Josh is a Partner and Chair of Northern California at DLA Piper, where he advises life sciences, healthcare, and technology companies across the full company life cycle, from formation through private financing, M&A transactions, and IPOs. Previously, Josh served as the global chair of Cooley’s Digital Health Group and the firm’s Life Sciences Advisory Board, handling over 300 venture capital financings since 2020. Josh brings deep industry insight from his background in digital healthcare, regularly guiding clients on corporate governance, securities, as well as complex business transactions.
How do you bring ideas to life?
Generally, I try to be thoughtful and get all the inputs I can. In the venture capital and legal space, the focus is typically trying to solve a client’s problem. Sometimes they come to me with a specific outcome they’ve already predetermined, but in many cases, the solution they are thinking of is too heavy-handed.
Once you understand the underlying objective first, there are a multitude of solutions, some of which don’t need as much leverage because the subtle solution achieves the same objective. In my business, almost everything I do has to work from a tax perspective. One of my mentors told me that a good corporate lawyer has to have a great tax lawyer as a partner, or deals don’t get done properly. I’ve always taken that advice to heart.
What is one habit that helps you be productive?
For me, it’s trying to keep sight of what I’m doing these things for. I always like to tie the current task back to something concrete in the real world, like helping a company hit a major milestone or seeing the tangible impact of a successful deal. Having that kind of personal connection to the outcome lets you power through those late nights when the work feels all-encompassing. It gives you a ‘North Star,’ and I find that to be very calming.
Tell us something you believe almost nobody agrees with you.
I think sometimes people are looking for the quickest way to get done with something, and I typically find that’s not the right way. Even if it means some additional sacrifice, I still drive hard for the right answer. It’s becoming a “rare bird” that is willing to push past midnight to finish the last piece of a project versus trying to get some rest a little earlier. I’ve always believed that the willingness to go that extra mile is what separates top-tier advisors who achieve outsized results from the rest of the field.
What is the one thing you repeatedly do and recommend everyone else do?
Make sure that you’re listening to your own internal voice. You have to learn to trust your decision-making ability. You can analyze things five ways to Sunday, and it’s easier than ever to analyze facts with AI tools, but the one hard thing to conceptualize is your internal reaction, your gut.
Having a strong instinct makes a big difference in your ability to make decisions. You shouldn’t dismiss that feeling because you have to live with your decisions and go to sleep knowing you made the right one. If you can’t align the facts with your gut, something’s off. You have to develop judgment because that’s ultimately what people hire you for.
When you feel overwhelmed or unfocused, what do you do?
When I get to that point, I like to take a pause, step out, and just try to regroup. A lot of times, that’s when I might feel I’m not performing at my best. I’ll just step away and then try to get up early the next day and tackle the problem again. Sometimes, when you separate from something and give your brain a chance to clear, you can see the problem from a different angle and come up with a good solution.
What is one strategy that has helped you grow your business or advance in your career?
My strategy is to put the client first at all times. I make sure to solve their problems in a manner that makes their life easier. It could be just small things, but, at the end of the day, they all add up. If I can spell something out in an email so they don’t have to open up a document, that is one less thing they have to do.
When you do that on an aggregate basis, it results in a better overall experience. People appreciate it when you’re trying to think about the world through their lens.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
When I was much younger, I didn’t make the varsity basketball team I had my heart set on. Instead, I was placed on the junior varsity squad. It was a massive wake-up call because I realized I hadn’t done everything in my power, specifically in terms of my work ethic and preparation, to earn that spot.
It taught me that if you want to achieve a specific objective, you have to invest the time to develop yourself before the opportunity arrives so that you’re actually ready to grab it. I’ve never looked back on that lesson.
What is one business idea you’re willing to give away to our readers?
Don’t take the status quo for granted as though it’s a mandate; you can achieve outsized results simply by doing things differently. In my world of representing founders and startups, people think forming a company is a cookie-cutter administrative exercise.
However, there is a massive advantage in being more thoughtful about the structural details, such as founder tax planning during the initial formation, specifically regarding Qualified Small Business Stock (QSBS).
For instance, issuing stock to a trust instead of directly to a founder can result in $15 million or more in tax-free gains when the securities are eventually sold. Most people miss this because the process seems mundane, but digging deeper into the strategy at the very beginning makes a life-changing difference.
What is one piece of software that helps you be productive? How do you use it?
I use a lot of tools like task managers and project management software to ensure compliance among my team, and I’ve been using more legal AI recently. But the tool I use the most is a printer. I really enjoy reviewing something when I can hold the piece of paper in my hands. It’s not consistent with how the younger generation practices law anymore, but I find it to be the most helpful for issue-spotting and general quality control.
What is the best $100 you recently spent?
That’s a pretty easy one for me. I recently participated in my daughter’s school auction, which they have every year, and I bought the “Principal of the Day” experience for my soon-to-be second grader.
To me, that’s by far the best thing I’ve bought recently. In life, if I can help create a memory that I can actually be a part of, that is just very, very rewarding. It wasn’t just about the purchase; it was about the experience for her and the fact that it goes to a good cause for the school. Being able to create those kinds of family moments is a huge priority for me, and this one was really special.
What’s a movie or series you recently enjoyed and why?
I’ve actually been going backwards in life lately and watching Harry Potter. It’s not necessarily something I would have chosen to go back and watch on my own, but it’s been a really fun experience because of my oldest daughter.
She just finished reading the first book, and we’ve made a deal that every time she finishes one of the books, we sit down and watch the movie together. It’s been a lot of fun to experience it through her eyes as she sees the stories she just read come to life. Even if I wouldn’t have sought them out otherwise, it creates a really good family moment for us.
Key learnings:
- Connect your tasks to something concrete in the real world. When action meets personal connection, success becomes more tangible.
- Decision-making backed by strong instinct makes a good leader. People hire you for your sound judgment, so focus on developing that.
- Prepare for opportunities and be ready to achieve your goal when the time comes. Achieving outsized success comes from doing things differently.