Phil Santoro & David Kolodny of Wilbur Labs: “Let real-time data drive marketing decisions ”

David: This is a great follow-up to the question on branding because customer experience and branding are so interdependent. Building a wow! customer experience is a process reliant on identifying gaps, and scaling solutions to as many customers as possible. Talking to customers, analyzing product data, and consulting with industry experts, are all critical avenues […]

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David: This is a great follow-up to the question on branding because customer experience and branding are so interdependent. Building a wow! customer experience is a process reliant on identifying gaps, and scaling solutions to as many customers as possible.

Talking to customers, analyzing product data, and consulting with industry experts, are all critical avenues to identify how to improve your product. It’s important to seek out critical feedback and not just talk to fans who are likely to applaud you.

The key differentiator for those creating wow! customer experiences are not just collecting these insights, but being able to translate them into scalable applications. If you can establish a process of capturing insights, building them into a product, and scaling them to your customer base, you will constantly surprise and delight your customers by always improving.


As part of my series about the “How To Take Your Company From Good To Great”, I had the pleasure of interviewing Phil Santoro and David Kolodny. They 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 joining us in this interview series! Before we dive in, our readers would love to “get to know you” a bit better. Can you tell us a bit about your ‘backstory’ and how you got started?

Phil: Thank you for having us. My journey as a founder started early. I founded my first tech company when I was 14, and sold my second business to a public company in college. After college I went to work at Google, where I met David. We both started on the same team, on the same day, back in 2013. We moved teams multiple times and sat next to each other for over two years. We realized early on that both of us wanted to start a company, since I had started a company before Google, and David had been working on several start-ups. David and I had a recurring dinner every week where we would grab food at the same restaurant and brainstorm startup ideas. We ultimately realized we wanted to solve problems across multiple industries, and decided to launch a startup studio.

Can you tell us a story about the hard times that you faced when you first started your journey? Did you ever consider giving up? Where did you get the drive to continue even though things were so hard?

Phil: Wilbur Labs is a startup studio, which means we are a company that builds companies. The biggest challenge for us back in 2016 was that there weren’t any wildly successful startup studios. The business model hadn’t been cracked and there was no playbook we could follow. We are very different from VCs and accelerators, in that we believe operational support and shared resources are much more valuable than just capital alone.

This meant that we had to rethink the best way to build companies, at the same time we were building our first batch of companies. We had to find market fit for our studio model at the same time we were finding fit for the companies we were building.

When David and I talk with founders, we always ask if they want to spend the next 5+ years of their life working on this. That is an important question, because it really does require at least 5 to 10 years to build something material. This long-term mindset helped us through every challenge, and has continued to be a major driver for us to this day.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lessons or ‘takeaways’ you learned from that?

David: Right after we left Google, Phil and I wanted to go away to brainstorm ideas outside of the office — which was Phil’s living room at the time. After reviewing some options, we decided on a trip to Yosemite. The trip was amazing, but we soon realized that WiFi wasn’t so easy to come by there. When we weren’t hiking or exploring Yosemite Valley, we were driving around to different hotels trying to find a public WiFi connection from our car in the parking lot so we could brainstorm and research some of our initial ideas.

The takeaway: whenever you are going on an offsite, always confirm WiFi access and speeds.

What do you think makes your company stand out? Can you share a story?

David: What makes Wilbur Labs standout is the time between when we identify a problem, and how soon after we can rapidly scale a company solving that particular issue. We are singularly focused on taking companies from 0 to 1. By focusing on that, we are able to take ideas and scale them into market-leading companies at an incredible rate that isn’t possible without a model like ours.

One example of this is VacationRenter — we launched the company in 2018, and only one year later announced generating over half a billion in gross booking volume. This is the fastest growth in any travel company we know of, and it would not have been possible without the approach and shared resources of the studio.

Which tips would you recommend to your colleagues in your industry to help them to thrive and not “burn out”?

Phil: It’s important to enjoy the process and not try to rush to some destination. Instead of stressing about a milestone or exit, take a multi-year view and work towards that. That doesn’t mean that you aren’t pushing as hard as you can in the short-term — because you are — but it does mean that you are thinking long-term. This helps remove some of the short-term stress, which often leads to burnout.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story?

David: Phil and I often reflect on all the mentors and advisors who have helped us along the way. We focus on taking ideas and building them into big businesses. We operate across several industries, so we rely on several advisors and mentors who do have expertise in other areas.

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 Xoogler.co 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 Xoogler.co 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.

Ok thank you for all that. Now let’s shift to the main focus of this interview. The title of this series is “How to take your company from good to great”. Let’s start with defining our terms. How would you define a “good” company, what does that look like? How would you define a “great” company, what does that look like?

