Boutique firms are one thing; EC/VC boutiques are another. Recruiters at Whistler Partners alongside seasoned EC/VC experts give us the lowdown on these boutiques with a specialty focus.
We here at Chambers Associate have noticed that law students and junior associates often fall into a bit of a one-track mindset: BigLaw this, BigLaw that. Even if they feel like they aren’t at the right firm or in the right practice, the decision still feels stuck on two rails: keep chasing BigLaw prestige or jump in-house. But here’s the thing: what about boutiques?
Boutique firms may be smaller in headcount and practice scope, but they’re often staffed with attorneys who have the same top-tier credentials as their BigLaw peers. For those who want a different kind of experience, boutiques can open doors that BigLaw simply doesn’t. Even better, boutiques specializing in emerging companies and venture capital (EC/VC) add an extra spark, as “they almost function like a startup.” Sounds like something you can get stuck into? Here to tell us all about EC/VC, boutique firms, and EC/VC boutique firms are our friends over at Whistler Partners, as well as a whole host of EC/VC attorneys – all so you can hear it straight from the top.
Perks, Pitfalls, and Everything in Between
As with any practice, EC/VC boutiques come with their own set of pros and cons to weigh up… and who better to hear about this from than the source? Drew Macklin, founding partner of Macklin Law – a boutique firm with an EC/VC focus – details that the depth of the relationships he develops with clients makes it all worth it: “Coming at the work from a real boutique perspective allows us to fit into our clients’ structure and day-to-day as an extension of their internal team versus an external service provider; we feel like a core stakeholder in what they’re building.” A former BigLaw attorney, Macklin states that his primary motivation was to “play a material role in the new products and services that were coming into the world,” which he does now at his firm. Seconding this viewpoint is Jared Verzello, founding partner of Presidio Legal and EC/VC veteran, who highlights that “you get to work with a lot more up-and-coming people, which is very satisfying because you’re really helping to coach them and helping them understand how this very insular little world works.”
Another interviewee who made the shift to a boutique is Don Lee, a managing partner of Prospera Law’s corporate transactional group with over 20 years of experience under his belt. He finds that at a boutique, “we definitely strive to provide the highest quality work and client service, just like any other firm would, but we can do it so nimbly.” Because there is “less bureaucracy” and the absence of a “huge authority structure” at boutiques, “we can act pretty quickly,” he elaborates. With this comes the added benefit of flexibility: “You’re not just dropped into the system,” Lee explains, “We really encourage you to grow your practice how you want to grow it. If you want to focus on building clients, build your craft but go hustle those clients too; be good at what you do so you can sell it. If client development isn’t your thing and you just want to put in the hours and go home to spend time with your family, that’s totally cool too.” The pro here is that there is room for whatever “platform you need to be the best version of yourself,” he sums up. There is a plethora of other pros – including the ability to originate, skills you can gain, and lifestyle changes – but we’ll take a more in-depth look at those later.
"Boutiques aren’t for everyone... Ultimately, it's an adjustment not being at a big full-service firm."
As for drawbacks, as Nadeen Shatara, managing director at Whistler Partners, describes: “Boutiques aren’t for everyone. I know an associate who went from BigLaw to a very elite boutique, and they didn’t love that it didn’t have the same resources. For example, if they needed an employment attorney, they had to outsource the work. Ultimately, it’s an adjustment not being at a big full-service firm.” This is one of the factors that makes it difficult to compete with bigger firms, Lee admits: “You always worry about having clients poached by bigger law firms with bigger brand names, because the big firms have a deeper bench.” In the EC/VC world especially, “your practice can hinge a lot on your relationships with VCs and entrepreneurs in the community who are the referral sources,” he goes on to say, “Some VCs are tied to the big firms, and once they invest in a company, they want their portfolio to be serviced by a big firm.”
Money – which famously makes the world go round – is often another pain point for boutiques. Running a boutique means “you have to be conscious of the fact that the folks you’re doing work for don’t have unlimited budgets,” Macklin admits, “so there’s a real tension between building a relationship where they feel like they can pick up the phone and call you all the time, versus acknowledging they can’t always afford to pay for every single phone call they want to make.” The highly personal aspect of being an invaluable resource is a pro, as Verzello tells us, but “an economic relationship always underpins it” which can be difficult to navigate. So, the challenge is to “set expectations and manage the time allocation and financial pressures of a boutique-sized and boutique-focused practice,” Macklin says.
The Boutique Personality Test
Ultimately, certain people will be better suited to working in an EC/VC boutique than others. It’s a little like a puzzle: there’s no sense in trying to make a corner piece fit in the middle. Take the analogy that Sean Burke, founding partner of Whistler Partners, gives us: “I bought something to mount my phone in my car,” he starts, “I watched the installation video, and it was like: ‘You have to take a piece off the dashboard and do all this other stuff.’ It’s not that hard, but I literally looked at that video and was like, ‘I don’t want to do any of this stuff!’ So, in that regard, I am not the right person.” (Frankly, neither are we.) The right fit would be “the person who loves rolling up their sleeves and opening the dashboard themselves,” he adds.
