Apprentice bootstrapper

Hey guys I’m kind of intrigued by the idea of having an apprentice or something like that. Someone who is an aspiring bootstrapper.

Not that I’ve “made it” just yet but maybe I can help someone out a little bit who’s just starting.

I know that hiring an employee would probably be the most natural way to accomplish this. I’m not really planning on hiring ever though and don’t think that my people managing skills are very strong.

But I’d like to be able to help others still somehow. Maybe also get some help from them with support or something else - who knows.

Anyone tried this before?

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I think a lot of people would be interested if you tell them what how you can help them and on what (generic) topic: tech, business, sales, promotion etc


You know it’s funny - I’ve been kind of putting feelers out for this kind of thing for a month or two now and was surprised I didn’t get any takers sooner. I think that even when you’re literally looking to help people for free, you still have to market and sell yourself. Just goes to show how important marketing/sales are to basically everything.

So…I basically have had to do everything myself from building the product to marketing it, doing sales calls, figuring out pricing, the whole enchilada.

Not exactly sure what this relationship would look like (or what exactly I’d help with), but if someone is an aspiring bootstrapper looking for some help/feedback, they should get in touch and we’ll figure it out.


Hi Kalen,

I’m just getting started with my product (launched in mid Jan this year). Especially the marketing part of bootstrapping is really a tough nut for me to crack. I’m definitely interested in some kind of apprenticeship, but doesn’t really know what to do and where to go (except in my network, where I’m lucky to have a few people to reach out to eventually).

If you are considering doing more about this, I would love to get in touch about the subject.


Hi Kalen, first off congrats on what you’ve built with MageMail - especially with two little employees 24/7/365 that need so much of your energy! #superheroDads

I like where you’re going with this, as I’ve done this in the past and am doing this with a project I’m working on right now, a somewhat peer mentoring / skillset relationship.

How my brain would approach this would be to embrace the JTBD ( my biggest best AHA share to anyone this past year - Jobs to be Done) methodology - what Jobs need to be done in this relationship. So here goes, If I understand where you may be coming from.

Kalen loves sharing his knowledge, (maybe someone did it for him to help his company get up to speed and now he would love to give back) at the same time Kalen is pulling the solopreneur shift, and doing pretty much everything himself, boy oh boy would he love some help from someone who’s skillset is different from what he loves to do and is great at.

If only there was a mutual relationship where this could co-exist ( think IFTT - “If This Then That” )

At this point, not to be selfish, but you have to think what would work best for me, you don’t wont to start offering up 5-10 hrs of your week mentoring if there is on + energy coming back. There is nothing wrong with doing this if you can afford to, and the positive energy could just be gratitude, I’m all game if you can afford that. But it needs to be a win-win relationship I feel.

Start with what Jobs to be done you need help with. What areas are you lacking skills in, or just don’t like doing, or you feel your startup business needs to better excel at…from there try to match up with someone who’s skills are a fit and WHO (big important factor here) is ALSO building out a SaaS business and would hugely value the learning and experience you’ve gathered over the past 2 yrs of making mistakes and small tweaks or pivots you did that corrected your growth.

Another variable to consider is the expectation of time. Time-box what you think this could look / feel like for both of you. I do this now with mentoring someone with 2 sprints of 20 min twice a week over google hangout / skype.

These are just my $0.02 Canadian cents :wink:

I know I’ve joined this bootstrapped community to meet other like minded folks who are also building out there dreams and software / services to get what I call ‘freedom units’ ( aka money / financial freedom )

Thanks guys. I’ve been thinking about this more and also talked with a buddy of mine who took on an apprentice, and I think I’m leaning away from that idea specifically. It seems like it could get very complicated and there could be potential for one party to not be happy about it. I’d be opening up myself to all manner of lawsuits probably - who knows :confused:

I think probably the most straight forward thing is to just find ways to help other bootstrappers without getting help in return. That’s part of what I like to do on this forum and others but I just feel like I want to be a little bit more involved than just responding back and forth on a forum.

Not really sure what it would look like. I wish there was a site out there that faciliated these types of relationships. I did some searching before for mentorship type sites - there isn’t anything really great out there.

@petersuhm feel free to DM me and we can chat a bit more.

@Ryan_G thanks for the canadian cents (ya right the canadian dollar is down! Gonna need more like 3 cents!). I think you’re right that I’d need to better define what I wanted help with if I was going to go this route.

Hi @kalenjordan, I think it’s a great idea if you can find a match or two. Very good of you. might be the closest thing to mentoring.

Other thoughts. I wonder why someone wouldn’t take you up on it, like immediately? Might be partly that they’re holding cards too close to their chest, or unsure of your motivation, or aren’t considering what you could help them with, or don’t want to waste your time with their silly current issues?

If anyone has some other reservations, maybe post them.

Someone should really snap this opportunity up.

