PM exec and early startup employee ($3B in exits) - AMA

Nov 3 337 Comments

- 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

comments

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TOP 337 Comments
  • Facebook jdhdbhw82
    How did you decide to join the two startups at such an early stage?
    Nov 3 16
    • SAP olva73
      Control your losses too... don’t go all equity unless you have other income. Don’t go all cash compensation either unless you’re literally living hand to mouth... find a blend on the salary and startup stock.
      Nov 3
    • Facebook maple dip
      It was a good answer, he basically said it was just luck because that's what it was. Do you want him to make up some get rich quick scheme and sell books on it?
      Nov 3
    • Travelport / Eng buttnpushr
      Higher risk, higher reward and then luck. Sure you can pull multibillions out of two startups but you can also, much more likely, end up with the added stress and lower compensation for nothing to show for. There is nothing "deterministic" about it
      Nov 3
    • Google NwUp51
      You said much more likely so that means you answered what is deterministic ;-)
      Nov 4
    • Travelport / Eng buttnpushr
      Well yeah, deterministically startups pay less
      Nov 4
  • New
    With a 1B+ exit, how much did you make as a pm exec and how much did you make as a startup employee?
    Nov 3 20
    • Daimler bibimbapy
      @harre no, liquidation preference just says that holders of preferred shares (mostly VCs) get their money back before any distribution happens AFAIK. Their shares are still part of the total number of outstanding shares.
      Nov 3
    • New yMiP15
      1% for key employees at exit is a lot. How much did you get for each of the startup at the early stage?
      Nov 3
    • Google xrfn74
      OP — Which bucket were you in, and how much did dilution and preferences affect your outcome?
      Nov 7
    • OP
      I believe preference only kicks in when the exit is lower than prior valuations. From that respect I was fine. But every round raised does dilute people by however % is purchased by the investor. It’s nice when startups gives refreshers. I received auto 50% refreshers to help counter dilution for each grant that staggers down.
      Nov 7
    • Google xrfn74
      Makes sense. How long did you stay? If you leave early (after 2-4 years) should you worry about dilution?
      Nov 9
  • Northrop Grumman / Eng Lambda2
    When you started investing actively (personally). Did you lose money?
    Nov 3 18
    • Dell LUHV04
      So there is a entity called as total market stocks where you can put your money ?
      Nov 5
    • OP
      SCHB for example
      Nov 5
    • Airbnb Faridabad
      SCHB only is not Bogleheads. You’re not holding international stocks.
      Nov 5
    • OP
      I did have int’l at one point and sold it to buy property. You don’t have to follow things to a T.
      Nov 6
    • Airbnb Faridabad
      Not having itl is not just a minor adjustment. It’s core of the Bogleheads strategy. You are timing the market and betting on the USA only.
      Nov 6
  • Salesforce kuttekidum
    Is it worth keeping working for others when you have a sufficient financial moat of your own?
    Nov 3 5
    • OP
      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.
      Nov 3
    • Facebook rlBt61
      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
      Nov 3
    • Google NxNd38
      Can you be specific about what makes early years grueling? Where and what makes the transition of a startup that is more steady? (Vc invest or traction, etc)
      Nov 3
    • OP
      Good to hear @rlBt6. I was never a founder or cofounder, but it's commonly talked about in all kind of articles and podcasts. Starting something from scratch is all-encompassing. You start with an idea and maybe get a few people on board. Your resources are limited so you can only build so much. You probably need to raise money along the way and need to over-sell what you're doing. You probably need to make some pivots or major course corrections as you go. People will come and go -- especially ones who are extremely like-able and culture-building. It's the opposite of stable.
      Nov 3
    • Facebook 1111000111
      Starting a company from scratch is hard and grueling because there’s no infrastructure unless you build it. Lots of mundane details like how to create purchase orders. What levels of approval should people have. Etc... it’s a huge task
      Nov 4
  • With your current net worth and income, what does the road to retirement look like for you?
    Nov 3 6
    • Amazon / Eng OlAl28
      3 mill isn't enough to retire? JFC
      Nov 3
    • Amazon USSW74
      3 million is not enough to retire with a 'tech exec' standard of living in California.
      Nov 3
    • Tableau / Eng
      WorkingIt

