- Exec at multiple, medium sized companies - Early employee at two companies that reached >$1B exits - Bay area local Ask me about: - How to be successful in product management - How to rise the ranks in PM - How to navigate start-ups & equity
How did you decide to join the two startups at such an early stage?
The first one, I didn't really have many options and was early in my career. So lucky that one did well. The second was easy because I caught the startup bug and wanted more.
This is a bad answer that helps no one.
What are some of the risks that you had to take to join a startup? Why did you make this decision?
The risks were a bit different back in the day. I joined a startup during college, but felt like I didn't know what I was doing. After college, I joined a mid-sized company for 3 years and then went back to startups. This was about a decade ago, so I didn't have to forgo the big RSU packages that you see nowadays. The main risk that is true back then and today is that if your startup doesn't go anywhere -- it's a bit harder to get your next job and continue the momentum.
Is it worth keeping working for others when you have a sufficient financial moat of your own?
Good question. It's hard to start something from scratch and the early years are grueling. Whereas, you can plug into a larger company and focus on higher order problems. The sufficient financial moat allows you to play offense versus play your career defensively.
Completely agree with this as someone who has had 2 successful exits myself (1 ipo and 1 big acquisition). Every now and then I get the startup itch again but then I remember how grueling the early years are
With a 1B+ exit, how much did you make as a pm exec and how much did you make as a startup employee?
Nowadays, people are doubling and tripling their salary with stacking RSUs. At a startup, you get a modest salary and equity. Since the average time to exit is 7-10 years, you're potentially missing out on a lot of real cash. For the startup to make sense, you need to be making millions upon exit.
You didn’t answer his question
What does good product management look like for you? There are enough books that discuss utopia, and enough that talk about nightmares. But rarely do people discuss the challenges and the balancing act that is product management.
Tough question to answer. It depends on the kind of product, company, and level of maturity. Because the job is so vast and you have to be good at so many things, I see it as a master/apprentice model. I've probably had 4-5 key individuals in my career who really helped me grow quickly.
TC or GTFO
Made millions from startups and cruising now >$500K
How did you negotiate equity at these startups? Given your experience, what would you recommend people do?
If you're an incoming exec, it's easier to negotiate equity as you join. If you're an unknown quantity, the best strategy is to kick ass in Year One and then ask for a bunch.
I am kinda in that position now, I work for a startup with a serial entrepreneur and her only PM on a 5 person team. I joined with no equity because the company was just an idea being incubated at a studio and now we're on the verge of setting up our own company and they're thinking of giving us convertible notes. I would like to position myself as CPO of this little startup (I know I have kicked ass bringing us from zero to one) in time but I'm curious how you think I should negotiate? 2nd related question, any experience with neogotiating in the context of convertible notes? Thank you for doing this! I'm sorry some of the other comments have been, well, harsh 😔
What do you look for when hiring pm’s? (Skills+background+prior companies)
Depends on the role. One helpful framework is that there are generalist and domain experts. I can put a generalist on any tough problem, and the domain experts are necessary to make fast traction in a complex area (e.g. SEO, search, ML, etc). It's hard to find great generalists. These people have a track record of pulling rabbits out of a hat and delivering unexpected results. Their stories should impress you.
I like this response, but having recruited for PM roles in the Bay it seems the reality is the exact opposite. Everyone wants x years as a PM drone at Amazon, not stories.
What kind of a background did you have? SWE/MBA/Other type of engineering?
EECS from UC Berkeley. Considered MBA, but never got around to it.
Nice! What class gave you the most trouble/hardest in undergrad for EE/CS?
When you started investing actively (personally). Did you lose money?
Barely started investing since some of the exits happened just a few years ago. Taking a pretty conservative approach right now, bogleheads.
Can you give a breakdown on where do you invest your money ?