I am thrilled to welcome Jesse Middleton to the Flybridge family. Jesse is joining us as a General Partner to help lead our NYC office.  This hire is a big deal for us.  Jesse is the first General Partner we’ve hired in over a decade.  Jesse is a tremendous entrepreneur and executive, having for over the last five years been a part of the creation of one of the most successful start ups in history – WeWork – and serving as an active angel investor in NYC.

Here’s his blog post announcing his arrival:

My venture into venture (capital)

In February I took a look at my journey into the angel investment world. I had been doing it for only a little over a year, but I learned a ton. I learned that I loved discovering and getting to know new founders. I learned that I enjoyed helping to solve some of the earliest challenges that those founders face. I learned that I had the ability to celebrate with the people I backed when they had huge wins and, more importantly, I learned I could be a shoulder to lean on when things (often) didn’t go as well. But my biggest takeaway was a personal reflection: that I wanted to focus on investing in and supporting these amazing founders full time.

These last five and half years helping build WeWork have been a wild journey and I’ve loved every second of it. I got to experience the earliest days of startup life when we all came together at 3am to put the final touches on our first WeWork buildings. I also got to experience the meteoric growth and success as we barreled past 1000 employees and announced our 29th city. Thank you to everyone at WeWork for every single moment. But, as I announced in May, it was time for me to leave WeWork and become a full-time, professional investor.

Today I get to share the next big step of my adventure — I’m joining Flybridge Capital Partners as a General Partner. I will be leading our New York office alongside the one and only David Aronoff. I couldn’t be more excited to be a part of the Flybridge team!

David and I met five years ago at a Flybridge event. We became fast friends and I’ve been able to look to him for guidance and mentorship (and he’s always up for a drink) ever since. I met the Boston team a few years ago when I helped launch WeWork Boston and have loved our interactions as well. Flybridge has had a strong presence in New York for years. David opened the office here four years ago and the partners have invested in some amazing companies including 33Across, BetterCloud, Bowery, Codecademy, MongoDB, NS1, Raden, Shine and tracx. With my arrival, we plan to support our “family” of portfolio companies here even more while also doubling down on investing in the New York City startup ecosystem.

When I first sat down with the Flybridge team, we talked about what they were looking for in a new partner and where I wanted to take my journey next. Two things became abundantly clear very quickly:

1. They were great investors, board members and champions of their portfolio companies and their founders.
2. As good as they were at being great investors, they were even better people.

Every single person I talked to throughout the process echoed these two things. As I got to know them better, it quickly became clear that working alongside the whole Flybridge team just felt… right.

WeWork’s mantra is to “Do what you love” and that’s what I know I’m continuing to do now. I’m excited to dive in, to get to know the Flybridge Family (52 active companies and their thousands of employees) and to continue to support the New York community that I love.

If you’re working on something interesting, are looking for feedback on your new idea, thinking about raising your first round or simply want to shoot the shit about startups and NYC over a drink don’t hesitate to say hi. You can reach me at jesse@flybridge.com, on Twitter and on Facebook.

“…a state may, if its citizens choose, serve as a laboratory; and try novel social and economic experiments without risk to the rest of the country.”

• Supreme Court Justice Louis Brandeis, 1932

A few years ago, I was frustrated with the lack of progress on immigration reform out of Washington DC. I brainstormed with an immigration lawyer friend, Jeffrey Goldman, and came up with the idea of the Global EIR program: a public-private partnership where a university could sponsor an H1-B visa for an immigrant entrepreneur, avoiding the onerous lottery system. Last year, we partnered with the state – with the support of the legislature, the governor and the Mass Tech Collaborative – to launch the first global EIR program in Massachusetts in partnership with the University of Massachusetts under the leadership of vice provost Bill Brah. That program is now over one year old and has seen tremendous success thanks to Bill’s indefatigable drive as well as the support of the state and private sponsors SVB, Goodwin Procter and Mayor Bloomberg’s foundation.  Specifically:

• 20 visas issued to immigrant entrepreneurs (100% approved by USCIS)
• 16 companies (most of whom wouldn’t be in the US if not for the program)
• Over 200+ jobs created across those companies
• Over $100 million raised by those companies

In partnership with my friend, Brad Feld, we created the Global EIR Coalition to take the program national and hired Craig Montuori to lead the new non-profit. Brad helped extend the program to Colorado in partnership with the University of CO Boulder.