      Tableau Eng

      PRE
      Microsoft
      WorkingItmore
      It’s a bit silly to attempt to retire in the Bay Area now-a-days. What’s the point? If you stay to be close to friends, you will discover most will move away anyway. If you stay for the culture, you will discover when you have a lot of time on your hands, the Bay Area isn’t nearly as good as many other cheaper and much more beautiful locations. If you stay to be able to brag and show off your wealth, you have totally missed the point.
      Nov 3
    • Amazon / Eng OlAl28
      I'm in Seattle and even I'm planning on leaving ASAP. These tech hubs are good for career growth and TC, but not retirement imo. Elsewhere he said he grew up here though, and I didn't grow up in Seattle, so that may explain it
      Nov 3
    • OP
      True that @workingit. Exploring other areas.
      Nov 3
  • Amazon soulsurfer
    How do you do your due diligence as a potential employee for a startup. Given, investors and all are well adept at it and have the tools and means to do it. But potential employee could fall into obvious traps.
    Nov 3 4
    • OP
      Yea it's tough. If you're a beginner to this stuff, you have to go with your gut. If you're a bit more advanced, you might be able to identify a few things that stop you in your tracks.

      Almost everything is just a thesis at this stage. I would ask questions like:
      - How much money is in the bank and when do we run out?
      - What's our next milestone that our investors need us to hit?
      - What do you need from me?
      Nov 3
    • Google prodpeep
      And ask the extra questions necessary to understand how much your equity could be worth. Startups pretty much never share how many share outstanding there are until you pressure them -- 100,000 options may sound like a lot until you find out that there are 500M shares outstanding, so think in percentages and what that might end up at after additional funding rounds. Also, make sure you understand the capitalization structure if you can -- what are the preferences like for the institutional investors? It may require a liquidity event of $500M before employees make a penny on the equity.
      Nov 3
    • OP
      Agreed on shares outstanding. The cap tables aren't readily shared though. One of my fav things to do when a company goes public is to look at their S-1 and see what % the top shareholders have. Check Edgar SEC.gov
      Nov 3
    • Google prodpeep
      I've found the start-up CEOs will often share where the preferences are at with the existing investors, once I've passed all of the interview stages and have an offer in hand. Definitely not guaranteed but important to understand if you can.
      Nov 3
  • What do you look for when hiring pm’s? (Skills+background+prior companies)
    Nov 3 3
    • OP
      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.
      Nov 3
    • New FRut71
      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.
      Nov 3
    • OP
      Yea maybe if they're just looking for a doer.
      Nov 3
  • Amazon / Product
    T2

    Amazon Product

    PRE
    TripAdvisor
    T2more
    Could you give insights on how to rise ranks as a PM. What are things to do and not to do? Thanks in advance.
    Nov 3 4
    • OP
      In the early levels, prove that you're the best at shipping. In the middle levels, show that you can deliver unexpected results. In the higher levels, show that you can lead -- that people want to work for you, not feel like they have to work for you. For all levels, show that you are more strategic. That you're able to identify the choices in the moment, justify the best one with some kind of evidence, and get buy-in. This can be around what features to prioritize next, or what initiatives to work on next, or what areas to invest in as a business.
      Nov 3
    • Amazon / Product
      T2