Phil: I believe a “good” company is a company which has found a place in the market, creating value by helping solve a problem for customers. A good company takes care of its customers, employees, investors, and partners. The world needs good companies to continue solving problems and taking care of customers and employees in a sustainable way. There’s nothing wrong with being a “good” company.

Now, a “great” company does all of that and more. A great company has a larger impact both in terms of the importance of the problem they are solving, and the scale in which they impact people. A great company has the potential to have a positive impact on the world around it, by helping build the future. A great company has a positive impact on its community and the world, in addition to its customers, employees, shareholders, and partners. Great companies aren’t concerned with short-term objectives, but instead want to solve large problems and drive positive impact over a long period of time.

Based on your experience and success, what are the five most important things one should know in order to lead a company from Good to Great? Please share a story or an example for each.

Phil: I can share a few and then David can jump in.

Solve problems you can solve better: this is a big one, and at the core of our studio thesis at Wilbur Labs. Building a great company takes a combination of extreme focus from people who can solve a problem better than others, and dedication over a very long period of time. If you aren’t committed for 5 to 10 years, or don’t think you are the best person to solve that specific problem, then it likely makes sense to pick a different direction.

Create a plan: if you feel stuck going from good to great, go back and create a new plan based on what you know. Having a solid plan is very important for making the jump. This doesn’t mean that you can follow this plan completely because there’s no such thing as a bullet proof plan. However, moving forward with a plan is always better than going in with no plan.

Adapt: the best entrepreneurs are comfortable being uncomfortable, adapting as they go. Even with a great plan, you will always have to adapt and evolve along the way. This won’t change no matter how successful you are.

David: All great points! Adding a couple.

Learn from experiences and mistakes: when leading a company, making mistakes is an inevitability. How you react and learn from mistakes is optional, and it is critical to apply learnings from mistakes in order to improve overall organizational effectiveness. Flying offers a great perspective on this — the only reason flying is safe today is because of the mountain of mistakes and learnings that have come before. Pilots follow checklists and protocols that have been battle-tested and improved over all the decades of flights that have come before them.

Execution is everything: all the above points are worthless if you don’t execute and show up everyday. One of our values is inspired by George S. Patton’s quote where he says, “A good plan violently executed now is better than a perfect plan executed next week.” Planning is critical, but is not a substitute for action. Going from good to great requires a tremendous amount of output, and execution is the driving force for how you will get there.

Extensive research suggests that “purpose driven businesses” are more successful in many areas. Can you help articulate for our readers a few reasons why a business should consider becoming a purpose driven business, or consider having a social impact angle?

Phil: As I mentioned earlier, it’s very difficult to build something great unless you dedicate 5 to 10 years towards that goal. It’s also very difficult to dedicate 5 to 10 years to something that doesn’t have a purpose bigger than just generating revenue. There are many ways to define purpose driven business, the bottom line is that working towards driving positive change is what will keep you going long-term — not quarterly revenue targets.

What would you advise to a business leader who initially went through years of successive growth, but has now reached a standstill. From your experience do you have any general advice about how to boost growth and “restart their engines”?

Phil: At a certain point, some organizations generate enough drag that it can’t keep climbing. This drag could be recurring work that takes up everyone’s time, outdated processes and structure, acceptance with “this is the way we have always done things,” not understanding the current market conditions, etc. Getting back to basics and focusing on execution towards your goal can be productive. This is easier said than done, and requires every person in the organization to take ownership and embrace change.

Generating new business, increasing your profits, or at least maintaining your financial stability can be challenging during good times, even more so during turbulent times. Can you share some of the strategies you use to keep forging ahead and not lose growth traction during a difficult economy?

David: 2020 has certainly been a great example of an unpredictable, difficult economy. At Wilbur Labs, we focused on a couple key things to maintain and increase growth traction at each of our portfolio companies.

Let real-time data drive marketing decisions — in ordinary times, looking at historical snapshots can be very helpful and informative. In the course of a global pandemic, historical data is largely worthless because whatever happened last month is not necessarily an indicator for what is happening today or tomorrow. Since the beginning of the year, each Wilbur Labs portfolio company has worked on building dashboards with real-time metrics on every facet of each business to ensure that decisions are being made on the most relevant data possible. Though trends are smoother now than they were in March and April, we are still seeing rapid customer behavior changes happening on a daily basis, and real-time data loops have directly contributed to greater marketing efficiencies.

