I am going to consolidate
1) Would you mind telling us what region you are in/if you stayed in NYC? If you left, how did you decide where to go?
I am from Philly so I am back in Philly. I have a couple of matters in NYC still, I am actively thinking about expanding in NYC. But NYC is competitive, too many lawyers... I am somewhat of a commodity here in Philly as a solo.
2) What would you do in hindsight if you were to do it again (preparatory steps, etc.)?
Spend more time getting to know more people in school. We had kids, one was born while I was in law school, so it was a bit hard to meet people. I did a decent amount of networking while I was at the firm, but time is limited, and also hard to network in Philly from NYC.
3) How much savings would you recommend/do you need to launch a solo office properly?
A year of living expenses. I didn't quite have that much, which makes me more nervous than needed. Having a bigger cushion definitely helps calm your nerves. But then again I work better under pressure...
4) Do you advertise? Why/why not?
I am very good at marketing due to what I did before law school. I advertise to my different streams differently:
4)(a) how do you get tech clients:
I took an office space in a co-working space full of startup/independent developers. It took a while to get noticed, but it is now slowly starting to generate returns. Also a private office in a co-working space (which is very modern and good amenitities) is much more money for the buck, it looks pretty great to my non-tech clients.
4)(b) I speak a foreign language, so I advertise in a foreign language news paper. I have a quarter to half page ad in it. It generates (based on my anecdotal knowledge) above average leads. It took a couple of months for people to trust a new ad, but now that it's running for 4 months, the volume has been decent.
5) Did you find your biglaw experience to be helpful to what you do now?
Yes, I was trained to do everything right. It is a certain level of professionalism that my non-biglaw friends don't know or appreciate. And in turn my client knows the difference between me and another solo. That allows me to charge much more (not everyone pays but I don't budge).
6) Apart from the previous question, do client's care whether you came from biglaw/what you did there/your experience level, etc.?
Yes and no. Smaller matters, things of personal nature, people don't really care. They probably care more about where I went to school. Business and more sophisticated matters yes. First, ex biglaw attorneys generally understand how corporations work. So when a potential client chat you up on general corporate matters/issues you are not out of your element. Second, people with high value work do really appreciate and understand the biglaw quality, and they appreciate getting it at a lower rate because of my low overhead.
I have a potential client right now who told me they went to a few small firms before me, but I stand out because of my school and biglaw experience and they are more comfortable with me understanding their business.
7) Who would you say is your core client base and how do you get in front of them?
Small business and startups. I do free workshops, I own a meetup group, I reach out to different non-profits. Get to know people, let them know what I do and they will understand why I am more suited to help them with their business related issues than any other solo lawyer they know.
8 ) What do you think separates people like you (who are successful launching a solo practice) vs. those who are not successful?
Don't call me a success yet, I am just starting. But I have successfully (and unsuccessfully) ran startups and small businesses before. There is a much lower hurdle of entry for me to enter solo practice, and I also understand my clients perfectly well (because I was one of them before law school).
9) When is the best time to go solo/leave biglaw for solo practice?
When you are ready?

There is usually a skill gap between junior and mid and senior associate. I was already communicating with opposing counsel and managing some discovery tasks when I left. I felt that I would not get much different experience for the next few years, so why grind it out. The money is what's hard to give up, but if I did what I think I could do, I can make similar level of money without grinding so hard. As I just came in today at 10:30 wearing shorts and a polo (no client meeting today), I think I made the right choice.
10) Why did you decide to leave and was there a catalyst that made you take the leap?
See all the above. But at the core, I really wanted to do more in my client service. I think it would be satisfying for a biglaw partner or senior associate to avert a disaster for a large client, it really would be cool, but I was nowhere near that. At the same time, I start to come across smaller potential clients I could help but not as a biglaw associate. I wanted to accomplish more, and I know I had what it takes to generate business.