      Amazon Product

      PRE
      TripAdvisor
      T2more
      Could you clarify what you mean by unexpected results. Some examples would be great.
      Nov 3
    • OP
      Yea good question. Most companies do goal-setting or OKRs. I'm talking about exceeding those expectations. Blowing the goals out of the water.
      Nov 3
    • Microsoft ErranMorad
      What does “best in shipping” mean for a PM? Isn’t a PM at the engineering team’s hands to deliver?
      Nov 5
  • Google prodpeep
    Fun, your journey sounds a little bit like mine. Worked at four startups, three were acquired or went IPO, two went bankrupt, average TC around $400-500K per year when factoring in the random equity payouts along the way. Now at Google making about the same in TC with much more consistency and less stress...
    Nov 3 4
    • OP
      Nice! What was it like when the startups went bankrupt? And now what is your outlook on your Google job?
      Nov 3
    • Google prodpeep
      Of course it's stressful when start-ups don't succeed, especially when you've helped build the team and you still believe in the product and opportunity. Good PMs are generally optimists so that makes it especially difficult during a bad spell, because the next funding round is "just around the corner" but you're having to lay people off and still project a positive image for those who remain. But of course it's also thrilling to experience growing from a handful of people to hundreds/thousands and seeing a start-up though to acquisition or IPO. I'll probably be a start-up person again some day. For now, I'm very happy at Google. Working on a great set of technologies surrounded by smart colleagues and the role has a lot of impact...
      Nov 3
    • OP
      Very nice. And probably making connections that could help you in your next venture. Thx for chiming in!
      Nov 3
    • Splunk 9dheu3
      Yeah this is why joining a startup can be pointless. It's great early career when you dont have the clout to be at google yet though.
      Nov 3
  • Amazon vr38dett
    Survivorship Bias. For every one of them, there are hundreds, if not thousands, equally capable that did not make it my by not being at the right place at the right time.
    Nov 3 6
    • Twitch / Product thisisfun
      Lol. There are also only something like 32 teams in sports. The fact that you believe going viral on platform whose algorithms are black box and constantly changing is attributed to skill more than luck... 😏
      Nov 3
    • OP
      Well it happened. It required high attention to detail and discovering undocumented API calls. What you're saying is when you're one of the companies who didn't go viral and making excuses.
      Nov 3
    • Twitch / Product thisisfun
      Sure 😉
      Nov 3
    • Oracle LAoh31
      Come on. This is human nature. When you win, its always your skill, when you loose, its always luck, or some other reason out of your control. İts like when my dad buys watermelon. İf it turns out to be a good one, he picked well. İf it turns out bad, then its wherever he bought it from cheated him. :D
      Nov 4
    • If your claim is that you found undocumented Facebook APIs that let you manipulate search/visibility/rating scores for your content then... that’s not great.
      Nov 4
  • Facebook / Eng
    T3chlead

    Facebook Eng

    PRE
    Google, LinkedIn
    T3chleadmore
    TC, net worth?
    Nov 3 4
    • Facebook dafu
      And YOE.

      Really for it to have been worth it you shouldhave outranked a similar effort career trajectory in a publicly traded company.
      Nov 3
    • Deloitte / Project PM007
      He made $3M from exits alone, I think YOE is 10+, not sure which listed company can give this much to a PM profile
      Nov 3
    • Amazon / Eng OlAl28
      Agree with FB, would be interested in hearing YOE.
      Nov 3
    • OP
      15 YOE. I grew up in the bay area so I have a lot of friends from high school and college. There are plenty of folks who have made more money at larger companies. I wouldn't have minded that path as well.

      For me, I didn't get the big, fancy internships in college. I had to get a bit more scrappy. My path is just one path. I think financially, I got pretty lucky to net out higher than most. In terms of knowledge and experience though, I think I have much more.

      For some of my engineer friends, they look at retirement defensively. There are always a new class of engineers who are better and faster. They'll have to differentiate by going down the manger track and most are. For product management, I like to think that we get better with age. Like fine wine. So I'm very confident in my continued outlook and value. I think I'm better off having some startup experience versus having none, is all.
      Nov 3
  • Amazon hrpOYt
    What are some questions you should be asking before joining a startup to gauge how successful or unsuccessful it might be?
    Nov 3 1
    • OP
      The people at the startup are you going to sell you hard and tell you what you want to hear. That's probably why you need outside input. I would do some due diligence on the management team, is possible. At the end of the day, you don't need to burden yourself by trying to predict winners -- if it's a great job for 2 years and you feel like you'll learn a lot, that's fine.
      Nov 3
  • what kinda engineers were the best to work with and what is your advice for engineers who work at big companies now but want to start companies later?
    Nov 3 4
    • OP
      Yea awesome question. Whenever I made a significant advancement in the product there was at least 1-2 engineers who were in it with me. Couldn't have done it without them.

      It seems to happen naturally. I pitch something that resonates. They're eager to make things happen. We're in the trenches and chemistry builds. We get a great outcome. When I became more of a manager, I do look out for these engineers. Ones who seem to do the work of 2-3 engineers or simply do what can't be done.

