Lawyers love certainty. Startups run on everything but. That gap is where many legal careers either stagnate or accelerate. The difference is rarely about raw talent. It is about how honestly you see the bet you are placing on your own time, judgment, and resilience.
In a recent “Notes to My (Legal) Self” episode, I spoke with Rina Wang, most recently assistant general counsel at AI startup Prepared, which was acquired by Axon. Rina has lived the full cycle many in-house counsel fantasize about: federal clerkships, litigation, multiple venture-backed startups, an AI boom role, and a fast acquisition. Underneath the glossy version of that path is a more honest reality that most lawyers never hear before they jump.
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This is an attempt to correct that.
Thinking In Bets When You Only Get One Chip
Rina said something that should be printed on every startup job description for lawyers: “I really am an investor going into this startup. I am investing my time and my career. It is human capital, but it is just as important, if not more so, than being a VC investor and throwing in money.”
VCs spread bets across 10 to 20 companies. Lawyers place one bet at a time. If a fund’s single unicorn offsets nine failures, that is a win. If your one job implodes, that is your income, your resume, and your emotional bandwidth for the year.
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During the pandemic, Rina read “Thinking in Bets” by Annie Duke and began to see career choices the way poker players see decisions made under pressure. You never have perfect information. Outcomes rarely track effort. Luck and timing shape more than we want to admit. “How do we make the best decisions in terms of uncertainty or a limited amount of data?” she asked. That is the core question of startup life.
The problem is that lawyers are trained to avoid uncertainty. We are rewarded for spotting risks, issuing careful warnings, and forecasting every scenario. In startups, that mindset is felt as a delay. The work still demands rigor, but the posture has to change from “prove this is safe” to “place a smart bet knowing it never will be.”
If you are considering a startup move, the first step is internal. You are not choosing between certainty and uncertainty. You are choosing the type of uncertainty you want and how concentrated you want your bet to be.
Graduating Into Recession, Practicing Inside Turbulence
Rina is clear that the 2008 recession shaped everything that came later. She started law school in 2007. By graduation, “no one was working. There was certainly no deal work going on.” She calls herself a “recession graduate” who learned early that macro conditions will disregard your plans.
Employment litigation during a recession gave her a flood of work and immediate responsibility. “There are a lot of juicy cases all the time,” she said. She was taking and defending depositions and drafting motions from the start. That pace and pressure later made startup life feel familiar, not destabilizing.
If you trained in environments with more insulation, be honest about that. You can build the muscles. You will feel the intensity more quickly. The key isn’t asking “am I resilient” in theory. It is asking whether you have had to own outcomes before in situations where no one could buffer the fallout for you.
Mission Is Not Fluff. It Is How You Survive the Middle.
On paper, Rina’s path looks scattered: spirits made in a lab, construction tech, and then an AI platform for 911 emergency response. The through line is mission. Environmental sustainability. Practical tools for real-world infrastructure. Public safety.
She also chose male-dominated industries. “I had this urge, and this need to kick down doors for myself and create a seat for myself at the table in these spaces where there was not a lot of diversity.” That choice made her path harder and sharper by design.
Mission is not a soft factor for lawyers in startups. It is what carries you through the middle chapters: a tough funding round, a volatile market, a surprise product shift, or in Prepared’s case, an acquisition process triggered in part by the CEO being hospitalized with a spider bite that nearly cost him his leg.
This is the deeper point behind thinking in bets. You cannot predict the details. You can only decide whether the mission, team, and customers matter enough that the volatility is acceptable.
If you are evaluating a startup, ask yourself plainly: Do I want to think about this problem for three to five years? Do I respect the customer? Do I believe the world is better if this product scales? If the answer is lukewarm, the bet is mispriced before it even starts.
The Emotional Reality Of Being ‘Calm’ During An Acquisition
Prepared announced its acquisition by Axon on September 23, and the acquisition closed on October 1. Internally, the intensity had been building for months. None of that shows up in the press release.
Rina described the internal experience this way: “Everybody expects legal to be calm in the eyes of the storm.” You become the anchor for a team that may be anxious, disoriented, and overwhelmed by the unknowns. That expectation comes at the exact moment your own role may be at risk.
She added, “I am more than comfortable admitting, hey, this is a new situation for all of us. We are building the plane as we are flying it.” The company did not know an acquisition was coming months in advance. Conversations with Axon moved quickly. Internal reorganizations were happening in real time.
Staying functional required honesty instead of forced certainty. The leadership team respected that more than pretense.
If your company is heading toward an acquisition or operating in a consolidating market, prepare yourself emotionally as well as legally. You need peers who can normalize what you are going through, mentors who have lived M&A integrations, and enough personal structure to process the experience without letting it consume you.
From Risk Avoidance To Value Creation
This is the pivot that matters most. In a firm or a large company, you can succeed by being a highly accurate legal technician. In a startup, that is not enough.
“If you are just pointing out the law and regulations, you are not adding any value separate and apart from outside counsel,” Rina said. Startups need generalists who can negotiate commercial deals, structure partnerships, build privacy and security foundations, and support product decisions.
Your value shifts from risk minimization to enabling the company to move. You are no longer a step in a workflow. You are part of the engine.
Before joining a startup, ask yourself: Do I enjoy working directly with sales, product, and engineering teams? Do I know how to connect legal risk to revenue and growth? Can I move at a speed that sometimes feels uncomfortable? These are learned skills, but only if you want to learn them.
Seeing Your Career As A Series Of Intentional Experiments
At the end of our conversation, I asked Rina for a final takeaway. She said, “Be humble to uncertainties. A lot is not within your control. A lot is luck and timing.”
That humility is not resignation. It is clarity. If you understand that you are making a bet every time you choose a job, you can make better and more intentional choices. You can evaluate missions more honestly. You can prepare for volatility instead of resisting it. You can show up as a legal operator who helps the company move, not one who braces against every risk.
Startups are not for everyone. They are also not inherently reckless or chaotic. They are experiments in speed, mission, market timing, and people. If you choose well and place your bet consciously, one intense year can stretch your career further than 10 quiet years anywhere else.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty. A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics. She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.