The Holly Hester-Reilly Hypothesis: Great Products Come When You’re Not Afraid of Failure

What is Product Science?

Listen to the inaugural episode of the Product Science Podcast to find out. We’re focused on helping startup founders, and product leaders build high-growth products, teams, and companies. We have real conversations with the people who have tried it and aren’t afraid to share the lessons they’ve learned (and the mistakes they’ve made) along the way. The Product Science Podcast is hosted by Holly Hester-Reilly, Founder and CEO of H2R Product Science.

In this episode, we’ll talk about Holly’s background, what evidence-based product science is all about, and what you as a listener (and hopefully a subscriber) can expect to get out of this podcast going forward.

Questions We Explore in This Episode

  1. What components make for a high-growth product? What do Holly and H2R Product Science mean when they say they teach the science of high-growth product development?
  2. How did Holly get into product management in the first place? How did her experience as a chemical engineering researcher at Columbia University launch her into the NYC tech industry? What did she learn from her time as a Senior Product Manager at MediaMath? How did evidence and research guide her work as a Group Product Owner at Shutterstock?
  3. What is the Product Science Podcast going to cover? What does continuous product discovery mean? Why is continuous interviewing the key to the best products and product development teams? How can we find the patterns that high-growth products across industries have in common?
  4. How can you be empowered as a product manager in your organization? How can you convince people in your company to make decisions using evidence instead of basing them on the highest-paid person’s opinion? Why is product management about more than just taking orders?
  5. What interviews are coming up next?

Quotes From the Episode

“Most great products had somebody with a passion, somebody with a vision, and somebody who was not afraid to keep trying.” – Holly Hester-Reilly

“The only way to get to something great is to try and not be afraid to fail.” – Holly Hester-Reilly

“At H2R Product Science, we teach the science of high growth product development. What do I mean by that? Well, what I mean is that there are repeatable aspects to what makes a high growth product, how you build a high growth product, what a high growth product team operates like, and I want to bring those principles out and share them with you all and help you all learn how to do it too.” – Holly Hester-Reilly

“Continuous product discovery is the practice of making a regular habit, a regular process, of testing your ideas, testing your assumptions, testing your products, testing the business value or the usability or the feasibility of the product that you’re trying to build.” – Holly Hester-Reilly

We Want to Hear From You

What stories do you have of product decisions—the good and the bad—from your organization? Tell us and tag Holly on your favorite social media platform for a chance to be featured in a future episode.



Holly Hester-Reilly: Hi, and welcome to The Product Science Podcast, where we’re helping startup founders and products leaders build high-growth products, teams, and companies through real conversations with people who have tried it and aren’t afraid to share lessons learned from their failures along the way. I’m your host, Holly Hester-Reilly, founder and CEO of H2R Product Science.

Holly Hester-Reilly: Hi, and welcome to The Product Science Podcast. I’m so excited to be starting this podcast; it’s something I’ve been thinking about for a long time, I can’t wait to share it with you, my wonderful listeners.

Holly Hester-Reilly: So, let me tell you a little bit about what The Product Science Podcast is and why I’m so excited. First, you might be wondering who I am. My name is Holly Hester-Reilly, and I am the founder and CEO of H2R Product Science. We are a product management training and consulting company based in New York City. We got started in January of 2017. At H2R Product Science, we teach the science of high growth product development. What do I mean by that? Well, what I mean is that there are repeatable aspects to what makes a high growth product, how you build a high growth product, what a high growth product team operates like, and I want to bring those principles out and share them with you all and help you all learn how to do it too.

Holly Hester-Reilly: How did I get here? Well, the reason why I am saying that is because I’ve been in the New York City tech industry for over a decade, and before that, I was a Columbia University research scientist, doing academic research into chemical engineering, specifically targeted drug delivery, and I loved doing lab science and planning experiments and doing landscape research to understand what had already been learned that I could build off of. But I didn’t love some of the other elements of the research scientist life, and I found that the New York City tech industry was very young but exciting at the time, and I ended up making the switch over to the New York City tech industry. I’ve been in it for over a decade now. The first five years were in early-stage startups where the team was less than ten people. And the last five years were high growth startups. I went through some really incredible growth stories.

