Phil Santoro & David Kolodny of Wilbur Labs: “Doing both is necessary, and our teams do both on a daily basis”

A second great piece of advice came from one of our advisors, she said early that as we grow we need to refrain from hiring people who are too high level and can’t do any tactical work. We have absolutely seen how critical it is that startups hire people who can do both. There’s a […]

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A second great piece of advice came from one of our advisors, she said early that as we grow we need to refrain from hiring people who are too high level and can’t do any tactical work. We have absolutely seen how critical it is that startups hire people who can do both. There’s a common belief that someone is either good at high-level strategy or good at detail-oriented execution. This couldn’t be more false. Doing both is necessary, and our teams do both on a daily basis.

As a part of our series about business leaders who are shaking things up in their industry, I had the pleasure of interviewing Phil Santoro and David Kolodny.

Phil Santoro and David Kolodny co-founded Wilbur Labs, a San Francisco-based startup studio turning bold ideas into industry-leading companies. Wilbur Labs identifies big customer pain points and builds businesses to solve these problems. Since 2016, they have built and invested in 13 technology companies, including VacationRenter, Vitabox, Joblist, and Barkbus, and plan to launch several new companies over the next year.

Thank you so much for doing this with us! Before we dig in, our readers would like to get to know you a bit more. Can you tell us a bit about your “backstory”? What led you to this particular career path?

David: Phil and I met the day we both started at Google back in 2013.

Prior to joining Google, Phil built FreeForums, a free forum hosting platform. He founded the company while in high school and by 2007, FreeForums was one of the top online destinations globally, receiving over 125 million monthly pageviews. He became the first student at his university to rent two dorm rooms — one for his office and servers. Phil sold FreeForums to a public company his second year of college.

I studied business at the University of Michigan before joining Google. During my time at school I worked at various start-ups including Aereo, a technology company that let subscribers view live TV through tiny remote-controlled antennas, and co-founded Slinky Charity Group.

At Google, we both were on the ads side and moved around together to various teams. While we were there, we saw company after company moving slowly, and very manually — particularly on the growth side. We recognized this was mainly driven by organizational silos, lack of automation technology, and overall risk-averse decision making. This was not an industry specific problem, and something we thought had to be addressed from the very beginning of any company’s journey. We knew there was a better way to build companies, and that we could solve bigger problems by focusing on how companies are built, rather than just growing one single idea. Three years in, after brainstorming ideas for about a year we left to start a startup studio, Wilbur Labs, to rethink how companies should be built.

Can you tell our readers what it is about the work you’re doing that’s disruptive?

Phil: On the studio side, building a company is typically a rare, one-time event. Some people even refer to building a startup as trying to ”bottle lightning”. At Wilbur Labs, it’s a repeatable and systematized process. Turning a bold idea into a business — over and over — is what we do. This has required breaking down, rethinking, and rebuilding every step required to launch a company. We operate very differently, which has allowed us to build a portfolio of multiple companies that grow at a faster and more efficient pace than traditional companies. VacationRenter is a good example of the results of our unique approach. We launched VacationRenter out of the studio in 2018 and in its second year they did 600 million dollars in gross bookings. Zero to 600 million dollars in gross bookings in two years is unheard of, and made VacationRenter one of the fastest growing travel companies ever.

Aside from our unique approach to building, what’s equally important to us is the scale of the problems we solve. We have a studio thesis which we use to guide our investments in building new companies. There are multiple points in our thesis but the most important point is that we want to solve big problems where we can build an advantage that allows us to better serve customers. For example we went into travel and built a better way to find vacation rentals, RVs, and hotels with VacationRenter. In eCommerce we built Vitabox as a way for households to order everyday essentials at better prices. In employment, we rethought the job search process and built Joblist using personalization and collaboration at its core. In pet care we have Barkbus which is making mobile grooming the new norm for pet parents and their dogs. These are just a few examples of how we have taken this approach and rebuilt industries. The common element here is that these were massive consumer problems that weren’t being truly solved by the legacy companies. We came in, rebuilt the industry how it should have been built today, used the latest technology available, and grew very large companies as a result.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Phil: When we first left Google in 2016 to start Wilbur Labs, David and I worked from my apartment for the first six months. We refer to that summer as the “lost summer” because we worked long hours and I don’t think I saw the sun for weeks at a time. Since David came to work at my apartment, I didn’t have a reason to ever leave. That fall when we both happened to get routine blood work, we both had severe Vitamin D deficiencies. Vitamin D deficiencies are common, but ours were dangerously low.

