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What are your thoughts on three top traits that make up a successful product manager with success measured as executing on a product roadmap and delivering on your metrics?

1. Communication, communication, communication
2. Servant leadership – you serve at the behest of the org, even as a Head of Product
3. Be comfortable w conflict – great products are born out of collaboration but not consensus.

You can’t need/want everyone to agree but you are responsible for helping everyone understand why decisions are being made and empower the right people to make the best decision they can make at the time.

What’s the one thing you didn’t know, but wish you had when making the transition from product to VC?

To be honest, there wasn’t anything specific – I was fortunate to already know that venture isn’t a “player/coach” role – ie you don’t do venture because you love building products.

That’s the thing which I believe trips up most PM->VCs. The one thing I knew intellectually but couldn’t truly feel until I got into the industry was how long the cycle times are for true feedback.

I went from being able to run percent tests over night to having 5-10 arcs in terms of company outcomes.

What was it about Anchor that made you excited as an investor?

Team Team Team – the founders had a specific vision for how audio was going to be a future platform.

Their past product history suggested they knew how to keep experimenting around an insight until they found PMF.

Think of it as someone holding a cube and rotating that cube until the correct side was market-facing. That’s what we got the sense of – they had the right cube and were skilled in turning.

What are your top skills that you developed as a product manager that you now actively leverage in your day-to-day as a VC?

Two things come to mind. First, empathy for the building journey. no matter how old or out of date my specific product experiences become – and they do age quickly! – I’ve been able to maintain the excitement, and empathy for what it feels like to build something which doesn’t yet exist.

I’ve never been a founder, so i’ll never know 100% what our founders are going through (well, I guess we founded Homebrew so there’s some similarities there), but what I think is even more of a bond is the act of building.

Second, willingness to create something that doesn’t yet exist. We’ve backed plenty of teams who are working on new spaces – not the 2.0 or 3.0 or 4.0 of a problem space but the 1.0. To me that’s very exciting and very much in-line with how we tried to approach product building in general.

What’s the biggest lesson learnt/setback/problem/failure you see in PMs trying to transition into a VP of Product?

Great question and one that’s very personal to my own experience. Where i messed up once was immediately trying to do more myself, versus get the org right (structure, skills, roles).

Also failing to transition from communicating primarily w prod/eng/design to realizing you need to spend much more time at the cross-functional level, building trust and relationships.

What are the qualities of the best engineers that you have worked with? Have you noticed a pattern in how they developed themselves?

Re: best engineers – there are lots of different paths to engineering excellence and what type of product you’re working on also matters a lot.

For the consumer products I’ve worked on one thing i’ve always noticed in the best engineers is that they seek to really understand the users, or have a very intuitive feel for how the product will be used, versus just focus on the technical requirements or becoming over-enamored with the elegance/coolness of the technology itself.

Looking forward, are there technologies or unique uses of technologies that you’re geeking out about?

There’s a ton of stuff which excites me. Camera as Platform is interesting and has potential on both consumer and enterprise side (we’re investors in a startup called CameraIQ that’s working on this).

Robotics which augment/enhance humans – i don’t literally mean iron man (although that would be cool) but rather fit into workflows alongside people – we’ve got one in the agriculture space here that has potentially to really impact the food supply chain.

What were some of the best career / professional lessons you took away from helping to found Linden Lab + Second Life?

I wish i had enjoyed it more in the moment. That last year or so i was there, i was really stressed because things were tough and i thought that if the company wasn’t an A++++++ hit, my career would be a failure.

In retrospect, it’s been successful (albeit not to the degree we hoped but 18 year old company that’s profitable is pretty cool) and working on such a neat, tough problem with a very smart team is also something which doesn’t happen all the time.

Could you speak a little bit on product manager and sales relationships? What is your past experience with sales and the PM interactions?

When I worked on AdSense, this was great. At Youtube sometimes I struggled with this.

A good salesperson is always going to push aggressively and advocate for the client(s), but i think a good sales executive is going to work with product to understand what decisions/priorities are and then hold the product org accountable but also protect the product org from things outside of that scope.

There’s likely always going to be some tension between product and sales, but leaders of both trusting each other and knowing that you’re all working together to create a long-term valuable company, is essential to day-to-day functioning.

Get sales VPs to give you representatives from their org to service on XFN project teams and make those folks accountable for rounding up sales feedback + bringing decisions make to their org (vs just making it the PM responsibility).

From all your Google/YouTube experience, do you have any guidance on how to transition a legacy system to something more forward thinking? At my org., we seem to have reached a point in our market where any app changes irritate about half of the people, and the other half want even bigger changes.

Try to communicate the vision, the reasons behind decisions (as honestly as you can), what KPIs you’re optimizing for and figure out ways to bring these messages into your user communities outside of just a one off company blog post.

Then also get comfortable with the fact that not everyone will always be happy with any change.

That’s fine but there’s a difference amongst people being angry about change in general, small percentages of users who don’t like the specific change, anger which comes from violating the spirit of the trust/bond you have with them, anger around dishonesty with regards to why decisions are being made or sometimes, just plain old wrong decisions which need to be revisited.

Were there any product feature experiments you ran at YouTube that led to unexpected results?

Yeah, so one i recall was shortly after we launched Personalized Recommendations. https://hunterwalk.com/2014/04/16/context-matters-lessons-learned-from-youtube-personalized-recommendations-and-why-this-matters-for-twitter/

What are your top motivations as a VC fund? Do you  pressure companies to have an exit within a 24-48 months range and get access to more liquidity? I’m trying to figure out what’s the contribution of a fund in building a solid product with a great market fit.

Noooooooo, most companies that exit w/in 2-4 years post-seed are outright failures or haven’t fulfilled their full potential. We’re fully expecting our most successful investments to take 8-10-12 years for an exit. here’s how we work with them: https://venturegeneratedcontent.com/2017/07/19/how-we-work-at-homebrew/

What do you think are the characteristics that are unassumingly different for Enterprise Product Management?

This is via observation more than any personal experience. Generally, enterprise PMs are more process-oriented because (a) their roadmaps are set further in advance, (b) communication and support of paying customers can be different than b2c stuff.

Enterprise PMs are also more xfn (cross-functional) in nature because most enterprise companies scale the org w growth (sales, CX, etc).

When you have to do your own user research for a new product, what is the best way to reach data-driven conclusions with very little data?

There’s so many ways. First, make sure you start w clear hypotheses that you’re trying to confirm/disprove, rather than just asking people to “react” to something.

Then you can use everything from casual conversations with people/target customers/etc to mechanical turk etc to test and gather very specific data.

What you’re trying to answer are things which are binary, not things which can be optimized over time.

What are your tips on balancing a product review + release process that’s thorough, but also allows for moving quickly + avoiding bottlenecks at a small startup?

The eternal struggle! Ok, I believe in getting things correct upfront and then managing to milestones, not micromanaging product teams.

What’s important to get right upfront – hiring, prioritization, KPIs that you want to optimize for.

If you can do that, then specific product review/release process can be set up against milestones and asking appropriate questions at those milestones as you go from: early in the project (what’s the minimum amount of work we can do to validate these assumptions, etc) to medium (how is the team doing, is the spec still correct, are we on schedule, do they need more/fewer resources) to final (is it ready to release, how are we going to support/manage/measure this change).

Too many companies over-anchor on control, micromanaging, etc which in my mind are rarely issues with the specific project and more meta-issues on people, the goals, the leadership.