful information in Slack is hard to find and disappears quickly in to their archive unless you pay an amount I wasn’t willing to spend. I’m not sure if it will resolve itself as time goes on, I plan to post more of my findings in to the forum to help it be useful and see where things go with it from there.

Turning in to a talking shop – too much talking about ideas and not enough progress. This happens especially if someone new and someone who hasn’t come very often are in the same meeting. We re-tread old ground to no one’s benefit. Resolving this is to probably not add new people to the group, and encourage people to attend regularly. Part of me thinks I should kick people out who show no progress, but I don’t think I want to deal with the stress of that at the moment.

Record keeping – I was making notes from each meeting and posting them in the forum but this was very time consuming. I went to recording the meetings and sharing the audio file for people who did not turn up, but I’m not sure that’s as helpful as the notes and still takes time. I need to think about recording or getting people to post at least a short entry on what they have done recently and what they plan to do next.

Benefits are all existential – I’ve realised recently the group has been going long enough that it will probably keep going, and we should have some public information about the people in the group on the website and some promotion of ourselves as a group. However, this takes time away from other things, so will probably not happen any time soon.

Has it helped?

I think it has, but I’m not sure it is helping enough for the time I’m spending on it at the moment. I am making progress, and it probably is in part because of the face to face meetings. However, it’s also being hassle to run and I’m not sure that hassle is currently being offset by the help it’s being. I’m in a few online communities which are helpful too and although I think the face to face meetings are being more helpful, it’s tough to be sure.

This leaves me in an awkward situation currently – putting more time in to the group to make it more useful to me, or stop running it to save time?

I will mention the problems I think the group has within the group and see what people think resolutions could be. As with the whole point of the group, that could inspire some new ideas that will get over the problems.

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