The lesson here for me is that optimizing your mind and personal health is just as critical as optimizing any part of your company. Since day one, we have focused on solving big problems and building large sustainable companies over a very long period of time. Staying healthy and productive over a long period of time — at the pace we work — requires being smart and disciplined on health and wellness. This experience kicked off my interest in biohacking, and I now try to optimize every part of my routine and day so that my health can support my lifestyle.

To this day, we also have a Vitamin D complex at our workstations. At Wilbur Labs we believe mistakes are okay, as long as we avoid making the same mistake twice, or make careless mistakes that could have been avoided with smarter planning. This is a great example of a mistake that we only made once.

We all need a little help along the journey. Who have been some of your mentors? Can you share a story about how they made an impact?

David: Our primary focus is taking ideas from zero to one, and building them into a big business. We do not have deep expertise in every industry we operate in, so we rely on several advisors and mentors.

Chris Fong has been one key mentor to Phil and I. Chris worked at Google with Phil and I, left shortly before us, and started the community, which includes more than 7,000 current and ex-Google employees working together to help each other in the startup ecosystem. Chris, and the network, have helped us build the Wilbur Labs community, recruit key hires, as well as make strategic decisions. In addition, Chris has helped us connect with several other ex-Google employees who have now become advisors.

We believe that advisors and mentors play a critical role when building a business, and are super appreciative to everyone that has helped us along the way.

In today’s parlance, being disruptive is usually a positive adjective. But is disrupting always good? When do we say the converse, that a system or structure has ‘withstood the test of time’? Can you articulate to our readers when disrupting an industry is positive, and when disrupting an industry is ‘not so positive’? Can you share some examples of what you mean?

David: At its core, “disruption” means change. It is true that change can be positive or negative, but in almost every case, change is inevitable, so it should not be feared just because it is new. In addition, change can sometimes be seen as “not so positive” in the short-term, but over the long-term, I believe that most industries arc towards positive progress.

We built Wilbur Labs with this in mind, and take a very long-term view for any problems we are working to solve. By focusing on large problems over a long long period of time, we can drive significant positive change. There may be hiccups along the way, but you are able to chip away at your vision piece by piece.

Phil mentioned Joblist earlier, and they are one good example of this. In employment, the process for finding a job online hasn’t changed in 10 years, yet there is a ballooning unemployment crisis and people are in need for easier ways to find a job. Joblist recognized this, and disrupted the industry by focusing on personalization and collaboration — two key components that are missing from the majority of current job searches. By taking the long-term view and focusing on substantial industry problems, we know the team is able to build solutions that can withstand the test of time.

Can you share 3 of the best words of advice you’ve gotten along your journey? Please give a story or example for each.

Phil: I’ll share two and David can share one. One of the best pieces of advice I received is to get customers to vote with their wallet. Early on when you have an idea and start talking with people, everyone will be excited and will say it’s a great idea. This is especially true if you know them well. However, if you go back to them with a built product and ask them to pay for it, chances are very few would. This couldn’t be more true and we have adopted and refined this as a way to find product fit. We strongly believe that getting customers to vote for products and services with their wallet or with their time is by far the best measure of product-market fit. If customers won’t spend time or money on your business, then you either have some other issues with the product or with the problem you are targeting.

A second great piece of advice came from one of our advisors, she said early that as we grow we need to refrain from hiring people who are too high level and can’t do any tactical work. We have absolutely seen how critical it is that startups hire people who can do both. There’s a common belief that someone is either good at high-level strategy or good at detail-oriented execution. This couldn’t be more false. Doing both is necessary, and our teams do both on a daily basis.

