Skip to Content

Alex Hillman

better coworking, better business, and better communities

Twitter Instagram

Search this Site

Type in terms like retention, culture, or tummling and press enter to search.

If you can’t find what you’re looking for by searching, don’t give up! Shoot me a message on Twitter, I might be able to point you to a post about the thing you’re looking for.

How did I get here?

17 minute read
by Alex Hillman

If a “career” is the sum of the activities which make up a person’s work history and future, mine is unorthodox, to say the least.

My first career choice (age 7) was to be a paleontologist. Then I saw Jurassic Park and realized how dangerous it could be. Scratch that.

My second career choice (age 11) was to be a professional magician. Then I saw David Copperfield (a bar mitzvah present) and realized how creepy he was. Scratch that.


By the time I was 15 I had figured out how to take apart a computer and broken the family PC enough times that my dad made me responsible for getting it working again. I walked into a local neighborhood computer shop (remember those?) to buy a new motherboard. The shop owner asked me, the 15 year old me, “so what are you going to do with a motherboard?”. I told him exactly what I was going to do with a motherboard and he offered me a job after school to learn how to build computers. The owner and the lead repair tech taught me hardware and software diagnostics. I worked my way through high school and even some time in summers after college at the computer shop. I solidified my passion for technology. My boss asked me “so when are you going to learn to write code?”. I told him I wasn’t interested in being a code monkey, diagnostics were what thrilled me.


So I went to Drexel for a business degree. I thought, “I’ll learn to run a business, start an IT diagnostics firm, and make a mint”. I had a great time at Drexel, much to the chagrin of my grades and subsequently my scholarships. It’s ok, though, because I wasn’t excited by what I was learning. But I stuck it out for the co-op program that Drexel is known for. I’d get an awesome job, learn what I wanted on the job, and then graduate to start my company.

My first co-op working with technology in a corporate business setting was working for a bank. And firmly decided that I did NOT want to start an IT consulting firm, because I’ve never been so bored in my life.


For my 2nd co-op, I had a friend who had been working at a local interactive agency. His job sounded fun. DVD rental library, razor scooters, fun client brands I’d actually heard of. But he was a coder. And I’d told my boss back at the computer shop that I didn’t want to be a coder.

But I thought, “what the hell”. It was a 6 months, no strings attached attempt at a career that I had no experience in, and only assumed that I wouldn’t enjoy.

I actually told them that when I went for my interview.

Now, here’s a fun anecdote: I was interviewing for a position as a front end developer. The practical test I had to take involved basic HTML skills, like taking a sliced up image and putting it back together with a table. After all, it was 2004 and CSS based layouts were just barely beginning to be adopted. I still tested in Netscape, and IE 5.2 for Mac.

But at the time, I didn’t really know any HTML. So I snuck a preview copy of the exam and did my best to memorize the answers.

I knew I could learn quickly anyway, and the answers would always be at my fingertips on HTMLdog.

So I passed the exam (technically cheated), and was offered and accepted my 2nd Drexel co-op as a web developer.

I fell in love with web development. My manager was awesome. My mentor was incredible. My coworkers were rad as hell, and our CEO was a quiet visionary. I absolutely loved this job, and I loved this industry. I made incredible friends whom I still am in touch with today, though many I wish I saw more often. I was introduced to names like Zeldman and Meyer and PPK. People who continue to walk in my pantheon today. And even some who I’ve come to consider friends.

This job changed my life. I didn’t want to be a coder, I wanted to be a developer. I wanted to creatively express technology. I loved having tools to artistically create, where I didn’t need to be a designer. I could make beautiful things that real people actually use and saw.


When my 6 months was up, I went to my department manager and told him I didn’t want to go back to school, I love my job too much. I was learning more on the job, and having more fun, and making money. Why would I give that up?

He made me promise that I’d go back to school, since he was a dropout himself who was JUST finishing his degree in his early 30s. I obliged, and he let me stay past my co-op.

As this company swelled, and went through some severe growing pains in terms of culture and leadership, I found myself without a job (Not for lack of trying on my manager’s part. They did everything they could to save me a seat at the table). Luckily, there was another group of people that I’d worked with who had also left, but to start their own company. So I rang them, let them know I was on the market, and they offered me work on the spot.

I started taking some night classes to follow through on my promise to my former boss, but was quickly frustrated. I’d grown accustomed to work that actually had value, and classwork wasn’t doing that for me. I’d grown accustomed to working well in teams, and my classmates were not good at that at all. And I’d learned about some of the most progressive technology, which is not even CLOSE to what Drexel was teaching.