I wish I had apprenticed for a bootstrapped product owner a few years back. Looking back, you start to see how valuable first hand experience really is when it comes to doing your own thing.

Ya I think it just comes back to the fact that no matter what you’re trying to do, you have to market yourself, even if that happens to be giving away free advice and help :smile:

I thought of clarity but I’d rather not have the pressure of someone paying me money for my time - that feels a lot more like consulting to me than helping/mentoring. Also I’m not sure how much time I want to spend on the phone vs. email / etc. I’m really kind of gong through the process myself of figuring out what it would even look like to try to help more.

But again I think I’ve decided against the apprentice thing for now. Had a buddy who told me he did it and it didn’t go super well. If other people ahve done it before and it’s gone well I’d love to hear more about that.

@CasJam I kinda felt the same way. When I was starting out and trying to figure this out I would have attacked someone offering free advice :smile:

I sort of informally mentored a few people for programming, and no, it didn’t go well either.

I found two main problems:

  1. Some will expect you to do all the work. They don’t realise your job is just to guide them.

  2. Others will just go black, and you’ll be left wondering what happened to them.

I would just be more open, so people can email me anytime they want help with a particular issue rather than having formal apprenticeship.

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Thanks shantnu. Appreciate that.

Some will expect you to do all the work. They don’t realise your job is just to guide them.

This! It happens so often.

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There is also the issue that we tend not to value things we get for free.

I heard a story about a consultant who offered his time free to charities. They listened politley to what he advised and then ignored it. So he switched to charging top dollar, then they started implementing his suggestions.


Thanks guys - appreciate the feedback. @Andy ya I like the model that you use. You charge a reasonable fee but I’m sure that the fee is mostly just so that people will respect your time.


I’m kind of in a similar boat. I do have a few skills where I could probably help someone, but I’m not at a point where I got something really substantial running yet - I think I will get there over the next weeks/months, though.

I feel that having someone to bounce ideas off of occasionally would be very helpful (this forum has already been very helpful). Obviously, I’d be happy to provide input regarding their challenges in return. From what I read about “Mastermind” groups, this is what happens there.

I currently pretty much live in a vacuum - I google everything I need to know to proceed building things, I read a lot (online and books), and I try to make up my own mind based on all this. I made a bunch of bad choices and/or needed more time than reasonable because of this.

This weekend I went to a Startup Weekend event and I actually met someone who is already bootstrapping their business (but not making a lot of money yet). I also had the opportunity to try to help a bunch of people and that might develop into a mentoring relationship - if they have enough drive to pursue their idea until it works.

If you want to help people, I think going to a Startup Weekend is a fun way to do it. It’s definitely not all crazy people who want to do a “startup” there.

That’s awesome. Sounds like a great idea! Thanks @grumpi

You know, how about instead of mentoring an ‘apprentice’ we try to help each others as entrepreneurs? I mean, each of us has different strengths, weaknesses and expertise, we can be both mentors and apprentices. Like a hands-on club, entrepreneurs helping entrepreneurs, not just motivational advice but with solutions for actual defined problems (business, marketing, growth, technical, design etc). Personally, I have a lot of experience server side (over a decade developing web apps) and I can help with scalability, architecture or coding problems.

If you’re into gaming, let’s make a guild :smile: The “novice entrepreneurs” or something like that. What do you say?

I currently pretty much live in a vacuum - I google everything I need to know to proceed building things, I read a lot (online and books), and I try to make up my own mind based on all this. I made a bunch of bad choices and/or needed more time than reasonable because of this.

@grumpi Wow, I like that I’m not the only one… :slight_smile:

Somehow I must have missed this post. :smile:

If you’re into gaming, let’s make a guild The “novice entrepreneurs” or something like that. What do you say?

Read a bit from your blog. You really sound a bit like me (yes, I had a phase where I started/romanticized building a strategy MMO, too) - except that you have a good deal more technical experience. I can totally relate to the feeling of “having to build something first, then promote it”.

I’m in for pushing you towards acquiring those marketing / copy writing skills that will help you get people on your site. It’s not that I know a lot about it but I know that there’s something magical to mirroring the feelings of your customers (or children, for that matter). I think I could learn copy writing. I enjoy pushing people towards working on their goals - sometimes it’s so much easier from a distance to see what could be done in order to make progress.

So, where could a guild like that hang out? :wink:

Ya that could work. I think that’s generally what masterminds are for. But maybe you have something a little different in mind - more of a co-op than just a discussion/accountability group.

Maybe we can chat one of these days.

more of a co-op than just a discussion/accountability group.
More or less. I’m aiming for a group where we can talk about actual problem and solutions, based on participants’ experience/expertise . I must say it’s pretty vague for me,too.

So, where could a guild like that hang out?
@grumpi I have no idea, this forum, slack? Our very own sub reddit ?