Experts at Whistler Partners and seasoned industry professionals give us a peek into life at an EC/VC boutique in the second part of this two-part series.
We're back and ready to get into more on EC/VC boutiques with Whistler Partners. If you missed it, don't fret. Read part one here, where we discussed the pros and cons of working at a boutique, as well as the personality traits and practice areas that lend themselves well to VC boutiques. Now, let's get straight into it.
From Associate to Trusted Advisor
The realities of working at an EC/VC boutique include access to opportunities that allow you to develop skills you wouldn’t otherwise be able to build. Associates in BigLaw are “generally not even dealing with the person who has the authority to say yes or no,” Don Lee, a managing partner of Prospera Law's corporate transactional group, notes, but in an EC/VC boutique, “the advice you give makes a big difference, and the person that you’re talking to usually has the authority to say up or down.” So, associates must learn how to “structure their advice in a very practical, business-oriented way,” because “when you build that relationship with the entrepreneur, then it’s a foundational relationship; you are the consiglieri, and your advice is really going to the heart of how this business is going to work.” This is especially true of early-stage startups, says Francis Kelly, a managing director at Whistler Partners, and adaptability is a key area of growth here. “If your client is early-stage, you’re probably working directly with the founder in some capacity.” Whistler's founding partner Sean Burke seconds this, emphasizing that “you really are their go-to person. You’re having to field fast-paced questions that are more business-oriented than they are legal, and you really have to be flexible and adaptable.”
A huge selling point for boutiques is the ability to take ownership over generating business and bringing in clients – also known as originating. “Lower rates make you a lot more approachable,” Sean Mahsoul, partner at Presidio Legal, begins, especially for the types of clients EC/VC attorneys tend to serve. “Our model makes top-tier EC/VC counsel accessible to early-stage founders who are mindful of their budgets,” he continues, “That accessibility builds trust early and opens doors for long-term relationships — it’s a great environment for partners to originate and grow with their clients.” The business model of a boutique firm “usually allows boutiques to pay partners higher percentages on their originations,” Burke nods. They can afford to do this because “they don’t have that same real estate footprint, or all of the associates” that BigLaw firms do. Burke continues: “They really are a lot more lean and mean, and clients are coming to them because partners do a lot of their own work, rather than a team of associates being managed by a partner.”
“That accessibility builds trust early and opens doors for long-term relationships — it’s a great environment for partners to originate and grow with their clients.”
There’s also a marked difference between what you’re selling in a BigLaw firm versus a boutique. As a BigLaw associate, the pitch is: “We’re the unimpeachable brand-known experts. You cannot go wrong with us,” Presidio Legal's founding partner Jared Verzello lays out, “It’s all in-house. We have all the deals, all the market intelligence, and all the data.” The other side of that coin is that “you’re premium priced,” he caveats, “so it’s not uncommon for fourth or fifth years – who’re just getting to the point where they want to start dabbling with business development – to try to land clients, but their rate might be $1,200 an hour.” It’s harder for associates to throw their name in the ring in these situations, because “anybody who can afford $1,200 an hour has probably been in the ecosystem for a while and knows people more senior than you who they would go to as their originating source.” On the boutique side of things, attorneys “find little niches,” as Verzello puts it; thus, “the value proposition is entirely different,” he states, “You’re also experts, but you’re very niche and focused. You don’t do everything, but you do it at a more affordable price. That’s your competitive advantage.” Regardless of the environment, the non-negotiable that allows you to successfully originate is to be a subject matter expert in your practice, Verzello claims. “If you spent the last four years doing middle market M&A deals and you’re now trying to do business development in EC/VC,” he laughs, “somebody’s going to eat your lunch because you just cannot credibly say that you’re an expert! It doesn’t matter if you’re billing $300 or $2,000 an hour; people only want to hire lawyers that are the best at what they’re doing.”
It is a common phenomenon for self-starters who are chomping at the bit to originate to feel stuck in BigLaw where “it’s hard to make an impact, get your own clients, and to get credit even if you manage to do it,” Burke nods. “When I was an associate, the idea that I’d have to wait 10 years before I could even scratch the surface of having my own clients and originating?” he recalls, “For me, that was super demoralizing.” It’s not the firms’ fault, he notes; “that’s just the BigLaw business model,” shrugs Burke, “A fifth year who could in time become a partner who originates versus a fifth year who is a great attorney, but may never originate? Those associates are treated the same at a big firm.” At boutiques, “they prefer the associate who will originate, and they encourage you to try,” Burke compares. “When you originate work at these boutiques, they support you, but it really is you doing it. You take the meeting, the client gives you the work, and you do the work. It’s a faster track to having clients that are yours and to getting origination credit.” Lee corroborates Burke’s viewpoint, adding: “People are coming out of big firms who’ve come up with a few $100,000 worth of business, but in a $100 million to a billion-dollar revenue law firm, that just doesn’t move the needle.” He speaks about his role in lending associates a helping hand with origination. “If an associate needs help pitching a client, I’m happy to join them on a pitch, and I’m not going to sit there and claim the origination credit for it,” Lee tells us, “It’s their client! I’m happy to help, and it’s good for the firm. We all benefit. So, I want you to bring in the client, but once you bring the client in, I also want to make sure you do good work to keep them happy.”