Holly Hester-Reilly: The first one was MediaMath, which is now a unicorn. MediaMath is an ad-tech company, and, it’s based here in New York City, led by Joe Zawadzki who is a great visionary for actually what I think of as sort of evidence-based advertising. When I joined MediaMath, the,re were 140 people there, and I was there through this incredible growth period. In just three years we went to 800 people. I was a senior product manager there, working on a new interface for their flagship product, which was a platform in a complex ecosystem, running ad technology. I saw so many things in those years, and I learned so much from so many great people who worked at MediaMath during that time.

Holly Hester-Reilly: After that, I went to Shutterstock, which had already iPod, was one of Silicon Valley’s earliest success stories for tech IPOs with their founder Jon Oringer having become Silicon Valley’s first billionaire or founder billionaire. And when I went there, I got to really make a big impact. I started off analyzing a struggling business unit called Skill Feed, and making the case with evidence that we should just shut it down, which was not easy but was a transformational experience for me and a great thing for the company because we were able to redirect those resources.

Holly Hester-Reilly: From there, I led the launch of Shutterstock Editor, from prototype to successful public beta, and that was in just three months. We got praise from our target users who loved that it saved them time and it made their lives easier. From there, we built out a product strategy and a road map and a resource plan for how to scale the team three times the number of resources on it. By the end of Shutterstock Editor’s first year, the team was continually delivering valuable improvements, and, the product users had grown 10X from its first month. So, that was an incredible opportunity and incredible experience for me to be the product leader, working on that in the related workflows.

Holly Hester-Reilly: After that, I did a couple of other projects at Shutterstock, and then I left and founded H2R Product Science. In total, I’ve worked on over a dozen new product launches, and I’ve worked with early-stage startups as clients, I’ve worked with growing companies, I’ve worked with enterprises trying to be more innovative or increase the product capacity. At the end of the day, what I most care about is that the people I work with are smart, they are ambitious, they are curious, and they want to know what works and why does it work and how can they apply it in their environment and their context. They’re willing to try things, and they’re willing to have those things fail, but along the way, they know that they’ll grow, and some of the things will work, and then they’ll keep moving forward, and they’ll learn more, and they’ll do more and they’ll grow more. I’m super excited to share these learnings with all of you.

Holly Hester-Reilly: Okay. So, why am I excited about this podcast? Well, one of the main things that I teach is continuous product discovery. Continuous product discovery is the practice of making a regular habit, a regular process, of testing your ideas, testing your assumptions, testing your products, testing the business value or the usability or the feasibility of the product that you’re trying to build. In the process of doing continuous product discovery, one of the things that I teach is doing continuous interviewing. I think the best product teams have a regular pipeline of interviews, and they’re constantly testing whatever the biggest, riskiest things going on with them in a given week, a given sprint, they’re testing those things with actual customers with their target market.

Holly Hester-Reilly: So, I’ve been doing that for years, I did that when I was at Shutterstock, launching Shutterstock Editor, and I did that when I was at MediaMath, and we were building a new user interface for the platform. I think it is one of the lowest effort, most valuable things to do. So, when I decided that I was going to start my own company, of course, I started doing that for my company.

Holly Hester-Reilly: So, in my first year of business, I talked to probably about 100 people about the state of product management and what they were trying to do to build high growth products, and learned about different organization structures and different challenges they faced and started to really see some patterns about how things worked across different sized companies, different stages of companies, different industries, different types of tech stacks, different skill levels in the talent of the organization. I just felt like I was learning so much, and I loved it. But it felt like such a shame, why would I keep that all to myself, shouldn’t everybody learn all of these things? I’m really driven by helping other people learn how to build a great product, and I want to scale this knowledge and scale the capability of building good products that make a difference for real customers, that make a difference for real people, whether it’s helping somebody with a B2C product, maybe just make their daily life a little easier at home, manage some of the chaos a little better, or whether it’s a B2B product and it’s helping people in the workforce get their jobs done better, make a bigger impact.

Holly Hester-Reilly: I want more product managers to feel excited about what they’re doing. I want more product leaders and more startups founders to feel like they have the tools and the toolkit to consistently work towards their vision and feel comfortable with the failure that comes all along the way. Because the only way to get to something great is to try and not be afraid to fail, because you will learn from every misstep and then you’ll get stronger, and then you can try again in a different way. Sure, there are some people out there that just luck into something amazing and it takes the world by storm and their story has few failures in it, and oh my God, now they’re millionaires or billionaires. But, the secret is that most great products, what they had was somebody with a passion, somebody with a vision, and someone who was not afraid to keep trying and to learn from the things that they tried and what worked and what didn’t, and to have that growth mindset.

