Interview With Bradley Tusk, Managing Partner, Tusk Ventures

Bio

Bradley Tusk is the founder and CEO of Tusk Ventures and Tusk Strategies. In politics, Bradley ran Mike Bloomberg’s successful 2009 mayoral campaign, served as deputy governor of Illinois, and as communications director for U.S. senator Charles Schumer. In business, he has worked with dozens of Fortune 500 companies, institutions, and startups to help them tackle regulatory hurdles, including AT&T, Google, Stanford University, Uber, Handy, and FanDuel.

Tusk Ventures is the first political strategy firm focused on helping startups navigate the political, regulatory, and media hurdles that come with reshaping entrenched industries. Bradley is also the founder and funder of Tusk/Montgomery Philantrophies, which focuses on fighting hunger through new legislation and new technologies.

Bradley is also the author of The Fixer, where he deploys the skills and knowledge he developed working with Chuck Schumer, Michael Bloomberg, Rod Blagojevich, and other political and business legends to help startups fight back. The book goes behind the scenes on how he helped stop the taxi industry from killing Uber in its infancy, how he held insurance companies at bay while startup Lemonade launched in each state, and how he helped online sports betting sites FanDuel and Draft Kings escape the regulatory death grip casinos tried to put on them.

Interview

In the middle of fierce competition for hot deals on the VC side, many VC firms use unique positioning by providing services and exploring unique angles. How does this unique angle help you stand out from other VC firms? Any tips for up-and-coming partners of new firms?

For us, differentiation is everything. The reason why a company either makes room for us in a round, expands the round to include us, or chooses us to lead the round is because they know they’re going to face real regulatory headwinds and they want us as invested and incentivized as possible to solve them.

In terms of deal flow and winning deals, having a truly different skill set and value add is tremendously helpful. However, it hasn’t been that helpful so far for us in raising funds (we’ve gotten there but LPs still are generally more comfortable with the traditional resume and approach).

Portfolio ventures that are going great need almost no support, and the ones that are in the bottom aren’t worth helping. Apart from the two extremes, how do you know how much effort, time, persistent to put in the ones that are somewhere in the middle? How important is the regulatory/political context of the startup for this triage?

This is one of the hardest questions we face every day. Because of the nature of our work, our portfolio companies often need our support even when things are going great (they still have regulatory, political and media issues to deal with) so we don’t face the same cycles as everyone else. But generally speaking, knowing how to think about and deal with companies whose fate is very unclear is a constant challenge.

How do you balance your time between (1) sourcing quality prospect ventures (2) doing due diligence for prospective investments and (3) helping current entrepreneurs? Which of these are you comfortable outsourcing to principals/analysts and which do you absolutely have to do yourself?

Both Jordan and I and the others on the investment team do all three. Most of the high level opportunities tend to come to (or are found by) Jordan or me, but one of our younger team members found and brought in Roman, which is one of the best companies in our portfolio.

Diligence for me and Jordan is more around asking hard questions and playing devil’s advocate than doing research and building models. And in our case, helping our portfolio companies comes from the investment team but also the regulatory, political and communications teams here too. It’s possible for a dozen people here to work with a portfolio company in one form or another.

Many GPs are good investors but don’t master one of the core skills — adding value as a board member. What do you think are some tricks to a productive relationship with founders? What should the culture be for the board and CEO for a quality relationship?

For us, we really try to focus on and add value around our core skill set both because founders want and need it and it’s something we know really well. That can happen as a board member (we have seats currently on four boards) but doesn’t necessarily need to — we just need to be able to offer our expertise and ideas and make sure they’re taken seriously. Obviously, transparency and honesty is the key to a healthy relationship between the board and the CEO.

How do you solve important conflicts with CEOs, such as lack of alignment on exits, strategy, or even emotional issues such as the CEO being in denial about things like performance? Does the resolution begin with a private conversation or escalating and involving other board members?

It usually starts as a point of concern within our own investment team, then grows enough to merit a conversation with the CEO, and if that doesn’t bear fruit (after multiple attempts), then it could spread to other board members and investors. But if you’re immediately going around the CEO, that’s a sign of much larger problems.

When raising money from LPs, what is the thing you emphasize the most when “selling” the fund? Past returns? Team expertise (domain and/or entrepreneurial expertise)? Your unique angle?

For us, it’s our unique skill set and value add to startups. The fact that Fund I has a net IRR of 65% certainly doesn’t hurt either but because we’re still pretty new, we haven’t had any official exits yet.

LPs never really question our competence around politics. They want to know that we have all of the other tools necessary to run a successful fund. That’s why Jordan and the team are so critical and it’s why talking to the founders in our portfolio, other VCs we partner with, and our current LPs can mean so much.

Key Lessons from Bradley

• A unique angle is good for winning dealflow, but not that helpful for raising LP money from conservative allocators. While nascent entrepreneurs recognize a unique value add from a VC investor easily, prospective LPs might be used to a specific cookie-cutter model;
• Value add as a GP can happen outside or inside the boardroom. While adding value as a board member is important and should be mastered by the GP, as long as you can add value and propose valuable ideas, this communication can occur outside a board member role;
• In a new fund with no exits yet, master all the other tools. Unquestionable expertise in your field, relationships with key founders, key co-investing VCs and key LPs are crucial apart from returns;