Jeremy, it wasn’t such a risk, since I got lucky with my timing.

In early 1995 I left Charles Schwab, where I’d been evangelizing the Internet, telling people that e-commerce, including brokerage work, would migrate to the Net. This was based, in the short term, in working with an unrecognized guy (Darius Milewski) showing me the earliest Web technology, the NCSA server and the first graphic browser.

That built on my nerdy tendency to read science fiction, which, seriously, prepared me for the changes that the Internet would facilitate. (This is a real “paradigm change”, leading right now to a major “power shift”; apologies for using outdated business cliches.)

My first real gig was helping build the Bank of America site HomeBanking, while running craigslist by myself, as a hobby.

After two years, Silicon Valley job posters were asking to pay me to post jobs, and I just followed through.

The biggest risk taken: in ‘99, when I had to make craigslist into a real company, I declined the usual industry thing to take a huge amount of money, deciding that I know when enough is enough. Seriously, no one needs a billion dollars.

Well, decide if you want to build something which is cool or something which is useful. Sure, you can do both, but I’d suggest the useful part.

Start building your own branding and identity, both for you and as an individual. You’re responsible for your own reputation, which is as important as what you create. Plan for worst-case scenarios if you get traction, when bad actors might attack via unscrupulous media.

Treat people like you want to be treated.

Levi, social media is just about how people talk to each other, it’s getting greater and greater usage, and becoming the usual thing for everyone everywhere, over time. Some media tools will continue to be big, or maybe fade away, and new ones appear that might appeal to particular groups.

I figure find ones that feel right to you, and use them, to connect with people socially and professionally, and then, I’d like you to use social media to support the causes that matter to you. Like maybe you can use social media to support veterans and military families.

The most valuable skills vets possess are the most difficult to articulate to civilians, including even myself. Those include:

- attitude and ability to get stuff done
- situational awareness
- ability to articulate a cogent sitrep
- fast adaptation to changing circumstances

There’s more, but these are major vets’ skills that are really valuable in business that are hard to communicate with a civilian hiring manager.

The problem is the civilian-military cultural divide, and it’s really bad in hiring, since civilians aren’t trained to understand military culture, and vets aren’t trained in civilian life. (I’m quietly pushing DoD to do a better job in the Transition Assistance Program, but change is slow.)

A hiring manager will usually want to give a vet a break, but won’t understand what a military résumé will be talking about. (Also working on that with DoD TAP and other efforts, but little progress.)

I’d recommend a frank discussion with the hiring manager about the skills that I list above and ask the manager to help you translate that into the language and culture of his or her company. That’s extra work for him or her, but I feel it’s okay to ask. You can blame me for the extra time required.

In early years, where I handled it myself, it was building a tough skin.

This is part of customer service, and in such a position you get no respect and a lot of abuse, earned or otherwise. Dealing with that abuse is hard.

(I do lightweight customer service only these days, fifteen or so years of intense customer service is enough.)

I’d build something useful, maybe cool, but focus on useful.

Take responsibility for your individual and team branding, identity, and reputation since that will largely determine if people want to work with you.

Talk to lawyers and tax people from the beginning, there’s a lot of trouble in law and taxes that could become a very ugly surprise.

Christianah, I’m not so good in this area, but… Sharing economy jobs might offer you the best opportunity to make some cash in a way that suits your needs.

For example, Uber’s hiring a lot of vets. I talk to a lot of drivers, many of whom are building their own startups, and it’s working for them. Also, the networking might be really valuable. In one case, I’ve asked for a résumé from a programmer, or, I decided the use of emerging services from a coupla drivers.

Dave, there’s a lot of people who want to do the same thing you do, and the only response is to do high quality, meaningful interaction with people in social media.

Provide useful stuff for people and be generous with ‘em.

Role models include Gary Vanderchuk, Guy Kawasaki, Marcia Collier, and Sean Gardner.

Steven, I got lucky, since I ran my thing for a few years for fun, spending little money… and then people asked me to let them pay me. So, I’m not good at this one.

However, the use of crowdfunding, like Kickstarter or Indiegogo, work for a lot of people. The key is organizational realism and discipline. Planning a new product requires that you’re realistic about what it takes to make something new, and the discipline to do actual manufacturing. In particular, outsourcing is harder than you think.

Patrick, I’d suggest you do it. In particular, I’d suggest that any vet do so, due to the civilian/military cultural gap. It’s really hard for your manager to cross that gap, he or she will be reluctant to do so, and it’s up to you.

If that’s awkward in any manner, blame me.

Treat people like you want to be treated.

BLUF: bottom line up front; get to the point, or “brevity’s the soul of wit.”

(I figure you know that better than me.)

Caleb, it has to do with the civilian/military cultural divide that I talked about above. Civilians and vets don’t really know how to talk with each other when it comes to job culture.

I’d talk to local and national VSOs to get a hand with that, even go to networking events put on by companies. IAVA can help, and VetsInTech is really good to get vets to tech companies.

Also, I’d go for interviews and tell the hiring manager that you’ll need her or his help making sense of military skills in civilian job terms. Ask for a little extra time, and if he or she balks, tell ‘em I said it’s okay.

This is really hard, since people are always looking for the great new idea, so there’s a lot of competition for any potentially saleable scrap of novelty.

I’d suggest looking at the way you work, and then, figure out how it could be done better. You might not be the only person who needs something to work better, and your solution might be marketable.

Eric, I got lucky.

I’m a nerd, and after running the company for a year, people helped me understand that as a manager, I suck.

Fortunately, I’d already hired a good guy who had more natural management skills than I had, and then I delegated it all to him.

The lesson is to admit to oneself one’s shortcomings, and to get outta the way as necessary.

Michael, this reflects some of the advice previously given, citing the cultural divide between vets and civilians.

I can suggest that if you sense a combination of possible job fit, and convenience, ask the hiring manager to bring you in for an informational interview. If it feels right, ask for a little coaching and also for a civilian style update to your resume.

(Maybe I should ask all American hiring managers to do this, now and then.)

Mark, I don’t have a really good suggestion, except find a way to hang out in a coworking, collaborative work space, where the approach is flexible and agile.

In NYC, I’m offering scholarships to vets for a new civic tech space called Civic Hall. Small program, but it’s a start.