Branded VC

Back in March, I published a post highlighting bold marketing, community, and value-add initiatives created by startup investors. I really enjoyed exploring the space, and I continued to follow developments as they happened.

Andreessen Horowitz started a podcast. AngelList launched Funds. RRE backed a Bitcoin lobby. Y Combinator started How to Start a Startup. Collaborative Fund started Alignment Holdings and partnered with Circle Up to fund B Corps.  FirstMark launched its third event series, this one focused on design.  And so much more.

It's tempting to diminish these types of efforts, but I believe they deserve credit. At their core, startup investors provide money. It's the startup teams that build the products and businesses. But investor initiatives serve as a catalyst. They educate, create awareness, affect policy, and bring people together. This is important because it's fueling a startup ecosystem, which is stronger and more vibrant as a result. 

Three weeks ago I created a Twitter account called BrandedVC as a mini side project to surface these types of initiatives—the most creative things happening in startup investing. I think the account might appeal to several different groups, including:

  • Investors: to get informed about and inspired by what their peers (viz. competitors) are doing. This is important because VCs should play offense, not defense in attracting startups and LPs. They shouldn't just rely on the firehose of emails that everyone else is also receiving. 
  • Startups: to discover opportunities, and identify investors that provide value beyond the money that they invest. This is important because founders should do everything they can to help their company succeed, including partnering with the best possible people
  • LPs: to discover investors that differentiate and align with their interests. This is important in an environment where most LPs are unable to invest in the top performing funds.

If Twitter isn't your thing, then feel free to signup for the newsletter below. And of course, if you're aware of anything interesting that I should share through Branded VC, please get in touch at

Branded VC Newsletter

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Officially a Lawyer

On Monday, I officially became a lawyer. Being sworn into the New York State Bar culminates a process that started back in 2007, when I was a Junior in college. At the time, I was starting a company called Concert Footprint. It was to be a community for concert goers. Members would be able to track concerts they attended and wanted to attend, share media captured at these concerts, and connect with likeminded members of the community. 

But the startup world was different back in 2007. Resources were scarce. Mentors and investors were hard to come by. And "Web 2.0" sites were under constant legal threats. Starting Concert Footprint in this environment was hard, especially given the legal uncertainty around hosting a large amount of copyrighted work on the platform. Even standard legal tasks such as company formation, fundraising, and trademark registration were extremely intimidating. 

At the same time, I didn't feel stimulated by the finance and accounting courses I had to take to satisfy my Entrepreneurship major at Boston University. I craved feeling connected to people and seeing my work actually solve problems. The lifeless, hypothetical numbers I tangoed with in class didn't do it for me. 

So I decided to get a law degree. While my passion was always to start a business, I felt that the degree would help me confront the regulatory uncertainties that startups so frequently face. I thought that the degree would give me the confidence to navigate the routine legal issues that businesses, and people, confront in everyday life. And I felt that a law degree would give me the ability to work on the very important issues, both in a business and in other paths of a potential career. I wanted to be involved in the complex Board meetings, the contract negotiations, and the legislation drafting for an issue that I care about. (Of course, you don't need a law degree for many of these things, but it definitely helps with the learning curve). 

Going to law school was intense. Endless study sessions in a law library basement. Impossible attempts at memorizing large bodies of complex law. A deluge of readings and assignments. And then there was studying for the Bar.

I went through all of this as a startup person at heart. There were countless times when I got frustrated by archaic language, inefficient processes, and friction-causing laws. I was surrounded by people focused on a client-centered approach to lawyering; not people wanting a law degree to pursue a career in business. There were definitely times when I questioned whether the law degree was worth it, and whether I should have just started a company and pushed through, or simply joined a team to build other skill sets. And of course, I couldn't help but become a vocal critic of modern legal practice and education—on everything from the exorbitant fees to impractical coursework. 