I gave up on the degree and it’s value. Drexel had given me what I wanted: an opportunity to try something that I wouldn’t have otherwise. If it weren’t for that 6 months, no strings attached gig, I wouldn’t have fallen in love with the internet. I wouldn’t know HTML.


I filled that time I had been in class after work with some freelance. I was a pretty solid front end dev, and had a good enough network of people who’d spun out from that original company that I had plenty of work to supplement my income, keep me busy, and push me to learn more. On top of learning how to be a better coder, I learned project management skills, sales skills, and the business skills that I’d hoped to learn at Drexel but didn’t.

As I tasted more, I wanted more. I went to my boss and told him I wanted more opportunity to lead.

He agreed to it. Then he strung me along for nearly 6 months, through one of the most interesting (and also most infuriating) projects I’ve ever built. And my frustration with not having an opportunity to lead grew into resentment.

I left that company, and not on admirable terms. I’m sorry for that.

I did, however, take to freelance. I’d built up a strong enough network and a couple of key contacts that had more than enough work to pay my rent and put food on my table.

And as I worked on more projects, I had more opportunities to bring projects to the table as the lead. I had acquired the client, I led the project scope, vision, etc. I sucked at it at first, but I got better quickly, largely because I was learning from the other people who I collaborated with (many of whom I met back at that first interactive job).

Coworking & Chaos

I was also learning about coworking, and saw that as an extension of the way I was already working. It also seemed like a part of the solution for some of the things that I felt were missing in Philadelphia.

I learned about it from a duo who were unorthodox themselves, individually and together. They did more than just teach me about coworking, though, they taught me about a whole other ecosystem of frameworks and events for “getting things done”. Through them, I learned what it meant to “embrace the chaos” as a leadership model.

Indy Hall

I started sharing the idea of coworking with places that I saw people having interesting conversations, but realized how the 80/20 rule really worked: 80% of the people talked, 20% did anything. Luckily, that 20% yielded some of my closest friends and colleagues today. With the partnership and guidance of Geoff DiMasi, I led Indy Hall into fruition, from a nascent community of a handful of nerds to one of the most incredible, diverse, and powerful groups I’ve ever been a part of.

The things I’ve learned about leadership from Geoff are too numerous to list here. But know he’s had an immense impact on my worldview and leadership style, and I’m thankful. Indy Hall has been a vehicle for many things, not the least of which was that learning and personal growth.

At Indy Hall I found myself surrounded by even more leaders. Real leaders. People who had vision, and didn’t just tell you how things would go, but they actually architected the world and experiences around them. We continued to teach each other through our experiences, successes and failures.


I’ve always loved throwing parties. The same activity that probably did the most damage to my grades and scholarship provided the most powerful mechanism for changing the world around me. I’ve thrown more parties than I can count in my professional career, and in all of them, have made connections that I firmly believe have strengthened my place in Philadelphia, in my career, and in life. Learning to lead social interactions, which ultimately is raw relationship building, is one of my hugest assets.

Also, I have a neighborhood bar that’s cooler than yours. I gua-ran-tee it.


Indy Hall has been a labor of love. I’ve poured countless hours into it, consciously and not. It’s not a venture I created to make millions from, though that’s not to say I still can’t. But the value it’s provided me has been immense. I’ve learned about running a business. I’ve learned how other people run their businesses. I’ve learned the ups and downs of widespread attention. I’ve hired and I’ve fired.

But while I wasn’t growing Indy Hall for the sake of growing a business, my palate had been whet for the taste of building businesses and the mechanisms that run them. People were interested in “my way” of doing things, and I began finding myself doing less web development and more business consulting.


At the end of 2008, I came up with the idea for as a way to hone those business consulting skills, but work with people I really thought I could help. So starting small made sense. I also ran a weekly video stream for a while where a group of people helped each other. It was like going to group therapy for business. never made me a ton of money either, but it did become a placeholder for opportunities to come and a great way to weed out people who wanted free advice. I’ve heard anecdotal stories about some of those “ Live” sessions helping people make decisions that they are very glad they made. Even if one of those stories is true, it was worth it.


I’ve fallen out of love with the word “entrepreneur”. It is crusted with hype, and tends to be a self-assigned descriptor more than anything else. I’ve sometimes been pinned with this label, by virtue of the fact that I’ve largely paved my own way for the last few years (and started a business or two). But I don’t think of myself as an entrepreneur, or any of the things that supposedly come along with it.

There are qualities of “entrepreneurship” that are undeniably valuable as part of an ecosystem, and importent to overall progress as a society. But I’m more interested in those individual qualities than some arbitrary mashup that’s been given a label.

I’d rather think of myself as someone who works hard at what they think is right, than someone who won’t be proven wrong.

I’d rather think of myself as someone who pays attention to the world around them, rather than constantly sniffing for opportunity.

