I think the attitude might be a big problem. I wasn't able to understand anything from the sexiest mansplaning viewpoint.  the only detail you gave what he gives bikes away for free. otherwise everything else was dismissed from his conversation to you, when you then wrote it to us.
so start off with the details of what he thinks is a good reason to give bikes away for free.
now for your point of view I agree with you that earning a bike is very important versus getting a bike for free. People take care of things they earn and they are less careful with things they don't earn.
I also agree it builds community. I disagree that is more sustainable a good business plan is what makes either of these programs sustainable or Crash and Burn. I disagree that earning a bike makes you more safe you have safety education as a component of the training. Earning a bike on its own does not necessarily make you safer as a cyclist.
and you are correct learning to work on your own bike while earning a bike is empowering to the cyclist.
Now spend some time listening to the mansplaining. And tell us what he thinks is Right rather than just dismiss him out of hand. Second youth is not a reason to feel you have no persuasive power of communication. And I understand that there is sexism out there in both directions. Listen to understand not to just be submissive. Speak to be understood clearly not to just talk or lecture. 
I do wish you the best of luck . I think you have the start of good ideas
--------- Original Message ---------
Subject: [TheThinkTank] Bike Collective VS. Simply giving away bikes
From: "Sylvie Baele" <sylvgrb@gmail.com>
Date: 7/2/18 8:13 am
To: thethinktank@lists.bikecollectives.org

Alright friends, I am reaching out for some resources.. I have a meeting soon with a guy who has an organization which gives away bikes. "Second Chance Bikes"
Now, I don't disagree with giving people bikes... but I think the bike collective model (like earn-a-bike) is more empowering and sustainable long-term. And of course encourages safer riding, all while building community... 
Got any resources  (or data) that can help support my/our position? I am a bit nervous as my meeting is with an older white male and I'm a younger female. He's already mansplained me once before.
Sylvie Baele
"I am more and more convinced that our happiness or unhappiness depends more on the way we meet the events of life than on the nature of those events themselves." - Alexander von Humbolt
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