But I made it work. I pursued roles that blended legal education with technology and startups. I landed positions with TechStars, the White House's Open Government Initiative, and with a respected startup law firm. I did work for ICANN, Pew's Center for the Internet & American Life, Google expert James Grimmelmann, tech law scholar David Johnson, and more. I launched and ran the Law Review's website and digital scholarship initiative. I got deeply involved with Law Without Walls (LWOW), a legal sector innovation program that had just launched at the time. And I came to really appreciate the law—it's undeniable importance in making our society function in which ever direction we take it. 


The ornate, 114-year-old court house where I was sworn in.

It's surreal to finally get to this point and to reflect on all that has happened since. It felt great standing in the 114-year-old court house on Monday, saying an Oath, and realizing that I am now an attorney. I look forward to putting this experience to good use. 

Building in Public as an Acquisition Tool

Being transparent as you develop your business is a great way to build a base of loyal supporters. By discussing your challenges, you generate empathy. By sharing ordinarily confidential data, you gain trust and respect. By asking for feedback on undeveloped projects, you give people a sense of ownership of what you're building. Overall, you can obtain an audience that will route for you, and who will be more willing to buy your product or join your community.

To realize these benefits, however, your transparency efforts must be meaningful and sustained. One-off attempts generally don't cut it. Ryan Hoover (Product Hunt), Danielle Morrill (Mattermark), and Joel Gascoigne (Buffer) have all been incredibly transparent as they develop their companies. And the group deserves credit for popularizing the current build-in-public movement. Two other founders, who I would like to highlight, are the latest to join them.

  • Alex Blumberg—NPR legend Alex Blumberg is documenting his journey towards creating a podcast company via a podcast series called StartUp. Alex knows little about starting a business, so it's incredibly interesting to hear him articulate the challenges he faces. You hear him struggle while pitching investors. You hear his intimate conversations with his wife as he questions his abilities as an entrepreneur. And you hear gut wrenching negotiations over equity splits with a potential co-founder. Alex's podcasts make the empathy pour out of you, and you can't help but want to support him and his company.
  • Zack Shapiro—Zack recently sold his company Luna. Now, he's exploring new startup ideas and sharing his journey through Built in Public, a Medium collection and newsletter. While less dramatic and introspective than Alex's StartUp, Zack's writing provides an inside look at how a successful entrepreneur finds a viable startup idea that he would be happy working on. He openly discusses his influences and passions, and he provides sharp analysis of the ideas he is considering. Zack's approach is less intense than Alex's professionally produced podcast series, but you still feel as though you're apart of Zack's journey, and you can't help but root for him. 

Office Hours as an Acquisition Tool

One of my favorite ways to engage with a target audience is to host office hours. There are many use cases for them:

  • An accounting startup can offer office hours to businesses that need help with their taxes (good for customer acquisition)
  • A startup's renowned hardware team can offer mentorship sessions to local engineers that want feedback on their projects (good for recruiting)
  • A VC firm can offer feedback sessions to nascent startups (good for generating deal flow), or can offer career advice to young engineers (good for portfolio company recruiting). 

For all of these use cases, office hours offer a low-friction, low-commitment alternative to traditional interaction methods. A potential customer doesn't have to pay a hefty fee to start using a company's services. A potential investment's founder need not begin the tricky dance of attracting angel money. And a potential recruit doesn't have to formally declare that they are looking for a new job nor start the dreaded application process. They also don't have to cold-email a bunch of people or join a weekend-long hackathon just to get feedback on a project. 

It may seem that office hours don't scale well, but you would be surprised. Hired's NYC team recently hosted office hours where three of its Talent Advocates provided 15 minute career coaching sessions over a two hour period. That's 24 sessions in total, all of which were sold out. If they hosted such sessions every Friday for a month, they will have met with nearly 100 potential candidates for their startup recruiting platform. 