“Because we’re a smaller shop, we’re dealing with you all the time. You have more responsibility."
Like Burke is saying, there are fundamental personality traits that lend themselves well to smaller EC/VC practices. First and foremost is being “self-motivated and a voracious learner,” Macklin affirms. Within a BigLaw firm, “it’s very easy to lean on the specialist practice groups and stay in a very narrow lane,” he explains, “All the disparate pieces that come along in a transaction can be farmed out to other people who only do that sort of thing.” Conversely, in a boutique, “it’s much harder to hide,” Lee underlines, “Because we’re a smaller shop, we’re dealing with you all the time. You have more responsibility, so it’s easier for us to pay attention to what you’re doing.” Essentially, you are a one-stop shop for a wide array of areas of law. Those who succeed are “comfortable with learning the answers to difficult questions, trusting your instincts and ability to obtain and develop knowledge, and then build on that knowledge as the transaction closes and you move on to new things,” Macklin lists. Not everyone is cut out for it, he acknowledges; it’s certainly “not for folks who want to be a mile deep and an inch wide in something,” nor is it for “those who need to learn from the top down as opposed to the bottom up,” especially as boutiques tend to staff pretty leanly. “If you’re not the right fit, we’re going to see it pretty quickly,” Lee reveals. Though if you are a good fit, “I think it’s a great place to be, because it’s all in your hands,” he adds, “If you want to bet on yourself, this is the place to do it.”
Similarly, when hiring, Verzello is keeping his eyes peeled for soft skills above all: “The reality is it’s going to be very difficult for junior associates to ever impress a senior attorney with their legal knowledge, because they have so much more experience and knowledge than you,” he states candidly. As such, in a way, your main clients as a junior are the senior people within your own organization: the senior associates and partners. Plain and simple: “They don’t really need your help with making legal judgments; they need your help with project management,” Verzello declares. Being organized with good professional communication can take you far. It may not be “the most glamorous part, but that is the actual part that inserts you into the slipstream of the most interesting deals and the best interactions.”
“They don’t really need your help with making legal judgments; they need your help with project management.”
There is, however, one specific practice area that might give you an edge if you do want to transition to an EC/VC boutique, although it’s probably not what you think. Shatara, who was a former recruiting manager for Fenwick and Gunderson, states in no uncertain terms: “M&A hands down.” Over an EC/VC attorney?! From her experience, yes, because “firms know they’d spend a bunch of time developing EC/VC attorneys only for them to go in-house after a couple of years.” Why M&A? “Those folks are really excited to be in an EC/VC practice, and to feel a more direct impact from their work,” she explains. “They’re going to stick around at that law firm longer.” M&A associates are also “more used to deal work,” Sean Mahsoul, partner at Presidio Legal, continues, “You get familiar with some of the issues EC/VC attorneys deal with on a day-to-day basis for clients because you’re diligencing those same issues in an M&A deal.”
Macklin is partial to associates from private fund formation groups because they bring with them a “real understanding of contracts.” He points out that when associates are working on those contracts in a BigLaw environment, “it’s very easy to assume that those are fund-specific pieces of paper, but the principles that underline a strong contract in those areas are actually intensely translatable.” There’s also a case for EC/VC boutiques hiring labor & employment attorneys, according to Francis Kelly, a managing director at Whistler Partners: “Startups often don’t have a robust HR department, and since they’re growing quickly, they’re dealing with a lot of employment issues. Going to an EC/VC boutique as an L&E attorney can be a great opportunity to broaden your practice and work with some really interesting clients.”
"...sometimes, you have to move to move.”
For those who aren’t in a practice that builds the skills necessary to succeed in an EC/VC boutique – such as capital markets, according to Burke and Macklin – it’s not too late… yet. For example, “if you’re at a top-tier Wall Street firm doing banking & finance, you’re an extra step removed from getting an EC/VC job,” Burke lays out, “You might have to go to another firm, switch to M&A, and then try to go into EC/VC again a year or two later.” Hard but not impossible, it indubitably “sucks sometimes,” Burke shrugs, “but sometimes, you have to move to move.”
An interesting point is made by Lee – who says he “has yet to see a practice that wouldn’t fit on our platform” – about unexpected fits, recounting the events of 2021 at Prospera Law: “We brought in a group of lawyers who had a healthcare litigation practice,” he shares, “which didn’t seem to fit with our firm on paper. Even though it had nothing to do with our existing practices, it plugged in very seamlessly. That was about common intention and personality types far more than it was about practice area.” The key is collaboration, flexibility, and the ability to be dynamic, he tells us; once you have those, it’ll be far easier to find your place at a boutique.
That's all for now, but we're back in part two to discuss origination opportunities and lifestyle changes that come with VC boutiques.
