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
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 )