You may also think that you will only get low quality meetings by hosting office hours, but you would also be wrong. : ) First, not all high quality targets want to go through the high-friction, high-commitment traditional interaction methods that I listed above. And second, you can frame your office hours as a scarcity, and make getting slots a competitive process. Y Combinator recently did this by having an application process for startup feedback sessions they hosted in New York City and Waterloo. Assuming they got more applicants than slots available, they were able select who they met with. And it seems to have worked out for them.

Of course, office hours don't guarantee immediate results. But hosting them is a great way to build goodwill and to enable serendipitous outcomes. Brad Feld has been hosting office hours for over twenty years, and one of his meetings—with David Cohen—famously led to the creation of TechStars

So whether you're a startup, a VC, or simply a person capable of giving great advice, consider hosting office hours. 

What Makes a Great Newsletter?

Through running Happy Inbox, I have evaluated hundreds of newsletters. Newsletters are very much a matter of personal taste, but I have found that there are some key traits to great ones:


Capital NY's Playbook

(1) Unique Content. Unique content is paramount to having subscribers that actually read and look forward to your newsletter. Recycling content published online won't cut it. A great newsletter should also anticipate how and where it will be read, be it in bed or in the middle of the work day, and optimize for that experience. The newsletter's content should offer a striking contrast to what a reader may get from anything else at that time, and it should leave the reader with a genuine sense of feeling informed, entertained, or connected. The Mattermark Daily—which shares the most significant startup analysis published each day—stands out from competitors by providing a thoughtful impression for each article it shares. The impressions are crafted so well that you feel the gravity of each piece and you understand how they add to the conversation. Politico's Playbook (the "Godfather of newsletters," if there were ever such a thing) and Capital New York's Playbook—which feature national and New York political news, respectively—provide an "insider" take on the latest political news early each morning. The insights are so fresh and respected that, as the New York Times described, "some of America’s most influential people will read [the Playbook] before they say a word to their spouses." 


Product Hunt's Newsletter

(2) Humanized. Adding a personal, human message to a newsletter is a great way to connect with readers. Product Hunt's newsletter nails this. In each edition, Product Hunt founder Ryan Hoover adds a little message that deviates from the newsletter's primary purpose, which is to share the top products posted to the site. His messages share everything from updates on his growing company to trends that the Product Hunt team is seeing. It's this personal touch and element of surprise that I believe gets people hooked to a newsletter—even if its minor and takes seconds to consume. To the contrary, newsletters that effortlessly share an RSS feed are unlikely to have engaged readers.


Farnam Street

(3) Thoughtful Design. A newsletter's design need not be fancy or loaded with graphics to be great. The Playbook newsletters, for instance, simply contain paragraphs of text. But the basic design seems to be an almost intentional way of reinforcing that the Playbook contains pure insight—no nonsense.  A great newsletter's design is more about what it shouldn't look like. It shouldn't look automatically generated (such as from an RSS feed), and it shouldn't have lackluster graphics. But the content must be extremely readable. After that, the possibilities are endless. I love newsletters that take the effort to give you visual cues as to how to read it, such as highlighting important information or boxing special messages. The Farnam Street newsletter, for instance, literally has a heading that says "Start Here" to guide readers on where to begin reading.  



(4) Consistent Schedule. Preparing a great newsletter is not easy. It takes a lot of effort to incorporate unique content, a humanized component, and a great design into each newsletter you send. But the best newsletters meet all of these criteria while being delivered on a consistent schedule, without fail. Promising a daily newsletter yet having frequent spates of not sending it will ultimately result in reader mistrust and disengagement. You also risk missing out on the natural growth that a great and consistently delivered newsletter can experience. Dan Primack's Term Sheet and Connie Loizos's StrictlyVC excel at consistency. They rarely miss a day. But if they have to, they arrange for substitute authors—which has the added bonus of changing the rhythm and adding some excitement to an otherwise consistent newsletter experience.

For more great newsletters, check out Happy Inbox