Leverage automation to respond to behavior changes. For the first time in modern history, we are seeing trends, like global eCommerce adoption, that ordinarily would have taken five years occur in five weeks. With such rapid change, it is impossible for manual processes to keep up. By utilizing automation wherever applicable — and connecting it to the real-time data described above — we have been able to ensure that our portfolio companies are maximizing every opportunity available to them.

In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?

Phil: One of the most underestimated areas is understanding the role of a founder. Building a company is very different from building a product. There is a mountain of other work that requires the same exceptional excellence as the product itself. Not only this, but the role of a founder is constantly changing. The role David and I had at the beginning, when we were on my couch building our first product, is very different from the role we had once we started hiring our team, which is very different from the role we have now.

I recommend founders predict out how their role is going to change in 6 to 12 months, and work towards evolving now. What skills do you need to build by then? Who should you talk to to prepare? How can you efficiently make the transition? Evolving along with your company’s needs is critical to you and your company continuing to grow.

As you know, “conversion” means to convert a visit into a sale. In your experience what are the best strategies a business should use to increase conversion rates?

David: While specific conversion optimization tactics are unique to every business, investing in data and testing are universally important to increasing conversion rates. If you are not collecting data, and rapidly deploying A/B tests, there is no way to methodically increase your conversion rates.

Once you have the right data and testing systems set-up, it is important to collect testing ideas from teammates and customers, so that you can prioritize the most high-impact ideas.

Of course, the main way to increase conversion rates is to create a trusted and beloved brand. Can you share a few ways that a business can earn a reputation as a trusted and beloved brand?

David: Building a beloved brand is reliant upon solving problems for customers. The strongest brand relationships are when you can fully rely on a company to help you with whatever brings you to them time and time again.

Earlier, you mentioned “purpose-driven” businesses. The best and most beloved brands are truly purpose-driven, and effectively communicate that to their customers. Brand marketing is very important, but it should be the last 10% of your efforts. 90% of building a beloved brand is building a great product, or delivering a great service — it is ultimately fulfilling your mission for the customers.

Great customer service and great customer experience are essential to build a beloved brand and essential to be successful in general. In your experience what are a few of the most important things a business leader should know in order to create a Wow! Customer Experience?

David: This is a great follow-up to the question on branding because customer experience and branding are so interdependent. Building a wow! customer experience is a process reliant on identifying gaps, and scaling solutions to as many customers as possible.

Talking to customers, analyzing product data, and consulting with industry experts, are all critical avenues to identify how to improve your product. It’s important to seek out critical feedback and not just talk to fans who are likely to applaud you.

The key differentiator for those creating wow! customer experiences are not just collecting these insights, but being able to translate them into scalable applications. If you can establish a process of capturing insights, building them into a product, and scaling them to your customer base, you will constantly surprise and delight your customers by always improving.

What are your thoughts about how a company should be engaged on Social Media? For example, the advisory firm EisnerAmper conducted 6 yearly surveys of United States corporate boards, and directors reported that one of their most pressing concerns was reputational risk as a result of social media. Do you share this concern? We’d love to hear your thoughts about this.

Phil: Social media can be a mirror, reflecting back the values and customer experience a company has. Companies which don’t have strong values or don’t have a great customer experience should be concerned with reputational risk.

The fix isn’t to be scared of social media, it’s to improve your approach so you are serving customers better. At the end of the day every company has this challenge and the companies who adapt better will thrive long term.

What are the most common mistakes you have seen CEOs & founders make when they start a business? What can be done to avoid those errors?

Phil: The most common mistake we have seen is losing focus. There are a lot of activities and tasks required to start and grow a business. First-time founders in particular can get overwhelmed quickly by the sheer number of items coming at them. Add on the usual amount of firefighting, short-term issues, and before they know it they are only spending 10% of their time solving customers problems. If you are only spending 10% of your time on customer problems, there is going to be a competitor out there who can serve your customers better.

This can be mostly avoided through disciplined planning and constant prioritization. It’s also important to surround yourself with a strong support system of advisors or mentors who have been here before. Many business building problems you will face have likely already been solved. The goal is to spend less time reinventing the wheel and more time solving the problems unique to your business.

Thank you for all of that. We are nearly done. You are a person of great influence. If you could start 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. 🙂

David: A movement for more people to start more bold companies! The best companies solve big problems. Startups and small businesses are the foundation of modern economies, and help build the future. If there were a movement which encouraged more entrepreneurship, it’s like a movement starting up tons of other movements — ultimately it is a flywheel that would bring the most amount of good to the most amount of people.

How can our readers further follow you online?

David: I’m on LinkedIn and also write on the wilburlabs.com blog.

Phil: I’m most active on Twitter and LinkedIn.

This was very inspiring. Thank you so much for the time you spent with this!


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