The happiness and pain of product management | Noam Lovinsky (Grammarly, FB, Thumbtack, YT)

Summary

In this insightful podcast interview, Noam Lovinsky, the Chief Product Officer at Grammarly, shares his diverse career journey and valuable lessons learned from working with major tech companies like YouTube, Facebook, and Thumbtack. Lovinsky reflects on his experiences, from turning around YouTube's initial financial struggles to building Facebook's New Product Experimentation team. He emphasizes the importance of aligning with a company's broader strategy, the value of resilience in product development, and the significance of having a diverse set of skills within a leadership team. Lovinsky also highlights the unique success factors of Grammarly, a B2C subscription business that has managed to thrive and grow sustainably. His advice for career success centers around pursuing opportunities for growth and learning, even when they come with challenges, and focusing on work that genuinely energizes and fulfills you.

Takeaways

• 🎯 Prioritizing what's best for the business over personal goals can lead to better outcomes and is a sign of a healthy organization.
• 💪 Advocating for team well-being over personal career advancement can be a difficult but rewarding decision in the long run.
• 🚀 Building a startup within a large company requires a different incentive system and operational model to avoid stifling innovation.
• 🤝 Collaboration across different departments at the leadership level is crucial for tackling challenges and driving growth.
• 📈 Diversifying growth channels is essential for long-term sustainability, as reliance on a single channel can be risky.
• 🛠️ Scrappy, bootstrapped beginnings can instill a culture of resourcefulness and profitability that lasts as a company grows.
• 🧩 Finding a balance between new challenges and areas of expertise is key to personal and professional growth without overwhelming stress.
• 🤔 Reflecting on how a potential disruptor would approach your business can provide insights for innovation and improvement.
• 🌟 A strong product that delivers immediate value with minimal effort can drive user satisfaction and retention.
• 🔄 Embracing struggle as a means for growth and development can lead to stronger bonds and better outcomes.
• ⚖️ Having a solid foundation in a few key areas while stretching into new ones can maintain balance during periods of intense learning.

Q & A

What was the initial challenge when Noam Lovinsky joined YouTube?

When Noam joined YouTube, the platform was losing a significant amount of money, and there were internal considerations at Google about whether to sell YouTube.

How did Noam Lovinsky's role evolve at YouTube?

Noam started by rebuilding a product from a company he founded, which was acquired by YouTube. He then transitioned to leading the creator focus area at YouTube, working alongside Hunter Walk and Shishir Mehrotra.

What was a significant learning for Noam Lovinsky during his time at Thumbtack?

Noam learned the importance of not relying on a single channel for growth, as Thumbtack had done with SEO. He also realized that growth can mask underlying problems within a business.

How did Noam Lovinsky approach the challenge of rebuilding the growth engine at Thumbtack?

Noam focused on diversifying growth channels, rebuilding the customer experience to reduce friction, and changing the monetization model to provide instant quotes for services.

What was Noam Lovinsky's role in creating Facebook's New Product Experimentation (NPE) team?

Noam was part of the early team that helped build NPE, with the goal of incubating new product ideas within Facebook, protected from the larger organization.

What was a key takeaway from Noam Lovinsky's experience at Facebook regarding incubating new products?

Noam emphasized the importance of having the right incentive system and allowing for experimentation in a way that doesn't scale, which is crucial for discovering new products in a large organization.

What advice does Noam Lovinsky give to product managers for career success?

Noam advises product managers to seek out roles and opportunities that will lead to significant growth and learning, even if they involve pain and challenges, as these experiences can be highly rewarding in the long term.

How does Noam Lovinsky describe the user experience of Grammarly?

Noam describes Grammarly as a product that requires minimal configuration and works seamlessly across all applications to provide immediate assistance to users, requiring very little effort to extract value.

What is Noam Lovinsky's view on the importance of finding work that energizes you?

Noam believes that it's crucial to focus on work that gives you energy and brings you joy, as life is short and there's no reason to spend time on things that don't fulfill you.

What is the significance of the Grammarly team in Ukraine, according to Noam Lovinsky?

The Ukraine-based team at Grammarly is highly dedicated and has contributed significantly to the company's success. Despite challenging circumstances, they continue to operate effectively and take pride in their work.

What does Noam Lovinsky recommend for someone considering a new job or career move?

Noam recommends that individuals should prioritize positions that will cause growth and learning, even if they are challenging, as these experiences can lead to significant personal and professional development.

What is Noam Lovinsky's approach to interviewing candidates?

Noam prefers interview questions that allow him to work through a product problem with the candidate, believing that this approach provides a better understanding of the candidate's capabilities and thought process.

Outlines

00:00

😀 Noam Lovinsky's Diverse Tech Experiences

Noam Lovinsky, the guest for the podcast, has had a varied career, working at companies like YouTube, Facebook, and Thumbtack, and is currently the Chief Product Officer at Grammarly. His experiences range from turning around struggling projects to incubating new ideas within large organizations. Lovinsky's approach to product management and his insights into when to kill a project or seek a change within a company are discussed, along with his advice on career growth and finding work that challenges and stretches one's abilities.

05:01

🤔 Authenticity in Career Growth and Networking

Noam discusses the importance of authenticity in one's career, emphasizing that he prefers to build relationships through work rather than networking. He also addresses the question of whether one should invest time in online presence for career advancement, suggesting that it's more important to focus on what comes naturally and is authentic to the individual. His advice is to focus on what you enjoy and excel at, rather than what you think might lead to success.

10:09

🚀 Lessons from YouTube's Growth and Strategic Decisions

Noam shares his experiences from his time at YouTube, where he made strategic decisions that influenced the company's direction. He talks about advocating for what's best for the team and organization, even if it means personal risk. His journey from working on a rebuilt product to leading a focus area at YouTube highlights the importance of honesty and openness in prioritizing work and the benefits of a healthy organizational culture.

15:16

🔄 Prioritization and the Importance of Broad Views

The discussion emphasizes the importance of aligning one's work with the company's broader strategy and goals. Noam talks about his approach to prioritization and decision-making, suggesting that product managers should consider what's best for the business as a whole. He also shares insights on how to handle situations where projects aren't going well and the decision to move on from them.

20:18

📈 Reversing Fortunes at Thumbtack and Growth Lessons

Noam recounts his time at Thumbtack, where the company experienced significant growth, followed by a downturn due to changes in Google's SEO. He discusses the lessons learned from this experience, including the importance of not relying on a single channel for growth and the value of going through tough times as a business. His account of turning around Thumbtack's growth engine provides insights into resilience and strategic shifts.