      I would love to start a company with these people. If you're an engineer at a big company, then I would pair with a non-technical person who seems to have unusual momentum, a great track record for shipped products, and someone you like spending time with.
      Nov 3
    • thanks man
      Nov 3
    • Intel / Eng mr_pleb
      Were these engineers rewarded appropriately for their efforts or you just used them to climb the ladder ?
      Nov 3
    • OP
      One was the 2nd engineer of the company and had even more to gain. What I could control is helping them get promotions and most are off doing pretty amazing things elsewhere.
      Nov 4
  • Zyzyxtech TimZuck
    $3M in exits doesn’t sound like a whole lot if you were an exec. Is this post-tax $$$?
    Nov 3 7
    • OP
      Both ended up being acquisitions. For one though, the main game plan and talk track was IPO.
      Nov 4
    • Amazon hoborvat
      It says 3B not 3M
      Nov 4
    • Zyzyxtech TimZuck
      Amazon, $3M for OP. That’s 0.1% of 3B, which sounds low for an exec. Mid career SWE would get that kind of equity. For execs, that number should be at least 1%, sometimes more.
      Nov 4
    • OP
      The first exit, I only got low six digits. The second exit is where I got seven digits. Like I said in a prior post, I didn’t enter the startups as an exec.
      Nov 5
    • Zyzyxtech TimZuck
      Got it.
      Nov 5
  • New qwvBE3
    I want to be a PM but I don’t have an engineering degree. Do you think that an engineering degree is important to have to be a PM?
    Nov 3 4
    • OP
      I don't think this has been a requirement for the past 5 years or so. My sense is that Google still wants technical more so than most companies. I think now the most valuable hard skill for PMs is SQL.

      Beyond degrees, the hard part about getting to PM nowadays is the sheer demand for the job. So there is a ton more competition and not a lot of supply. In the past 10 years, it's one of the top jobs that MBAs want afterwards. So get creative. Easier to move internally.
      Nov 3
    • Google OAoK43
      Most PMs I have seen at Google have non CS backgrounds - contrary to what they say!! You do not need a CS degree to be a PM.
      Nov 3
    • Dropbox / Product FDSh48
      Still need to pass technical interview to get in the door direct into PM tho
      Nov 3
    • Google prodpeep
      You may be in a different part of Google than I am. The PMs I know are pretty technical. The majority are BS CS + MBA. There aren't normally any coding interviews for PM at Google but there are a lot of product/business hypotheticals to gauge whether you'd be a strong generalist PM (and possibly also domain interviews). I've seen a lot of people rejected for not being technical enough; Google doesn't tend to like PMs that come from marketing backgrounds, for example, although there are always exceptions.
      Nov 3
  • Uber SufvDA
    How did you negotiate equity at these startups? Given your experience, what would you recommend people do?
    Nov 3 3
    • OP
      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.
      Nov 3
    • New psylow
      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 😔
      Nov 3
    • OP
      I have no idea what a "convertible note" is in the context of equity. I thought that term is used for borrowing money and loans.

      No equity for early employees + convertible notes sounds fishy. Why can't you get stock options? Most companies have at least a 10% employee stock option pool.

      I wouldn't worry about the specific title per se, but you do need to know where you stack rank compared to the other employees. Does the CEO consider you C-level material -- which means hire people under you, have you present at board meetings, be a member of the exec team? Or do they want to hire someone above you one day? That's basically what you want to figure out.
      Nov 3
  • Wayfair dCASBV
    What do you think about job-hopping every one or two years?
    Nov 3 1
    • OP
      One year is rough. Indicates that something might have been wrong. Two years is solid, three preferred. The people who seem to realize the biggest gains are those who work at a company 10 years with lots of career progression and leave a legacy. But obviously those opportunities are rare.
      Nov 3
  • AnchorFree / Eng 🍪 cookie
    How much equity a senior engineer can reasonably ask for, joining as employee number 20 to a startup that exists barely few years? And whether to ask for "options"or "shares"?
    Nov 3 7
    • AnchorFree / Eng 🍪 cookie
      0.05% means that on exit of 1b, you could get 500k? And an exit of 100m will get you a new Toyota Prius prime turbo? 😅
      Nov 5
    • AnchorFree / Eng 🍪 cookie
      Well if a manager gets 0.05% on average, then in my case it's probably 0.02% will be good. Ok great I'll know approximately what to ask if I'll calculate the total shares when they send me more info.
      Nov 5
    • Amazon SDE3Hire
      Yes, as OP said you need really big exit to get a ton back if your not founder / VP level higher.

