Who is Boris?

I started my tech career in mid-1990s NYC, back when it was called Silicon Alley, where I was lucky to be part of some notable firsts: the first website offering college credit online, the first app to order a cab through a website (should’ve stuck with that one!), and the first online voting platform.

Later, I set up shop on a virtual island in Second Life, where I worked with the UN, Yahoo, and IBM on their own virtual firsts. When smartphones and social media brought the virtual world into real life, I built a location based favor exchange followed by several apps for superfans of TV shows, music, and sports.

While I was a decent software engineer, I thought I had a shot at being a world class product manager, something I’m continuing to strive for today as director of product at a well known click and mortar retailer inventing the future of omni channel commerce and in-store tech. I am also working on a side project in cryptocurrency trading and trying to stay on the right side of the coming AI explosion. I’m a proud graduate of the MIT Media Lab and live in Ithaca, NY, with my wife, two kids, and a giant tortoise who keeps things interesting.

We sat down with Boris to find out a little more about his approach in 2025, and why start-ups in particular make amazing projects.

‍Projects and founders:

How do you pick projects?

I look for three legs:

1. Is it interesting/important/motivating enough for me to stick with for as long as it takes to follow through
2. Will it make my peers and friends proud of me or even better will some of them come along for the ride
3. Will I earn enough to achieve my family’s financial goals

Are start-ups a different beast?

I have worked primarily for startups during my career and love that energy. There is nothing like building something brand new, sometimes having to invent even the language to describe it. Of having the humbling experience of getting your work into the hands of real users and celebrating the win when some part of what you built dazzles them! This happens  in larger companies as well of course, but almost by definition the more cutting edge your work is in a large org, the more deminimis an impact it is likely to have (at first). 

What's the most important thing to look for in a founder?

A startup should not run out of time or money. There are many paths: wealth, clarity of vision, persuasion, charisma, genius, etc – the founder has to credibly be able to wield time and money.

What's the most important thing you can give a founder?

It depends on the situation, but generally it is one of three things: 

1. Creative challenge: establish enough trust with the founder that I can help them validate/question their assumptions and clarify or sometimes entirely remix the vision. This is often a hard road and I need to be ready to walk away if I can’t make an impact.

2. Scrappy/Present/Hacker/Politician mode: get it done in a non conventional, wacky and creative way. Hack together existing systems to get uncommon results, turn on the charm, use freelancers, experts, guerillas, open source etc to accelerate the path to value. Do whatever it takes to marshal the available resources into a product advantage. I personally find this to be very satisfying.

3. Expertise and team building: I am a subject matter expert in mobile app development and app stores, web development platforms, experimentation and measurement platforms, martech, etc. I know how to conduct user research and do market research quickly, I also know a lot of people in the industry and know how to recruit great product managers and designers (I think that’s how I scored this interview!). If the founder doesn't come ready with these resources, I am providing a huge accelerant.

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Product teams / product space:

What's the most important cultural aspect of a product team?

Technology doesn't solve problems, the people that build the technology solve problems. It’s kinda cliche, but you want to work with trustworthy people. As product people our job is to make decisions, drive consensus and take every opportunity to lead. This can only happen in an environment of trust for any length of time required to build something significant.

If you could take a permanent piece of real estate on a product manager's sprint board, so they saw it first thing everyday, what would it say? (If helpful, it could be a motivational message, an instruction)?

Talk to your users, use your product, repeat.

What are the worst recommendations that you hear in your sector or line of work

"If the stakeholders are happy, the customers will be too."

I don’t know that this is ever given as advice explicitly, but I’d say it is the most common trap every PM I know falls into regularly. It’s easy to give way more weight to the input of the people who deposit the money into our bank accounts than the people who pay us.

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Quick(er)fire:

Generalist v specialist? 

I only hire people who have done “it” before. At least one of the “it”s that need doing. In many cases you can't get a specialist  for everything you need, so learning the thing you have a gap in should be the only new thing the team is expected to learn.

‍Data v Instinct?

I live by this quote from Jeff Bezos:

‍“When the data and the anecdotes disagree, the anecdotes are usually right. It's usually not that the data is being miscollected. It's usually that you're not measuring the right thing.”

‍Agency, studio, in-house?

An agency will get you into the game fast if you’re starting from 0, but then you don’t usually need me at that stage. Studios are great to bring in at the beginning and for a shot in the arm every once in a while. I personally like to work with inhouse designers who are the most vested and hopefully familiar with customers and users.

‍Tools - what's your day 1 toolset? (Does it change?)

• Infinite whiteboard – currently Lucid Charts
• Kanban Lists – currently Teams
• Collaboration OS – currently Teams
• AI Prototyping - Replit
• AI Ideation - ChatGPT

‍What's the thing in your work set-up that you bought for $100 or less that had a big or surprising impact?

Dumbbells. I lift while I am on calls. No more excuses.

‍What are you terrible at? And wish you could be better at?

Design. I wish I could make my presentations look better on my own. Hopefully AI will make this easier, but as of now its still not where I want it to be.

‍What's your best / favourite question to ask in an interview (job)?

It’s a follow up question, when a candidate answers a question with some outcome. Like, “we learned that only teenagers liked x” and then I’ll ask them: “what surprised you about that?” It helps me gauge how thoughtful a person is.

‍What sort of products do you like to work on?

I like to work on products that use new technology or solve existing problems in a new way. I especially like to work with multi device/service technology. Like when a phone interacts with a different device like an ebike, or something has to be scanned or paired or a message is triggered that unlocks a special mode on a user’s device. I have also recently been interested in conversational interfaces again and passing users between smart ivr, human and text interfaces.

‍What wouldn't you like to be doing?

Project and program management.

‍How do you get into product? (Purposely ambiguous)

When I got into product in 2011 it was a relatively new field and I found I could be more creative than I could be as an engineer, but still stay close to the tech.

‍What's still happening that amazes you in the workspace? / What is fundamentally broken and keeps you awake at night?

Some flavors of the following dysfunctions are rampant even though everyone knows they are maladaptive:

This doesn't happen everywhere of course, but it puzzles me how much inadvertent influence slow/dysfunctional engineering organizations have on product outcomes. When a business is willing to accept months of delays because of “engineering”, those engineers become the defacto CEO because they are dictating the strategy now.

The HPPO doesn't talk to the customers/users

Marketing and product are poorly coordinated such that either marketing can’t promote what the product actually does or has undue influence on the product such that what they are able to communicate shapes what is being built.

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