25:23

🌱 Building a Sustainable Business and the Role of Leadership

Noam reflects on the importance of involving the entire leadership team in product strategy, especially during challenging times. He emphasizes that everyone, regardless of their role, should have a part to play in the company's strategic direction. His experiences have taught him the value of collective effort and the need for all leaders to contribute to solving problems.

30:29

🛠️ The New Product Experimentation Team at Facebook

Noam talks about his role in creating Facebook's New Product Experimentation team, which aimed to incubate new startups within the larger company. He discusses the challenges and benefits of this approach, including the difficulty of operating at a small scale within a large organization and the importance of creating an environment that allows for experimentation and learning.

35:29

🎯 Advice for Creating a Startup Within a Larger Organization

Drawing from his experience at Facebook, Noam offers advice for those looking to create a startup-like environment within an established company. He stresses the importance of having the right incentive system and allowing for independent infrastructure choices to foster innovation. He also highlights the need to compete with the appeal of starting one's own company to attract and retain talent.

40:29

📚 The Success and Strategy of Grammarly

Noam provides insights into the success of Grammarly, a leading B2C subscription business. He discusses the company's focus on user experience and the seamless integration of AI technology. He also touches on the company's origins, its profitability from the start, and the strategic decision to operate under the radar. Noam shares his perspective on the company's future and its potential in the evolving tech landscape.

45:36

💼 Career Advice and Embracing Struggle

Noam shares his philosophy on career development, emphasizing the importance of seeking growth and learning opportunities even if they come with challenges and discomfort. He advises on finding a balance where one can rely on their strengths while also stretching into new areas. Noam also encourages focusing on work that aligns with one's passions and brings energy, as life is short and there's no reason to spend time on unfulfilling endeavors.

Keywords

💡Product Management

Product Management is a function within an organization that focuses on guiding every stage of a product's lifecycle, from idea to market launch and ongoing improvement. In the script, Noam Lovinsky discusses his experiences in product management at various companies, emphasizing the importance of aligning projects with company strategy and advocating for decisions that benefit the team and organization as a whole.

💡YouTube

YouTube is a video-sharing platform that Noam Lovinsky joined during a challenging financial period for the company. His work at YouTube involved rebuilding a product on Google infrastructure and later leading the creator product experience. The script highlights YouTube's growth from losing money to a significant business success, with a current valuation of $200 billion.

💡Thumbtack

Thumbtack is a platform that connects customers with professionals for various services. Noam Lovinsky helped the company reignite growth after a downturn caused by changes in Google's SEO. The script describes a turnaround story where the company faced negative growth and had to rebuild its product and monetization model to achieve a successful 'smile graph' of growth.

💡Facebook

Facebook is a social media platform where Noam Lovinsky created the New Product Experimentation (NPE) team. The team aimed to incubate new ideas within the larger Facebook organization. The script discusses the challenges and learnings from this experience, including the importance of having the right incentive systems and the ability to work on small-scale projects that could potentially scale up.

💡Grammarly

Grammarly is an AI-powered writing assistant that provides grammar, spell checking, and other writing aids. Noam Lovinsky describes it as a successful B2C subscription business that has been profitable from the start. The script highlights the product's user-friendly approach and its ability to integrate seamlessly into users' workflows as key to its success.

💡Incentive Systems

Incentive Systems are mechanisms used within an organization to motivate employees to achieve specific goals. Noam discusses the importance of having the right incentive system in place, especially when creating a startup within a larger company. The script points out that misaligned incentives can lead to adverse selection and hinder the success of innovative initiatives.

💡Growth Channels

Growth Channels refer to the various methods a company uses to reach new customers and expand its market. In the script, Noam talks about the risks of relying on a single growth channel, as seen with Thumbtack's initial dependence on SEO. He emphasizes the importance of diversifying growth channels to ensure the company's long-term sustainability.

💡Strategic Thinking

Strategic Thinking involves the ability to think about the future direction of a business and make decisions that align with long-term goals. Noam Lovinsky's experiences at YouTube, Facebook, and Thumbtack exemplify the need for strategic thinking, where he had to make tough decisions that were in the best interest of the business, even if they were personally challenging.

💡Leadership

Leadership is the act of guiding a group of people towards achieving a common goal. The script discusses Noam's leadership experiences, including his decision to report to another leader at YouTube to improve his work and the importance of having every member of the leadership team engaged in product strategy during challenging times at Thumbtack.

💡Innovation

Innovation is the process of introducing new ideas, methods, or products. Noam's work with the New Product Experimentation team at Facebook and his role in rebuilding Thumbtack's growth model exemplify the pursuit of innovation within established companies. The script highlights innovation as a key driver for business transformation and growth.

💡Career Growth

Career Growth refers to the process of progressing in one's career, taking on new challenges, and achieving higher levels of responsibility. Noam advises focusing on positions that will cause personal growth and learning, even if they come with pain and discomfort. The script emphasizes that career growth should be aligned with personal passions and strengths for long-term success and fulfillment.

Highlights

Noam Lovinsky discusses his diverse career journey, including his experiences at YouTube, Facebook, Thumbtack, and Grammarly.

Provides insights on when it's appropriate to terminate a project within a company and the importance of aligning with the company's broader strategy.

Shares lessons learned from YouTube's transition from losing money to a $200 billion valuation.

Talks about the challenges and strategies involved in turning around Thumbtack's growth after a downturn in SEO.

Explains the concept of the New Product Experimentation team at Facebook and its role in incubating new ideas within the larger organization.

Advises on the importance of finding work that stretches you and contributes to career advancement.

Discusses the creation of space for innovation within large companies and the unique set of experiences that Noam brings to his role at Grammarly.

Noam reflects on his low-profile approach to social media and online presence, emphasizing the importance of authenticity in career building.

Provides advice for product managers on focusing on what's best for the business rather than just immediate user satisfaction or team goals.

Highlights the importance of stamina and resilience in product development, especially during periods of uncertainty or difficulty.

Explains how Grammarly's success is attributed to its user-friendly approach and the product's ability to seamlessly integrate into users' workflows.

Noam emphasizes the scrappy and profitable beginnings of Grammarly, which influenced its culture of careful growth and investment.