“People are coming out of big firms who’ve come up with a few $100,000 worth of business, but in a $100 million to a billion-dollar revenue law firm, that just doesn’t move the needle.”
Ultimately, a lot of origination is about who you know, and “referrals often come from people who’ve seen you take the leap to build something of your own,” Mahsoul explains, “That entrepreneurial mindset resonates with founders – they recognize the same drive and are eager to work with someone who’s walked a similar path.” Relationship building is huge, Nadeen Shatara, a managing director at Whistler, agrees, so “if you make a connection early in your career and they go in-house and you go to a boutique firm with lower rates, it’s a win. They want to have trust in their outside counsel, even if they’re at a early-stage company where BigLaw rates are cost prohibitive.” Trust is key in the eyes of Drew Macklin, founding partner of Macklin Law, too; he adds that “once you become a trusted advisor,” to one client, “you become the person who’s top of mind when one of their friends or colleagues is starting a venture or asks around for a good lawyer. That’s the best way to build a book of business.”
Life Beyond the Billables
If you’re unhappy at BigLaw, don’t mistake moving to a boutique for a panacea to all your problems. In other words, you can’t just slap a boutique band-aid on your dissatisfaction and call it a day! Your lifestyle may be subject to change upon making that move, and boutiques tend to attract a certain type of person anyway. Take it from Macklin: “We tend to work with folks who want to have their own evenings and weekends with their family to begin with. So, they don’t have the same kinds of expectations of 24-hour, around-the-clock service that a larger, multinational company might have.” The hours are a big driver for people looking to leave BigLaw, but “it’s all relative,” Shatara informs us. “Some associates aren’t bothered by billing 2200 hours, while others are crushed at 1800. Some boutiques will be fewer hours than your current BigLaw job, and others won’t. It’s all about aligning expectations.”
“I’ve tried to cultivate an atmosphere and culture where the job supports our real life as opposed to the other way around.”
The other huge thing – the “elephant in the room,” as Kelly calls it – is money: “Sometimes you have to take a pay cut when you go to a boutique,” he admits, “whether it be because they’re letting you retool, or because they are charging their startup clients lower rates – there’s usually a bit of a comp hit from the BigLaw salary.” So, Macklin advises, “to the extent you’re someone who’s just focused on your bottom line, a boutique is probably not going to be the place for you.” This trade-off may be worth it if you’re looking for a more “sustainable” lifestyle, Verzello laughs: “You can actually, like, have relationships, have a family, see your dog! You know what I mean?” The culture is also different: “At my firm, there’s a lot more flexibility in terms of PTO, and it’s a little less rigid in terms of accruing time off and being able to step away for an appointment, a dinner, or whatever it may be,” Macklin shares, “I’ve tried to cultivate an atmosphere and culture where the job supports our real life as opposed to the other way around.”
But this doesn’t mean moving to a boutique is a free pass to rest on your laurels, Lee says: “I strongly disagree with the perception that going to a boutique firm is a lifestyle move, and we do hear that notion from BigLaw associates who are interested in us.” Attorneys at boutiques still “work weekends, we work nights, and we do whatever it takes to get the deal done for our clients,” he nods, “We work very hard.” Indeed, and Mahsoul co-signs boutique firms as a solid BigLaw alternative, even for those looking to off-ramp: “If you don’t get your BigLaw dream job right out of law school, a boutique is a great option to get real deal experience,” he affirms, “If your goal is to end up at a large law firm or tech company, boutiques can be a really good pathway to that.”
Red Tape, Relationships, and Real Access
“One of the benefits of working with us is there’s a better chance than not – especially within the tech and EC/VC space – that we know the partners the candidate is meeting with,” Kelly details. Seriously – “if we have a great candidate, 99% of the time we can shoot an email directly to the partner at the boutique who we have a relationship with,” he continues, whereas at a BigLaw firm, there are a few more “hoops and hurdles just from an administrative angle on the procurement side.” In BigLaw, recruiters have to submit through the firm’s portal regardless of existing professional relationships with the partners. “There’s usually less red tape to the boutique processes,” Shatara corroborates, “which is nice because a lot of partners are very open to building relationships with recruiters who can find them solid candidates.” Boutique firms tend to limit the recruiters they work with to a handful of trusted confidantes: “They don’t want 50 resumes; they want three,” Burke explains, “and they want to know if you really are interested in their firm.”
“We have an impressive bench of partners we work with – especially in this tech, venture, startup space..."
Burke takes an incredibly optimistic view to the challenges of legal recruiting: “Thank God for the red tape,” he laughs, “We’re not recruiters; we’re red tape experts.” What makes recruitment even more intense to navigate is the number of hats recruiters have to wear. “We are not just legal recruiters,” Shatara confirms, “we are cheerleaders and hype men. I have hour-and-a-half calls with candidates that just need to vent through whatever is going on in their life. It might be an interview, or it might be family stuff. Maybe they just need to think out loud.” Whatever the case may be, “we’re a resource for them. Having those relationships with boutique firms gives us more access and opportunities for candidates,” Shatara notes. “We have an impressive bench of partners we work with – especially in this tech, venture, startup space – so we’re very well positioned to find you the right firm, even if you haven’t heard of that firm yet,” Kelly underlines.