I’d rather think of myself as someone who want’s to make a difference, rather than someone who wants to make something different.

I’d rather think of myself as a cautious optimist than a forced realist.

I’d rather build businesses that create value than reward ideas with no intrinsic value whatsoever.

“Entrepreneurship”, as far as I’m concerned, is a merit badge in the boy scouts.

So I press on.

Back to the FutureAgency

As the summer of 2009 came to a close, I was wrapping up some web development projects and feeling the need to start in on something fresh and new. I went to dinner with my friend and and mentioned I was looking for my “Next Big Thing™”. She is the VP of Social Media something or other at a well known advertising agency in Philadelphia. I’d always admired their creative work, and knew that she loved working there. She suggested that I talk to their co-founder and CCO. I explained that I wasn’t looking for a J-O-B. She urged me to meet with him anyway.

We talked about a number of things, but one of the important recurring themes that came up was their desire to re-invent their interactive team and practice so that it wasn’t dependent on a single leader…but rather a team of leaders, well integrated into the rest of their creative process. And so, among other things, I joined with the opportunity to craft just that.

I spent a year (exactly) with that agency, and with the support of their leadership team built their interactive group into one of the strongest and most dynamic teams they’d ever had. We didn’t get to accomplish 100% of the goals I set out to do, but we made what I believe is incredible progress, and I’m confident that the team is capable of taking them through the next year and beyond.

Everybody Wears T-Shirts

In the middle of that year with the agency, another opportunity arose. For almost as long as Indy Hall had been open, I’d had a consulting gig with a local, medium sized, family owned, t-shirt company for a couple of years on it’s B2C business, in a variety of different capacities (literally, from writing code to inventing marketing ideas to digging into business process to providing corporate therapy to the CEO). I learned how a business that depends on physical inventory works (and how much it can suck), but also how a business with global reach and a passionate focus on great customer service can really run.

Earlier this year, I sat down with the CEO and Chairman of that company (a father and son duo who I’d grown to love like family). I suggested that my work with them was starting to become challenging, because we consistently ran into problems that the company simply didn’t have access to the technology ready to support our ideas, regardless of if the ideas were good or bad. I suggested that the company lacked a CTO, or a Director of Technology. My recommendation to hire someone in-house who could “own” the knowledge of their systems and find the best ways to use the technology they did have to make some forward progress on our ideas, and I’d continue to consult to make sure that the technology continued to support the business in ways that I’d spent all of that time helping them dig into. I was 100% not expecting their response.


Rather than hire a CTO for me to work with, they hired me.

And for the last 6 months, I’ve been their Director of Technology (or whatever my title is).

I’m not quite sure if I knew what it meant to be a CTO (or any C-level employee), even though I did write the job description that they were so firmly convinced described me. I knew what the role should be capable of. And sure, I had ideas of how I would do it, but it wasn’t until I was in the thick of it that I understood what it meant to be a Director.

It’s not about the title. Or the salary. Or the benefits. Or the potential power trip. Or the company jet (psych).

It’s about being a directing. Guiding. Finding and defining a vision, gathering buy in, and then orchestrating the pieces together. A bunch of instruments playing aren’t a symphony, they require a conductor to keep them all in pace and aware of each other. And so does a director.


“Director” is often synonymous with “final say”, and I think that my experiences in learned leadership and the mentors I’ve had kept me from making it about that. My say wasn’t nearly as important as whatever vision we’d all bought in on. If someone else’s idea supported it better than mine, we went with theirs.

I said “no” a lot in the last 6 months, too, but not because I didn’t want to do things. Because they weren’t aligned with the vision we’d all bought into.

And so, after guiding a team of  12+ through one of the largest (if not THE largest) technology initiative I’ve ever experienced (let alone led), I’m confident that I’m onto something with my preferred techniques for directing a project, for guiding a team, and for communicating the rhythms of business.

Directors primarily work with people, but the number one tool in their arsenal (apart of great communication skills) is the ability to pick a direction.

Direction. You can only go one of them at a time, but you don’t have to go the same one forever.

Try to pick a good one.

This post is dedicated to the countless people whose journeys I’ve woven mine with over my last 27 years on this planet. Thank you for having an impact on me, even if I haven’t been able to figure out what it was yet.

This will help make sure you can find the most useful resources. I respect your privacy & email. Absolutely no spam, and I won't ever share your data. Pinky promise! 🤞

Hey, thanks for reading!

Alex Hillman I am always thinking about the intersection of people, relationships, trust and business. I founded Indy Hall in 2006, making us one of oldest fully independent coworking communities in the world. This site is packed with the lessons and examples I’ve learned along the way. You can find me on Twitter, too! 🐦 Say hi.