Discusses the need for diversification and future growth strategies as Grammarly transitions from a startup to a larger entity.

Shares personal advice on career development, encouraging individuals to seek out roles that will foster growth and learning, even if they are challenging.

Noam recommends the book 'Build' by his wife and Tony Fidel, highlighting the value of persistence and the energy derived from work that excites you.

Provides insights into the importance of maintaining a balance between new challenges and leveraging existing strengths in a career.

Talks about the impact of the Ukraine conflict on the Grammarly team and their resilience in continuing to operate successfully.

Transcripts

You've worked at so many great companies. At  YouTube, when you joined, my understanding  

is YouTube was losing a lot of money. There were many times where Google leadership  

reconsidered the acquisition and, "Should we  sell YouTube?" if you can believe it or not.  

At Thumbtack, it looks like you went  from 1 to -1 and then back to 1.  

I remember in a board meeting, the new  model really started to show legs and  

one of the board members, Brian Schreier  at Sequoia, said it was the prettiest  

smile graph that he had ever seen. When you were at Facebook, you built what  

is called the New Product Experimentation team  trying to create a startup within a startup.  

You're thinking on a different time horizon.  If you're a large organization and you do  

some performance management process twice  a year and you're 0 to 1 incubator, you've  

already killed it. It's the wrong incentive. As the chief product officer of Grammarly, I'm  

curious what word you most often misspelled? The.  

You do T-E-H? T-E-H. Yeah, exactly. Yeah, yeah, yeah.  

Oh man. Today my guest is Noam Lovinsky. Noam  

is currently chief product officer at Grammarly.  Previously, he was an early PM at YouTube where  

he spent five years leading the creator product  experience and then the broader YouTube consumer  

product experience. He then went on to take on  the chief product officer role at Thumbtack,  

which involved helping the company reignite  growth after a downturn caused by some changes  

Google made in SEO. He then went on to Facebook  where he created the New Product Experimentation  

team whose charter was to incubate big new  ideas protected from the larger Facebook org.  

Noam has such a unique set of experiences taking  products from 0 to 1, from -1 to 1, from 1 to 100,  

and even starting his own companies. He's never  really been on a podcast before and he rarely ever  

tweets or post anything online, which we actually  talk about. In our conversation, we walk through  

the lessons that he's learned through his amazing  career at YouTube, Facebook, Thumbtack, and at  

Grammarly. We talk about when it makes sense to  kill your project at a company, when it makes  

sense to ask to be layered at a company, why you  should be keeping a nose out for which products  

matter most at a business and to find those  products, why you need to diversify your growth  

channels at your business, why you should be  finding work that is going to most stretch you to  

help you advance in your career, a bunch of advice  for creating space for innovation within a large  

company and so much more. Noam is such a gem and  I'm really excited to share his wisdom with you.  

If you enjoy this podcast, don't forget to  subscribe and follow this podcast in your favorite  

podcasting app or YouTube. It's the best way to  avoid missing feature episodes and it helps the  

podcast tremendously. With that, I bring you Noam  Lovinsky after a short word from our sponsors.  

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vanta.com/lenny. That's V-A-N-T-A.com/lenny. Noam, thank you so much for being here  

and welcome to the podcast. Thanks for having me, Lenny.  

It's absolutely my pleasure. I've heard so many  great things about you from so many people. I  

think you're friends with a lot of guests that  have been on this podcast. Something that I find  

really interesting about you and really respect  about you is that you've worked at so many great  

companies and you've done so many big things in  your career, but you barely ever tweet. You don't  

have a newsletter. I don't see many things  on LinkedIn. I don't think you've even been  

on a podcast before. I think the only evidence I  can find that you exist is you have this YouTube  

channel that's just like you go-karting and  kids and people wishing you a happy birthday.  

Oh gosh, I should go monitor  that. I forgot about that.  

You might want to go find it now. Yeah, yeah, yeah that's funny. Yeah,  

it's funny. I think about that a lot, like am I  doing something wrong? Should I be putting more  

effort in that? I mean, it's funny that you  mentioned newsletter. I spend a lot of time  

with the Substack team's. I've been a very active  advisor there. The team is fantastic by the way.  

And I think about it. Am I doing something wrong  in my career by not doing that? But just to be  

honest, it doesn't come authentically to me. It  doesn't come naturally to me. I get really focused  

on the thing that I'm working on and get really  deep in the thing that I am working on and I have  

a hard time kind of multitasking a lot outside  of that to be totally honest. The way that I  

kind of get to know the industry and other teams  or whatnot is just through working with people.  

I'm not a very big networker. I'm not  saying that there's anything wrong with  

that. I wish I were better at that. I get  to know people by doing work with them,  

by helping them. And it doesn't necessarily  scale in the same way that Twitter does,  

but it's served me well so far and it's more kind  of authentic and it's what comes more natural to  

me. And so that's how I do it. So I'm doing a lot  of coffees. I'm meeting people that way. I'm not  

doing a lot of tweeting or writing of newsletters.  Maybe one day, but that's not me today.  

So I think this is an awesome example of you can  be incredibly successful as a product manager  

and as anyone in tech not investing time posting  online. I am going to incriminate myself here, but  

I feel like the advice I always share with people  is the best people are not spending time tweeting  

and talking online and sharing on LinkedIn.  They're just doing the work. They don't have time  

for that sort of thing. And I think you're a great  example of that. Is there anything along those  

lines that you share with folks that are just  like, "Hey, should I be investing time here?"  

I think everyone can chart their own path and has  a way that is sort of authentic to them and leans  

on their strengths. What I often coach people is,  do what you like. You're generally going to be a  

lot better at the things that really fill you  up that really get you excited. Life is short.  

There's so many things to be doing out there.  We're so lucky. The number of interesting waves  

of technology that I've experienced, it just makes  me feel like it's going to keep happening for a  

long time. We're very fortunate to be born in the  time that we are and have the opportunities that  

we are. So why spend your time doing something  that doesn't feel good because you think that it  

might lead to some success, where if you lean on  what's authentic to you and what makes you happy,  

chances are you're going to be one of  the best people at those things?  

I love that advice. And I think it's so important.  I think there's a lot of pressure on people too.  

"I need to do this, I need to do that." Totally.  

"I need to tweet, I need to share content to be  successful." This comes up a lot in this podcast,  

that the more you could just stick close to  what gives you energy and what you enjoy doing,  

oftentimes that leads to things you  wouldn't expect in a lot of success.  

