Milton is a consultancy that focuses on early stage sales and marketing advising, typically from seed stage up through around $20mm in revenue. I engage with companies that have some sales traction but are looking to improve their process, revenue growth, pitch and deck, or hiring processes. The vast majority of sales roles are in companies where there's a well-defined product market fit, a supportive marketing org, and a roster of existing customers. Before all of that, when things are basically pretty chaotic and definitely not well-oiled, when the sales process is mostly founder-led, and when there isn't a page with dozens of customer logos...that's where I find the most joy - and consequently where I help companies the most. Some sample recent clients from across industries: ArtisanAI, Ascend Insurance, Default.com, Eppo, Daydream, Forge, Inductive Bio, Mandolin, Monte Carlo, Orb, Tonic, Savvy Wealth, UnifyGTM, Valdera, Wing Security.I also make furniture :)

Stopped working for companies and focused entirely on some other pursuits, mainly woodworking, spiritual study, and being with my young kids. Built out a woodshop where I made low-quality furniture at a glacial pace, an utterly non-sustainable business model but one that provided me ample time to rest and reflect, a period that was one of the great inner experiences of my life.As a professional extrovert for ~10 years before this time off, it was very nice to spend long, sustained amounts of time alone with my thoughts (and a comprehensive playlist of French reggae) while making sawdust.I did advise startups during this time (as I had been doing for some years already), and came to realize that the early stage, $0 to 10mm in revenue challenges were interesting, intuitive and fun for me, and that I could slip into "flow state" in those engagements as much as I did in woodworking. Decided to devote more time to this type of work.

Joined another small team, less because I knew anything about insurance and more because I loved the founders, the team, and because nothing makes me feel more alive than tackling something wildly new. I think that's because it's fun to learn and figure things out quickly and also it's because when the expectation of failure is high, I feel much less constrained by the weight of expectations and past achievements. Once again, built a business from something quite small to something quite large (and going strong), but in retrospect feel most pride for the shared wins, the crushing of numbers, and the dizzyingly steep climb up new learning curves. This time, with the benefit of hindsight, I knew that working at a big company wasn't my cup of tea. When we completed a merger that brought us to 700 employees and I took the opportunity to retire!

Tech for Campaigns is just a flat-out wonderful organization. Took a full-time volunteer role in 2018 to help out with the mid-term elections because, I'll say it, I hate Trump and wanted to help blunt his agenda (gasp!).So proud of the good work done by our teams across the US.If you're considering volunteering (or working full-time) for Tech for Campaigns, I'd highly recommend it.

Joined Segment as the first employee when it was 4 college drop-outs working out of an apartment. Thought it'd be fun to try a much smaller startup, the guys seemed nice (if clueless), and they offered me the title of "director", though I had no one to direct but myself.I had no idea what the product did because they were too techy (and I was too tech-illiterate) to understand any of their explanations. But eventually I figured out what the heck the product was, and then I figured out how to sell and market it. In short, we built a very big and very successful company together which sold for a bunch of money.As I look back on my time there now, the things that make me particularly proud was the culture that we built, the quality of the people we hired, the career growth that we fostered, and the spirit of entrepreneurship that we fostered which has, in turn, spun out countless new startups by Segment alumni.Ultimately I left when the company reached the size where leadership was about people management. That is not my sweet spot and I don't think that I'm particularly good at it either!

For two months my resume was rejected out of hand by every tech firm I applied to. Then I discovered a company scaling its sales team so fast that they were resorting to an open bar as a way to mass interview prospective employees. Seizing my first actual shot to interview, I went to the bar, pounded drinks, and came away with an entry-level sales job.I quickly discovered that sales was a *good* fit for my personality, and that tech startups were a *perfect* fit for my personality. I loved the culture and camaraderie, and the spirit of common purpose that exists in the world of tech startups and which was the direct antithesis of work at a large law firm.Kontagent was not a successful startup for many reasons, but experiencing that failure was immensely valuable. I learned so much about what separates healthy companies from unhealthy ones and as it came time for me to build companies I was able to avoid a bunch of pretty easy-to-make mistakes (e.g. don't conduct interviews at an open bar). In the end, I cherish the experience.

While working at the law firm, I wondered if I could ever return to my normal self, and if so, how long it'd take to wash the stink of BigLaw out of me. Luckily enough, I discovered the answer: a bit under two years, and several thousand miles of bicycling.Left the law firm, bought two bicycles and an engagement ring and set off around the world with my (now) wife. Learned Spanish, Indonesian, and spent meaningful, open-ended time in about a dozen countries.Thoroughly de-programmed myself from my law firm days, and let myself drift towards an open-ended curiosity and enthusiasm for what life might have in store for me. Also got into some knife-fights in Central America while fighting off armed robbers that weren't especially fun.Returned to America and, at the urging of my then-fiancee, decided to move to San Francisco to see what that city had to offer.

Like most, I came out of law school with law school debt. And so I followed the rest of my class into "Big Law" which offered little meaning, purpose, free time, or opportunities for personal growth, but did provide one the means to cut down that debt fairly quickly. So for three years I worked like a dog, lived like a monk, and saved every penny I could.The paid work I did was on private equity M&A and securities litigation, with a bit of white collar defense. But the much harder work that I did was to keep my head up and remember that there was more out there in the world than billing in 6 minute increments.My advice to anyone thinking about a career in Big Law is to really examine their motivations and get a deep feel for whether that lifestyle matches their motivations. DM me if you're on the fence about law school and want to get a perspective.

One of the few, glittering examples of meaningful competence within Africa's most populous country has been their ministry responsible for telecom law and development. I was invited, due to my work the year before, to go to Nigeria to do some consulting work for them while on break from law school.I'm sure that my meager efforts were not particularly useful, but I did have a very nice time traveling around.

This was a very cool grad school project. Prof. Leslye Obiora and I went to Nigeria to co-organize a conference focusing on developing a philanthropic sector within the country (by tying regulatory/statutory frameworks to indigenous cultural practices of giving). It turned out to be an astonishingly big deal (thanks entirely to Leslye). But the net net of our success was that two weeks after the conference, the President of Nigeria asked her to become the Minister of, effectively, natural resources.I flew around Nigeria on government jets with Leslye, but this was summer break from law school and I wanted to do something a bit more hands on. So I returned to a village where I helped set up a literacy/numeracy program for adult/youth education with an integrated microfinance facility.A wonderful summer and a wonderful experience.

I founded a non-profit organization that focused on women's rights and anti-human trafficking. Men typically think of women's rights the way they think of women's health, which is not really focused on them, but men have a critical role and responsibility worldwide to learn and act on the issues that face women because many of those issues are caused by men.I rode a bicycle across the USA, teaching in high schools along the way about these issues. I then rode through Southeast Asia, meeting with anti-trafficking organizations. Got a Ford Foundation grant (thanks!), a bunch of corporate sponsorships and press coverage (thanks!), and met some truly incredible and inspiring people. Hopefully, I helped change a few perspectives too.This was project based, so the work ended at the end of the ride, which was 36 hours before I started grad school.