Earlier this year, New York got into the act, partnering with the CUNY system to launch their version of the Global EIR program. They plan on issuing 80 visas to immigrant entrepreneurs.

And today, I am thrilled to report that both Babson and the University of Alaska have announced that they are launching their own Global EIR programs. Babson is consistently named the top ranked entrepreneurship school in the world and so a bellwether in the field. Alaska is the first West Coast program and has the opportunity to draw from its strong relationships with Asia and Russia.

If you’re interested in learning more about the program, supporting it philanthropically, applying for it, creating it in your home state, or whatever, contact one of the local chapters or get in touch with Craig via the Global EIR Coalition website.

Onward towards rational immigration reform – state by state!

A few months ago, I wrote a blog post warning entrepreneurs that their LTV math was wrong. In other words, their methodology for calculating the lifetime value of a customer was incorrect and, typically, a grossly optimistic figure. It got a lot of attention and even inspired a new module in InsightSquared to help companies do the correct calculation.

In talking about getting these kinds of calculations correct, one of my portfolio company CEOs made an interesting observation to me. We were talking about our customer acquisition costs (CAC), which represents the other side of the unit economics coin. The company is converging on profitability and is thus getting more and more focused on its unit economics and CAC.

“Our historical CAC is obviously irrelevant,” he declared in the board meeting. “All that matters is our marginal CAC.” This struck me as such an important insight that I would try to unpack it a bit because, as with LTV, most entrepreneurs think about their CAC incorrectly.

Many entrepreneurs calculate CAC by simply adding the amount of money they spend on sales and marketing and then dividing it by the number of customers that they have. If last quarter you spent $100,000 in sales and marketing and you acquired 10 customers, your CAC is $10k. A hypothetical consumer company may spend $100,000 in sales and marketing to acquired 50,000 customers to achieve a CAC of $2.

That simple math may be historically accurate but it’s not very helpful as a planning framework. The historical customer count in a consumer company, for example, typically contains customers that came in through a range of sources – paid (e.g., SEM, SEO, Facebook) and unpaid (e.g., organic). Some of these tactics are highly scalable and others are not. Some may even have reverse economies of scale and, thus, actually get worse with scale.

Customer acquisition is a bit like drilling for oil. Sometimes you hit a gusher and it flows beautifully, but eventually that well runs dry and you need to find another one. Similarly, you may come upon a particular customer acquisition tactic and it might be working beautifully and with favorable economics, but eventually it runs its course and you need to deploy another tactic.

That’s where the concept of “marginal CAC” really matters, as my portfolio company CEO wisely observed. When looking ahead, you want to know what the cost is of the next set of customers that you’re trying to acquire. That is, what is the acquisition cost of the marginal customer. If the only tactic you can scale is Facebook ads, then the marginal cost of acquisition of Facebook ads matters more when forecasting your future CAC, not the blended average that you’ve been able to achieve historically.

An e-commerce entrepreneur we were speaking with the other day cited a historical customer acquisition cost of $150. The CEO then projected that those costs would decline with time – a perfectly logical assertion.  As part of our due diligence, we asked for how the numbers broke down by acquisition channel and discovered that the $150 was a blend of organic and paid channels and that the only paid channel that would scale going forward represented an expensive $300 CAC. Thus, their marginal CAC was most likely to be going up over time with scale, not down.

The lesson? As we head into an era of savvier investors who scrutinize unit economics more thoroughly, don’t get caught looking naive when presenting your CAC projections – make sure you’re thinking about marginal costs, not just historical ones.