Speaking of that, looking at your career arc,  I noticed a really interesting pattern and a  

really diverse set of experiences. So just kind of  talking through places you've been. At Facebook,  

you worked on 0 to 1 stuff. At YouTube, the  way I see it as you almost went from -1 to 1.  

At Thumbtack, it looks like you went from 1 to -1  and then back to 1. So it's like a really unique  

turnaround story. And then with Grammarly it feels  like it's like, I don't know, 1 or I don't know,  

5 to 100, or wherever you end up taking it. So I  thought it'd be fun to talk through each of these  

experiences because they're such unique approaches  or such unique experiences and see what lessons  

and wisdom we can extract from your journey. That sounds great. Yeah.  

Okay, sweet. So I'm thinking reverse  chronologically, we start with YouTube,  

which the way I see it is it's kind of -1 to 1.  When you join, my understanding is YouTube was  

losing a lot of money. When you left, they were  not losing money. And I was actually just looking,  

they're valued apparently at $200 billion  today, YouTube as a business. I know you  

haven't been there for a while, but great work.  What lessons did you take away from that journey?  

What stories come to mind from that part of  your career that might be helpful to people?  

Maybe first to start looking with why hop around  these experiences. I always tell people I feel  

like I'm an IC trapped in a manager's body  sometimes. Fundamentally, I like to build,  

that's why I do this. I like to make things. And  so sometimes the more fun way to make things is  

to start something and sometimes the better way  to make things in the situation that I'm in is  

to try to support teams and lead through teams. And so I joined YouTube through an acquisition  

of a company I started. In the beginning,  what I was doing there is just rebuilding  

that product on Google infrastructure and for  YouTube customers. And maybe the first lesson  

was actually to look around at what the  rest of the team was doing and be really  

honest and open about the relative priority  of the thing that you're working on even if  

it might lead to your project getting canceled. So one of the things that I remember doing really  

on is actually talking to the leadership team and  being like, "I don't think we should be putting 50  

engineers on this project. Looking at the rest of  the roadmap and the rest of the priorities, excuse  

me, I think this team would likely be better  served elsewhere." Even though that was likely  

negotiating my way out of a job in month three,  I don't know, I kind of felt like that was the  

right thing for the team and for the business. And then that started a very interesting journey  

because from there, basically the leadership was  like, "You're right. We're going to wind that down  

and build some of those features into the existing  product. And now you, you come and lead this focus  

area, we're calling the creator focus area." So  I went from basically rebuilding the product that  

our startup had built to leading one of the three  focus areas at YouTube. There was the viewer team,  

the creator team, and the advertiser team.  And Hunter Walk, who's amazing, was leading  

the viewer team. And Shishir Mehrotra, who's also  very amazing, was leading the advertising team.  

What an alumni community. There was me. I was sort of  

like 29-year-old startupy guy working with these  guys who were awesome. And YouTube in general,  

and continues to be, an incredible team. And  so I think that was a first really good lesson.  

That in the right organizations, even in  large organizations, advocate for what's  

best for the team, advocate for what's best for  the organization even if that means that it puts  

you at a particular difficult moment. If it is a  healthy team that rewards those sorts of decisions  

and actions, good things will happen. If it's  not, that's good to know too. That's good to know  

early. So that's one thing that comes to mind. Maybe one other I would say atypical career choice  

that I made shortly thereafter is then when I was  put in that role, I really struggled in that role.  

I was reporting to the CEO at the time, a guy  named Salar Kamangar, who's also awesome, Google's  

6th employee and just learned a ton from him, like  an incredible strategic thinker. But he was asking  

me questions that I felt like they were from a  different planet. I was like, I didn't know what  

they meant and he just thought in a different way,  a different level or different scale and that's  

still something that I was learning. Eventually  I figured it out, but I was really struggling in  

that moment. I had a really good relationship  with both Hunter and Shishir and they really  

helped me through that. And eventually, I went to  Salar and said, "Hey, I think I should actually  

report to Hunter. I think this would work better  if we kind of combined the organizations this way  

and then we divided and conquered this way." And again, very atypical, no one has ever come  

to me in my career and said, "I would like you to  layer me in this other person." But in that moment  

I was just like, "This is how I will do better  work. This is how I will get better support.  

I will be happier and more productive and it'll  be better for the team." And you know what? For  

me anyway, I was right. We made that change.  Hunter was a fantastic manager and support at  

YouTube. I learned a ton, grew a lot. And then  eventually when he moved on, Shishir took over  

the organization and then I moved into the viewer  part of the organization, which is where I spent  

the rest of my time there, which was leading  and supporting the viewer PM team at YouTube.  

These stories are amazing. It connects to your  point that you're kind of an, I see, an inner  

child I see, where you keep trying to kill your  career by accident. Like, "Now, let's kill this  

project I'm working on. I'm going to demote  myself a little bit." But clearly it's worked  

out. Is there anything that you saw that gave you  that confidence that, "This is actually going to  

be okay"? Because again, people don't normally  think this is how you get ahead in your career,  

is you kill your team and you layer yourself. Yeah, I mean I think having a broader view of the  

company strategy, having an instinct for  what we should be doing and why and how  

I might prioritize all of these investments  if I were given the opportunity to do that,  

I think internalizing that and understanding that  and then trying to align whatever is under your  

influence towards that overall goal is very  helpful and made me feel like, "I'm pretty  

confident this is going to be okay because it  will lead to better results for the organization  

given what we're trying to do. And so as long  as I'm trying to push decisions or actions that  

actually lead to better results, if it's a healthy  culture and organization, I should be okay."  

I think that the other thing is, just over the  years, I got extremely lucky. The first job that  

I got out of school was an incredible group of  people and it gave me a nose for talent. It gave  

me a nose for what great feels like and what  a high functioning team feels like. It's hard  

to know that without experiencing that. And so in  the moments, YouTube was also one of those teams,  

Grammarly is one of those teams, Thumbtack  was one of those teams. Being able to sniff  

that out when you're trying to choose the  next team is very important. But I think  

that's another thing that gave me confidence.  I learned these people well enough, Hunter,  

Shishir, et cetera, to have the instinct that  the right thing will happen, like this will  

be better for me and the broader team. Got it. So the key there is just you have to  

trust that the team around you is good enough,  that you're not going to be pushed off into a  

corner. I think you made a really profound point  here that a lot of people don't get about the job  

of a product leader and a product manager, that  a big part of your job is to think about what  

is best for the business and work backwards from  that. Not necessarily what's the best thing for  

the user is the highest priority, not necessarily  what's the best thing for my team and how do I hit  

the goals that I'm obsessed with. It's what is  going to be best for the business broadly and  

then make decisions there. Is there anything more  you can say there about just how powerful that is  

as a way of thinking about prioritization  and decisions as a product manager?  