Holly Hester-Reilly: So, I want to help the startup founders of today and tomorrow, and the product leaders of today and tomorrow, I want to help them have that growth mindset, I want to help them learn from the stories of people who have been there before, and I want to help them feel empowered within their organizations to make a difference, to fight for the right thing because so many product managers that I talk to tell me, “Well, Holly, I didn’t understand why my boss asked me to build this feature or this thing. And I thought that the strategy that we’re following didn’t make sense because I had some counter-evidence to it but nobody would listen when I tried to tell them.” I know far too many product managers who have decided that it wasn’t the right career for them or lost faith that they would be successful in this area, not because they didn’t understand how to build a good product, but because they didn’t know how to convince the other people in their organization. They didn’t have the confidence to set forth their strategy with compelling evidence, and they couldn’t change the minds around them. Their organizations fell back to leading by the highest paid person’s opinion, and they would be demoralized and stop trying or think that product management is just about taking orders and not developing a strategy, developing a product towards that mission, testing and iterating until you get there.

Holly Hester-Reilly: I want them to know that there are ways around that. If you’re facing that, we can work on it, and I want to share stories with you of people who’ve done it, and I can share my story as well. Just know that people like me are out here, and we do coaching and training and just put content into the world to try and help others, especially those who are inspired to make a difference and to build something good in the world.

Holly Hester-Reilly: I had all these conversations already and they were so transformative and exciting, and I would go and tell the people that I saw the next day or people that I saw online and I just wanted to make this more accessible and public. So, after some handwork and some good luck and some good fortune, I’m excited to be launching this podcast now, and I hope that you find it as valuable as I have found these conversations. My goal for The Product Science Podcast is for us to have people who are still rising up here from people who’ve been there but feel like they’re eavesdropping on a nice private conversation.

Holly Hester-Reilly: So, help me, hold me to it. The podcast can only get better with your feedback. I really want everybody to share their thoughts, their questions to tweet and post on LinkedIn and social media what questions they have and how they’ve tried to use this, and did any of these stories help them in their organization because I think these tales from the trenches can be really powerful.

Holly Hester-Reilly: I think you’re going to be pretty excited about our guests. I’ve already interviewed Marty Cagan the founder of the Silicon Valley Product Group, Barry O’Reilly from author of Lean Enterprise and recently number one bestselling business management book Unlearn. I’ve interviewed a couple of startup founders, Michelle [Feaster 00:11:59] and Patrick Campbell who are doing some pretty incredible things with their companies, and some product leaders who are out there making an impact with companies every day. I can’t wait to record even more and share even more of these stories.

Holly Hester-Reilly: Let’s see, is there anything else you should know about this show? Well, I have been inspired by Christopher Lochhead’s Legends and Losers, which is now renamed to Follow Your Different. The thing about it that I love is that it is a dialogue show instead of a standard interview. So, the length of the episodes can vary because he’s trying to have a real, natural conversation and it’s however long it lasts. So, that’s going to be true for mine as well. I think most often, the episodes will be probably around 45 minutes, but if there’s a conversation that’s just really deep, I’m not going to cut it short just because of that. I want you to be able to learn as much as possible and, hey, if I’m having fun with the conversation then hopefully you’ll have fun listening.

Holly Hester-Reilly: We’re going to do seasons. So, the first season will probably be about a dozen episodes or so, and then we’ll take a little break and gather feedback and test and iterate. Then, if everything’s going well, we’ll come out with another season after that. Episodes will release once a week, and you’ll always be able to find them on your favorite subscription services or at We’ll be super excited if you’ll share and let us know what you’re thinking and how you like the show.

Holly Hester-Reilly: Thank you so much for listening. I’m super excited to begin this journey with you, and let’s build some awesome products.

Holly Hester-Reilly: Enjoying this episode? Don’t forget to subscribe so that you don’t miss next week’s episode. I also encourage you to visit us at to sign up for more information and resources from me and our guests. If you loved the show, a rating and review would be greatly appreciated. Thank you.