David: A mentor of mine shared advice that I still think of often: say no. When starting a company, or running a business, it is easy to get distracted by lower priority opportunities or things that detract from your ultimate vision. While it is important to say yes to the right things, I think that most of the best operators and disruptors end up saying no much more often. In fact, if you aren’t often saying no, it almost certainly means that the scope of your team is growing too broad and that you are not collectively operating as effectively as you could be.

We are sure you aren’t done. How are you going to shake things up next?

Phil: Wilbur Labs has two primary objectives: building new companies and supporting our portfolio. For our portfolio, we continue to work closely with each leadership team to manage through the pandemic. This is a very difficult business environment, and we think there will be a lot more pain to come.

In terms of building new companies, we could not be more excited about our next batch. We are evaluating all our ideas through what we call the “COVID-lens”. What this means is that we aren’t interested in any of the short-term effects of the pandemic. Instead, we’re thinking far out and projecting what consumer trends or behaviors are going to change long-term.

We recently greenlit a new company in the insurance industry, and have two more ideas moving through our research phase. This is a difficult business environment, but a great time to solve new problems and build a big business as a result. We have always been focused on the long-term and this is a perfect time for us to make some long-term investments.

Do you have a book, podcast, or talk that’s had a deep impact on your thinking? Can you share a story with us? Can you explain why it was so resonant with you?

Phil: Only the Paranoid Survive by Andy Grove has been one of my favorite business books since first reading it a few years ago. With the recent business environment created by the COVID-19 pandemic, the ideas presented are even more valuable.

Andy argues that in a crisis, or Strategic Inflection Point as he refers to it, the old way of doing things goes out the window. The companies who embrace this change, win market share and emerge stronger than before. This is the exact condition that exists today, and why aspiring entrepreneurs should be optimistic about building companies during this time.

David: Funny enough, the book that stands out most for me is also by Andy Grove! It is High Output Management. So many business and management books focus on theory and aren’t as directly applicable as you’d like them to be. High Output Management is the opposite. Andy goes through high-level principles, but also how they are directly put into practice for any level of manager. There is so much to get out of this book that I often go back to reread different sections.

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

David: A favorite life lesson quote I try to live by is from my dad. He says that “you learn nothing in life if you’re the one doing all the talking.” We start several companies per year, and are always learning about new ideas or industries. When you’re learning about a new space, it is infinitely more effective to listen to others, than to spend time talking. The same is true when working with a team, or making any strategic decision. Information is everything when making complex decisions; the only time you will be gaining new information is when you aren’t doing all the talking.

Phil: That is a great quote! One of my favorite quotes that I live by is from George S. Patton: “a good plan, violently executed now, is better than a perfect plan next week.”

As a startup studio, we are big into planning and structure. Creating the optimal structure and process to build and scale companies is what has allowed our companies to grow faster and more efficiently than traditional companies. Having said that, we also know that there is no such thing as a bulletproof plan. As a business takes off, you will need to constantly adapt and change your plan. The best entrepreneurs are comfortable being uncomfortable — adapting as they go.

I really like this quote from Patton because it acknowledges that you still need a good plan — some founders incorrectly think that if you take the time to plan you aren’t moving fast enough. However, Patton says that launching early with a good plan, executed well, far exceeds waiting to create the “perfect plan”.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Phil: Technology and startups can’t solve all the world’s problems, but they can solve a lot of them. Now more than ever, we really need people to step up and build the next generation of companies tackling some of the world’s biggest problems. There are a lot of unknowns right now, and that can seem scary, but this is the best time to start a company — ever.

Today, industries and trends are evolving much faster than ever before. There are new consumer trends, which would have matured slowly over 5–10 years, fully maturing in a matter of months. This creates an opportunity for entrepreneurs to sit down, think about what the future will look like, and build a company for that.

I can think of a handful of problems now, which are solvable, and if solved would make the world a better place for hundreds of years. This is the opportunity right now, and what’s at stake.

How can our readers follow you online?

Phil: I’m most active on Twitter and LinkedIn. You can also read more about Wilbur Labs, the startup studio and our portfolio, at We recently launched a new series of “Blueprints,” where we share some of our learnings and approaches building multiple companies over the last few years.

David: You can follow me on LinkedIn.

This was very inspiring. Thank you so much for joining us!

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