Yeah, it's a great question. I mean, I think  ideally, things that are best for the customer,  

there's high overlap with that with things  that are best for the business, but not always,  

right? And I think figuring out some principles  that help guide those sorts of conflicts can  

be really, really helpful. At Thumbtack, we had  principles about which sides of the marketplace  

we wanted to serve in which order and when we  serve Thumbtack. So it was customers first,  

pros second, and then Thumbtack last. And that's  actually the first two... Saying Thumbtack last  

is the easy thing to say. Actually doing it in  action I think is a very different thing. But that  

first one of like, should we... Especially when  you're starting a marketplace, as you know well,  

Lenny, supply is so critical. Many marketplaces  live and die by the quality and liquidity and  

supply. And so why would you focus on customers  first and the Thumbtack perspective and supply  

are the pros, the people that you hire? Well, we always just felt that what the  

pros need from us is more customers. What the  pros need from us is high quality customers.  

And so if we really try to make a great customer  experience that attracts more customers, helps  

them find the right pros, provides the highest  quality customers, then that will therefore  

be better for the pros. And so that's how we  should prioritize. If we do those things right,  

then the business will benefit, right? And so  doing things like raising prices because we  

think it's good for the business, even though it  causes liquidity issues in the marketplace might  

be a little bit of a local maxima, locally  optimizing rather than globally optimizing.  

So I think sometimes in these sorts of questions,  trying to establish some set of guiding principles  

that help navigate some of these more ambiguous  or thorny questions can be really helpful.  

I want to circle back to this first point you  made, an experience you had convincing people  

that your first project shouldn't be something you  work on. How long do you stick with something that  

isn't going well and then decide, "Okay, let's  convince people this is something I should move  

on from," versus you don't want to give up on a  project quickly, you want to give it a shot?  

I mean, look, I don't know that it's a perfect  answer, but I think the reality is just that  

what kills most projects most early companies is  stamina. And I think that we all need to work on  

being more resilient about kind of like,  I remember at Thumbtack, Marco, the CEO,  

we used to say that it feels like we're running  uphill and chewing glass, and you're kind of like,  

"That's right, we want to do that. That's  good for us. Take our medicine." So you  

want to practice that sort of resiliency. But  ultimately, I think that what starts to happen  

is you start to lose the stamina and you're just  not bringing your best self to the situation.  

And so many of these things that are so high  ambiguity where you don't know exactly what  

to build or you don't know exactly, you're not  getting the signal you need or the feedback you  

need to be able to hone it in and know that you're  doing something well. They require just an ungodly  

level of faith and stamina. And so that's sort  of what I look to. When you see a team that is  

motivated, that is building something like they're  really excited about, I mean just the inertia, the  

quality, it's like a whole different game where  when you see a team that's sort of down and out  

and they've really been hitting their head against  the wall for a long time, sometimes they just need  

a change of scene, a change of pace, and they get  to a much better situation. So my honest answer  

is, yeah, it's the, when do you run out of steam  is usually the question. I think that happens  

usually like in the startup case, a lot of times  before you run out money or these other things.  

We've talked about Thumbtack a couple of  times now, so let's talk about that. I love  

this description of running a pill, chewing  glass. My understanding is when you joined,  

things were going well, and then things started  to go much less well, and then you helped turn  

things around. Talk about that part of your  journey and what you learned from that time.  

Yeah, sure. Again, really fantastic team and  really strong founders. That company was just on  

the bleeding edge of things like SEO and growing  by SEO. It was one of the best organizations  

that are driving growth through that channel.  But I think a thing that I learned really early,  

which Lenny with your background you probably know  as well, SEO is a sort of a live by the sword, die  

by the sword channel of growth. I think that one  channel growth company is always a no-no. And so  

that's a little bit of what we had at Thumbtack. So it was funny, because I remember when I joined  

and Marco and I had an agreement where it's  like, "Okay, I'm going to do my three months  

of onboarding, listening to our new leader  inheriting a team." I've always gotten advice  

that that's what you should do. And Marco being an  entrepreneur and a hard running founder is like,  

"Yeah, yeah, yeah. Sure, sure." And then a month  in, it's like, "All right, we got to run 2024  

planning. Go." Or not 2024, sorry, at the time it  was. And yeah, in the early days when I was there,  

Thumbtack was seeing triple digit growth. Then  we had a couple SEO hits that got us down to  

double-digit growth. And then not too long after  that, we were actually, for the first time in the  

company's history, seeing negative year-over-year  growth and Google was just really coming down on  

our category as we were, by the way, trying  to rebuild the whole product and change the  

monetization model and everything in between. So it was a really a tough moment of how much do  

we kind of spend to reinforce the old model while  we're sort of building the new model, kind of  

changing the engine while the plane is flying. I  think I remember in a board meeting, once we kind  

of turned that around and over time and also the  new model really started to show legs and really  

started to work, one of the board members, Brian  Schreier at Sequoia, said it was the prettiest  

smile graph that he had ever, ever seen. It  was obviously a really proud moment there.  

But I think that the thing that I took away  from that, which I tell PMs quite a bit,  

is growth masks all problems. You don't really  have a, I think, true understanding of what  

is working well and what is not working well  when you have incredible growth. YouTube was  

a great example of that. And at Thumbtac, it had  incredible growth for quite some time, but it was  

essentially burning through a lot of demand. It  was just dropping a lot of demand on the floor  

because there wasn't sufficient liquidity on  the supply side to really meet that demand. The  

team knew and was trying to work on that problem,  but it wasn't as urgent or high priority because  

you're having triple digit growth. What's  wrong? Everything's going great, right?  

And then the moment growth starts to slow or  certainly when growth starts to be negative,  

all of a sudden the tenor in the organization  really changes and you start looking at things  

very differently and trying to understand what's  actually going on. And so I think it's actually  

a very healthy thing for businesses to go  through as they turn into long-term sustainable  

businesses to have those sorts of moments,  because I think otherwise it's just really  

challenging to identify where the true issues  are. And I think as a PM, if you've only ever  

worked on things that grow and you've never felt  the other side of that and how to help turn that  

around with your team, I think you lose a lot  in your career if you don't experience that.  

