Start it up

Cityfi
Cityfi
Published in
6 min readFeb 13, 2018

Startups are changing the game in dynamic industries all over the world. This Q/A provides a firsthand look at what it’s like creating and working for a new biz taking a different approach to a traditional business.

When most people think of startups they initially think of technology, open space floor plans or Silicon Valley. But startups are so much more than that. They function as organizations that innovate by trying, failing, and iterating as they reimagine the work that we do, and the environment in which we do it. Startups have been emerging to cater to the diverse needs of people, cities, non-profits, and corporations alike, stimulating new ideas that transform the way we live, work, play and engage, even if we ourselves work day to day in a more traditional environment. With varied work cultures that can function more as collectives than hierarchical organizations, this leaves many people wondering “what is it really like to start a start-up?” Gabe Klein, Co-Founder of CityFi, gives us an inside look at his experience creating, advising and working in startups.

Q How did you and your partners come up with the idea for CityFi?

A One of my partners John Tolva and I had started working on a couple projects together, and I had advised Ashley on the Transportation Technology Strategy for Los Angeles,” Urban Mobility in a Digital Age.” John and I thought the work she was doing was awesome and said — hey, we’re enjoying helping cities post government, why don’t we run with this and see if Ashley would be game to jump in. When thinking about our focus, we didn’t need to be tied to one thing, but rather a multitude of industries, functions, and public and private clients… as cities are becoming less siloed and are emerging as multi-stakeholder ecosystems with a desire to work across many aisles. Collectively, the CityFi team has varied and high level public and private experience, which makes the work we do interesting to cities, start-ups, and corporations. After a year into launching CityFi, we were lucky to recruit Story Bellows to the team to provide expertise in civic innovation and engagement, as well as collaborative implementation models across many sectors. We chart our own course and engage in a range of work including master planning, shared mobility, establishing public-private partnerships, and advising on IoT, big data, and smart cities.

Q As someone who has worked in both the public and private sectors, how is working for a non-traditional startup different?

A I have worked in a lot of startups previously, different types of businesses, and managed small, unruly new businesses. But still, at CityFi I had to get used to contributing within a nationally dispersed management team. Each partner has unique roles, which creates a flat organizational structure that allows us to collaborate and play to our strengths. There is no hierarchy, as within a typical company. Actually, one of our basic tenants when we started the firm was “no assholes” — which simply means we want to work with great people, and alongside great people. If someone is unethical, we reserve the right to not work with them and we choose who we’re going to engage with as clients just as they choose us. The work has to be with people we actually like, and have the same general moral character. That’s one of the greatest things about working for oneself in a startup. Also, side note, you can operate in government as you would in a start-up and there is a formula for it. Shit, I wrote a book about it (laughs).

Q How do you describe CityFi when you first meet someone?

A CityFi is an urban change management firm. But what does that mean? We purposely made it obscure because we want to remain open up to as many opportunities as possible. The work we do is not just limited to cities, we also collaborate on projects in other countries, advise CEOs of publicly traded companies, and advise on strategy in the private sector for funded start-ups and other private companies. Private entities want to know how to work with cities and figure out what they want and need. For instance we may advise on how to realign their organizational structure to reflect a triple bottom line approach to business before we undertake a go-to-market project.

There are many things we can do and it’s less about the industry and function, but how you approach it. This also makes the work we do fun because there is such a wide range of projects that we can engage in, from Compton transit oriented development in LA to mobility planning in West Palm Beach to international work in Asia and Europe. At CityFi we are more doers, and less philosophers. Our clients like us because we have a reputation for getting things done. This is great, but we often find ourselves wishing we could stay for the implementation phase of the project (laughs) because we are used to that level of risk and gratification. Though, the trade off is that you get to work in multiple cities at once, and due to the fact that we work on multiple projects in varying geographies at any given time, there are opportunities for knowledge transfer. So when we are advising, we are also learning, to then share somewhere else. I make a point to listen very intently because I know my next client is going to want to learn from my current client and we may even introduce them. In this way we can cross-pollinate and learn and teach what’s going on in the municipal market for the private sector, and what’s going on in the business community for the public sector and vice versa.

Q What does your day to day look like?

A My day starts at 2pm in the afternoon. Just kidding. I actually built a new office that I don’t even use (laughs). But the office I usually do use is twenty feet from my bedroom with 12 ft X 8 ft glass doors and overlooks the monuments in Washington D.C. Working from home is great, especially when you have young kids and you are on the road ⅓ to ½ the time for clients. There is also a flexibility for working for yourself that allows you unique opportunities, such as travel. I have a friend that is able to work internationally because of this flexibility. The nature of work is certainly changing. While working from home is great, I definitely enjoy getting out of the house for meetings throughout the day (and riding one of my bikes), while also having open time for project work. Because our project range is expansive, we work for people in difference time zones, and I may have 7–9 different types of meetings over the course of the day making our hours flexible as well.

Q What advice do you have for someone starting out in a startup?

A Go easy on yourself. Don’t get too stressed out — which is hard. I have a lot of people come out of planning school, and ask me if they should go work for a city or a corporation, and I say go work for a startup. Simply because, you have to do a bit of everything. Anything from operations, marketing, project support, financing, and how to sell. If you can work successfully in a startup where you are passionate about what they’re doing, that really is the best training for whatever else you decide to take on in the future, including kids (laughs).

CAN’T GET ENOUGH?

Read more about startups here:

What is a Startup?

What It’s Like Working for a Startup

I’m Loving Startup Life After Working for a Big Corporation

Start-Up City by Gabe Klein!

Have a topic you’re geeking out about? Hit us up!

email: alysandra@cityfi.co

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Cityfi
Cityfi
Editor for

Cityfi advises cities, corporations, foundations and start-ups to help catalyze change in a global, complex urban landscape. Twitter: @teamcityfi