      I know people who joined day 1 as engineers and got 1%. That's pre-dilution of many rounds of fundraising so it drops a lot.
      Nov 5
    • Amazon SDE3Hire
      @AnchorFree - The point was don't pay attention to %, pay attention to money value.

      % can vary a lot by where company is money wise and doesn't matter as it dilutes (only founders should watch this for voting right reasons).
      Nov 5
    • AnchorFree / Eng 🍪 cookie
      Haha! So I joined a startup in San Mateo, and got a 0.24% of total shares.
      They only had round A. They're about to announce round B soon, I wonder by how much it will get smaller, my share. Well, anyway the offer was badass on base as well so I'd join them even with 0 shares (it was largest offer of 5 places) so I'm happy
      Nov 12
  • Facebook anonmice
    Having trouble breaking into startups... I’ve been trying to transition and all I’m hearing is crickets from anything early stage enough to be interesting. As someone who has gone far in the industry: Any tips for breaking into the vc backed startup club? How did you find your first notable women hires at the two start ups? From my experience thus far I’m guessing women get hired on personal referrals at a higher rate vs applications. But, hey, maybe it’s just as tough for men.
    Nov 3 6
    • Love this question! So true. Most of the startup I see don’t have any women at early stages. Just a quick browse on angel.co shows that.
      Nov 3
    • Facebook anonmice
      Yeah, just not hearing back. I’ve applied to about 20 promising, funded startups. For each opportunity I’ve been meticulous; Carefully researched the company and wrote a thoughtful cover letter that highlights the ways my experience and perspective complement their unique goals. I’ve even been reaching out on LinkedIn to try to start a conversation with employees. Complete radio silence. Not sure how to go about meeting the right people to position myself for referral. Perhaps my location may be part of the issue. I do have to say that if you cruise through Andreesen backed startups there isn’t a strong female PM presence.
      Nov 3
    • Facebook anonmice
      Thanks for the AMA, btw. Very cool of you!
      Nov 3
    • OP
      No problemo! I don't know if cover letter are effective for startups. For resumes, it needs to pass the 6-second test. The response rate from applying to jobs is pretty terrible. Something like 10:1 or 20:1 even for the best candidates. Typically you need someone on the inside or a friendly on the outside to help point out your resume. This is where your network helps you get the foot in the door and it's your job to bring it home.

      Location might matter. It might be easier for you to transfer internally to the location first. You basically want to remove as many variables as possible. Startups need people who can hit the ground running. Not a lot of time to train.
      Nov 3
    • New / Sales youweakie
      Can you provide some bullets of your resume that you think is targeted towards the PM roles you've applied to?
      Nov 3
  • Microsoft / Other : 🐧
    1. Why haven't you started your own company?
    2. How important has your network been?
    3. Did you have mentors? Where did they come from? How did your relations look like?
    Nov 3 2
    • OP
      1. I'm not sure. From most founders that I talked to, some feel like they were destined to, or had no other options, or the stars aligned. None of these were true for me yet. But I might in the future!
      2. Very important in subtle ways. You develop a reputation with the people you work with. In the future, they are your references but more importantly they are secret, backdoor references for the hiring team. If you get the job, you usually hear about who those references are. I like to treat people with respect (though I've made mistakes), and I've netted out in the positive direction here. Some of my friends have gone to top MBA programs, I think they're network is awesome and it will serve them well for a long time. Jealous of that at times.
      3. Yes. Co-founders of the startups. First or second employees at the startup. Leaders at the larger companies I've worked for. But most importantly early on in my career were some of my peers. I would try to "steal powers" from my peers who I noticed were the best at X. That gave me the necessary fundamentals to do higher-level work. To this day, I still talk to 4-5 mentors now as friends. At startups, you go to hell and back -- it builds a connection like no other.
      Nov 3
    • Microsoft / Other : 🐧
      Thank you, kind Blind soul
      Nov 3

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