I'm kind of naturally paranoid.  And especially as I manage growth,  

I often look at things and ask myself like,  "Okay, what do I do right now if it went  

negative? How would I prioritize things if it went  negative?" Having gone through that experience,  

I just look at things in a different way of  urgency. I look at things at different levels of  

priority having gone through that experience. With this Thumbtack story, I think it's rare  

that a business gets the smile graph that  you described, this prettiest smile graph  

that this board member has ever seen. I think  that is rarely the case. Usually, it doesn't  

come back up. Can you share what you did to help  Thumbtack turn things around? I know it's very  

particular to Thumbtack in the business, but just  anything there that would be useful to people?  

Sure. First of all, this is very much the team.  It's not just things that I did. So I mean,  

first was turning on multiple channels of  growth. Up until then, Thumbtack had tried  

and stopped paid channels, other organic channels  like referrals, all of the typical things. And so,  

we just went back to first principles on a  lot of that and also just kind of reformed a  

team around that and basically got an amazing  team together. One of them, Whitney Steele is  

running marketing at Descript now. Another one,  David Schein is running a product at HIMSS. But  

basically I went back to first principles on  some of those growth channels and experiment  

on our way to much, much better results. I think that one of the things that we were  

doing incorrectly at Thumbtack is Thumbtack  is actually a marketplace that is actually  

made up of thousands of marketplaces, right?  Like DJs in Philadelphia is one marketplace,  

DJs in Atlanta is another marketplace, contractors  in Sonoma is another marketplace. And then  

Thumbtack is obviously the container of all  of those marketplaces. I think we were just  

bifurcating our targeting and our growth efforts  a little too narrowly, assuming we had to grow in  

that way market by market rather than targeting  more broadly, providing the more aggregate data  

to Google and others, and then optimizing from  there. The fact that we already had really good  

showing in SEO and really good patriarch  and SEO helped to bolster things like SEM  

and then eventually Facebook as well. Those were kind of the growth levers,  

but the core issue with the Thumbtack product was  that it was just a very high friction customer  

experience that really left customers waiting.  So the way that Thumbtack worked basically was  

a customer would find them through a search query,  they would come in and they would answer a number  

of questions about the job they needed done,  and then Thumbtack would say, "Okay, great,  

we'll get back to you in 24 hours." And  this is a modern day experience, right?  

And then what Thumbtack would do is they would  take that job and they would federate it out  

to as many of the pros that might match the  criteria, and then the pros would pay to quote  

to show up as a potential provider for that job.  Now, I don't want to take anything away from that  

team because that worked phenomenally well for  a really long time. And actually it's a perfect  

case study in like, "|Just do the scrappy thing  that works to grow." And they did that very well,  

but the stage and size of the business when  I joined it had kind of outgrown that. And  

the team knew that. That's obviously a very high  friction experience. The idea that the customer,  

they're super excited, they want to hire  someone, and at that moment you'd be like, "Cool,  

talk to you soon," not the best experience. And the fact that you're asking your supply  

to put up money to even show up to customers in  the first place, well, what the customers want  

to see is the supply. Like, "Tell me who I can  hire." Also, a lot of friction on that side and  

also in some cases some unfair revenue on that  side because if folks are paying to be seen and  

maybe they're looked at, but there's not really  high intent, then they're not going to get the  

customers they want, they're going to be spending  revenue, they're not going to be getting revenue  

back. It turns into just a bad loop obviously. So the main thing we did is to rebuild that whole  

loop, change the monetization model, build a  system where essentially pros could provide  

instant quotes. Lenny, I'm sure from Airbnb, this  is very familiar, the move from request to book to  

instant booking. It was a very similar thing in a  different kind of category of service and supply  

obviously. But that shift and doing that shift  across those thousands of marketplaces and then  

finding the right friction point for monetization  and when and what to charge people for and all of  

that change, that is what really, at its core,  turned the growth engine around at Thumbtack.  

And it's just a real testament to those founders  that they believe that, saw that, and were willing  

to run a pill and chew glass to get to that  point. I don't know the details of the business  

anymore. And if I did, I wouldn't speak to it.  But from what I hear, things are going well,  

so I think that that served the company well. Yeah, as you were talking about that,  

that's exactly an experience Airbnb went  through. I actually led that effort at  

Airbnb. It took three years of my life. Oh my gosh, we should talk about that one day.  

Yeah, I've written about it here and there,  but honestly very quietly is one of the biggest  

transformations Airbnb went through, shifting from  I'm going to go request a book to basically every  

book now on Airbnb is instant. And that was a very  difficult and painful journey. But looking back,  

I don't think Airbnb would've made it  if not for that. And unlike Thumbtack,  

we did it before things were starting to fall  apart. And actually, I was going to say the lens  

that we used that I find really helpful here is,  you should be asking yourself, "If somebody was to  

come into our space and disrupt us and start now  to become the new Airbnb, what would they do?"  

Yeah, totally. And it was obvious that  

it'd be be make it instant, just the way it works.  Welcome to Airbnb disruptor. And so, yeah.  

Another learning there is any product you work  on that involves bits and atoms is exponentially  

harder than products that just involve bits. But  it's amazing how something as seemingly simple as  

make an instant ends up being so incredibly  deep and complicated. And especially on an  

existing business, making that transition while  still growing is just very, very complicated.  

Fantastic learning I'm sure you had as well. Very difficult to change people's expectations  

and behavior. This could be its  own podcast episode, just changing  

marketplaces into an instant experience. I wanted to circle back real quick to the  

first lesson you had there, which is adding new  channels. I think this is a really interesting  

takeaway here. So essentially Thumbtack was  reliant on SEO. Google slash the sword, as  

you described, started changing things so traffic  stopped coming. I think a cool lesson here is just  

if you're reliant on one growth channel, which I  think most companies actually are, I think most  

companies have one main driver, I think a lesson  here is potentially before things start to fall  

apart, especially if you're SEO-driven, start  to explore more practically paid referrals.  

Totally. I mean I think maybe it's, again,  it's kind of living through that. Now,  

anytime I look at a product or look at a team,  it's one of the first things that perks up the  

paranoia of just like, "Oh no. You don't want to  be in that situation. Let's figure out now how you  

start to diversify because you just never know,  like you say, when one of those might dry up."  

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Is there anything else from your time  at Thumbtack that stands out as an  

interesting lesson or takeaway that you  bring with you to the work you do now?  

I would say this, I think especially at the  leadership level, the team that reports to the  

CEO, that group doesn't always have the  opportunity to do a lot of project work together,  

right? You've got your CFO, you've got your  head of sales, you've got your product and  

your engineering. There's just not as often as  natural ways for that group to work together.  

And then when something happens like growth goes  negative, that group is very important. And that  

group's ability to tackle hard things together is  very important. I think that one important lesson  

from that is, no one can be a bystander on product  strategy. Just because you've got product in your  

title doesn't mean you're the only one that should  be thinking about product strategy certainly at  

that level. Certainly not in engineering. The CFO, the head of people, everyone needs  

to have a seat at the table when it comes to  product strategy, what the company's doing and  

what they're going to do to grow out of the  situation that they're in. Because otherwise,  

in those hard times it can kind of be like a,  "What have you done for me lately?" sort of a  

dynamic. And that's just not the right dynamic  to have on that team. I'm not saying that at  

Thumbtack we had the right dynamic, but I think  it was a really important learning in that moment  

of how that team, even if they didn't typically  get as involved in things like product strategy  

and what we're building, how everyone had to be  all hands on deck and really thinking about those  

sorts of problems because it's the only way I  think you can get a whole company and team out  

of those situations by everyone getting involved  in doing their part and pulling on the levers that  

they have in their area in order to do that well.  I don't think it can work in any other way.  

So there's a lesson there. Build  a relationship with the leadership  

team before things start to go awry. That, yes. Certainly that, but I think it's also  

incumbent for people in our roles and engineering  roles to bring strategy to that discussion,  

to that group, in a way that it is possible for  everyone to engage and everyone to internalize  

and understand what it means for their area  and to even have obviously a say in because  

they're on the leadership team at the end of the  day. They should feel like their fingerprint is  

also on the company strategy, and as soon as  it starts to feel like that's their world,  

that's our world. And I think that's true for any  of the functions. It's true for what's happening  

in sales, it's true for what's happening in  marketing. As product managers, we naturally  

need to be the connective tissue across all of  that, but I think the whole leadership team at  

that level should feel like connective  tissue across all of those functions.  

Okay. Let's transition to Facebook. This is I  think an example of 0 to 1. So when you were at  

Facebook, you built what is called the New Product  Experimentation team. I actually thought it was  

called the New Product Experiment Experience team,  but I think it's New Product Experimentation team.  

My understanding is the idea there is, instead  of Facebook having to buy the next Instagram and  

WhatsApp and all the things basically incubate  startups within Facebook in a stabled concept,  

a startup within a startup, create all these  startups within a startup. And as an outsider,  

it feels like it was really fun for a while,  but it hasn't let any amazing new businesses  

for Facebook. Correct me if I'm wrong. I'm curious  what that experience was like, what you took away  

from it, how it went, what you think about when  you look back at that part of your journey.  

I was one of the few folks that kind of joined  that team early and help build that team. How  

it ended up and how it closed down, I am not  familiar with because I wasn't there. But I  

think in terms of was it a success or not  because it didn't build the next Instagram  

I think is a little bit of the wrong bar to set  for things like that. To some extent, it's like,  

"Did the group win the lottery or not? And let's  judge there. Let's judge their success." Obviously  

I'm not saying that discovering something like  Instagram is just winning the lottery, but you  

get what I mean in terms of the rarity of those  sorts of discoveries and those sorts of products.  

I think that that team was very realistic  about what I would say would be the champagne  

level outcomes and/or more like the kind of  beer, nice dinner kind of level outcomes.  

Your wine. Yeah, the wine. Yeah,  

thank you. That's a better analogy. I think we  built knowing those sorts of outcomes would also  

be very beneficial to the organization. So as  an example, one of them is, at Facebook scale,  

doing things that don't scale or doing things that  start out small was just a muscle that was really  

hard to come by, right? It's like any community  product that you build, any kind of social where  

there's community density that's important  early on, any product that you build that way,  

starting with a million users is a really hard way  to do that. At places like Facebook and Google,  

it's like it's hard to run an experiment with a  hundred people. It's not hard, it's impossible,  

right? And so this idea that you would have to  get real small, that you would have to start  

very targeted, that you would have to start with  things that clearly don't scale and don't have a  

chance of being big from the get-go is really,  really hard in an organization like that.  

And so creating that space for NPE to be  able to do that, to be able to help remind  

the organization what are the mechanisms we need  to be able to build and learn that way was very  

beneficial. Even simple things. At an organization  of Facebook size, maybe experiences at an Airbnb,  

it is really hard for product managers, engineers  and designers to talk directly with customers.  

It is basically impossible. You're almost  always talking through some third party,  

some recruiting agency and getting reports  and you're not always in the room. Imagine  

building a startup, like a product from day  one and not being able to sit right next to  

your customer and being like, "Show me how you do  this or show me how you do that.' It's incredibly  

hard. You're looking for such faint signal. The idea that you would try to get it through  

layers of indirection and games of telephone is  crazy, but at that scale, that's what you have  

to do because there's all of these legal concerns  and many other realistic concerns about what you  

can say to who and who you can talk to and what  you can tell them about what you're doing and all  

of these things. So creating an environment where  those sorts of constraints were lifted and were  

different was very beneficial, I think, to the  organization and started to shed a light on some  

of the things that were broken that make it hard  to build 0 to 1 in those sorts of environments.  

I also think it was a really fantastic recruiting  tool. It did build a really great group of folks,  

many of which have left to go start interesting  companies. But I guess what I'm trying to say is  

I think when you're an organizational leader, and  Schrep was the org leader that was supporting NP  

at the time and he's fantastic and really  did a good job of firewalling that team,  

I think you're looking at a set of objectives  and a number of ways that you might help the  

company and the organization. Even if you set  that light on the hill to be like, "Go find  

the next Instagram," many of the things that you  would do along the way to find the next Instagram  

end up being very beneficial to the broader  organization. We saw a lot of that in PE.  

That's a really interesting perspective. There's a  lot of other goals with something like this, it's  

not just find the next massive business. It's the  way I think what I'm getting from this is shine  

almost a mirror on the organization, like, "Here's  the things we can't do with the regular business  

and we have to do something. We have to set this  up in order to try something totally new and  

radical recruiting tool" I think is interesting. There's actually a team at Airbnb,  

the way I described it was, I don't know how many  people know about Burning Man and how it works,  

but there's this trash fence around the side that  catches all the trash so it doesn't go into the  

desert. And I feel like there's teams sometimes  that are the trash fence of the company.  

That's funny, yeah. Where someone's about to  

leave and they're like, "No, go work on this coal  stuff over here in the fringe," which is really  

interesting. But just instill within the company  and maybe help with that. Just keep people that  

are awesome at Meta. [inaudible 00:45:16]. Yeah. You're right that the team didn't discover  

the next Instagram. For what it's worth, things  like Threads and ideas like Threads were in that  

team all of the time. I think that if that team  caught the wave of generative AI and all of the  

opportunities and new technologies there,  I think things could have also... Because  

those are certain moments where you having  small, really motivated, dedicated teams that  

aren't thinking about anything mainline can  lead to faster discoveries, I think that can  

also help. But there were a number of things  that basically ended up becoming features in  

other products and they were just easier, faster  ways of validating and building them because you  

didn't have the constraints of the mainline  product development organization, right?  

For someone that is thinking about trying  to create a startup within a startup,  

something a lot of big companies are trying  to do, is there a piece of advice or two that  

you'd share for helping this be effective?  Maybe one is just the goal may not be build  

the next big business. There's these  sub goals also. What comes to mind?  

God, there's so many. Schrep did a really  fantastic job of removing a lot of these  

constraints. So one is I would say think  really hard about the incentive system. Smart,  

good people, even if they're not trying to,  they end up kind of gaming things towards  

the incentive system. And so think long and  hard about that. So for instance, if you're  

a large organization and you do some performance  management process like twice a year and that's  

how you're going to evaluate and incentivize  people in your 0 to 1 incubator, you've already  

killed it. It's the wrong incentive, it's the  wrong timeframe. It creates adverse selection,  

problems for the sort of people that you bring  in. And so it's hard in an existing organization  

to say, "We're going to take all these company  processes around even how we level people and  

pay them and motivate them. And we're going  to throw them out the window for this group."  

How you build the infrastructure you use,  this is something that the NP team did really  

well. Everyone got to do their own thing from an  infrastructure perspective. Just do what is best  

for the problem you're trying to solve in this  moment, knowing that you're likely going to throw  

away a lot of this code anyway. Being able to do  that in an organization like Facebook or Google,  

if you ask anyone that works on those things, is  really hard. It takes someone like a Schrep to be  

like, "Nope, they're going to get to do this.  Sorry." And so I think that's really helpful.  

For what it's worth, one of the organizations  that we talked to that I felt like was doing  

this in one of the best ways was Nike. Nike  has this incubation lab. It's a completely  

different operating model. They recruit  a completely different type of person,  

very different incentive system. And essentially,  where they end up plugging them into Nike is that  

when they have something into the distribution  marketing kind of growth arms of Nike. But for  

the product discovery process, they're doing their  whole different thing. Once they find some fit,  

then kind of Nike comes in and goes, "Boom.  I'm going to help you explode your fit." But I  

think that the number one thing I would think  about would be the incentive system and the  

adverse selection that that can cause. To me, the most important element of the  

incentive system, and maybe I'm reading between  the lines, is you're basically competing against  

them starting their own thing. And having  upside if things go super well feels really  

important versus, "I'm just going to get a  cool salary at Meta and work on this thing."  

That doesn't lead to the same experience as  a startup where everything's on the line.  

Yeah. And also what time horizons, right? When  you're starting a company, you're not thinking  

like, "In the next six months, I'm going to get  a promo and I'm going to get a good rating and  

things are going to go well." You're thinking on  a different, excuse me, time horizon, and you're  

thinking about an outsized impact or an outsized  incentive. And so I would think about that if  

you're starting things internally as well. Awesome. Okay. Let's move to the final bucket,  

Grammarly, which is where you're at now. The way  I'm thinking about it is this kind of like a one,  

two rocket ship or I don't know, 10. It's further  along than one, but that's where you're at now.  

To me, Grammarly is interesting because it's  one of the very few successful B2C subscription  

businesses. There's almost none. There's Duolingo,  Grammarly. And I know you're doing B2B also,  

but there's so few. There's so many dead bodies  trying to build a business on top of consumer  

subscription. And so I'm just curious. What the  current state of Grammarly? How are things going?  

What do you think has been the key to it being  successful all this time and continuing to grow?  

And what lessons have you learned? I know you  just joined relatively recently, but anything  

you've taken away from that journey so far? We don't talk about it often, but Grammarly is  

a much bigger company from a revenue perspective  than I think people realize. The company has been  

around for 15 years and was profitable from day  one, and continues to be quite profitable. So  

it's a very, very healthy business that is much  larger than folks might realize. And that is  

actually quite intentional because the company  was trying not to be noticed for a long time,  

very intentionally. The fact that you would  have grammar and spell checking in Google Docs  

or grammar and spell checking in Word. People  would often write off the company that like,  

"How is that a business? How is that a feature?  These products already have it." And that was  

very convenient for Grammarly because they  could kind of navigate between these giants  

in tech and grow a very phenomenal business  on this use case that people had written off.  

Now, come the advent of LMS, it's no longer a use  case that people are writing off and sort of the  

dream of the founders that machines can assist us  in communication in this way that they've had for  

15 years, I feel like now the whole industry is  like, "Well, this is obviously how we're going  

to communicate and machines are going to do all  these things for us." And Grammarly is now sort  

of in the center of that hurricane. And again,  I think it's a similar thing where it's like,  

"Well, there's ChatGPT. There's Microsoft  Copilot. How is Grammarly going to have  

a chats?" But yet things still seem like  there's the future. The future is bright.  

And so to your question, I think what has made it  work, I've only been here for 10 months so please  

kind of take this with a grain of salt, but my  instinct is that people really love Grammarly  

because of how it works and where it works. And  what I mean by how it works is Grammarly is one of  

the few products where you just install it and it  makes you better. You don't have to configure it,  

you don't have to manipulate it, you don't have to  change anything about what you're doing. You carry  

on and across all of your applications, across  all of your tabs, you'll start getting pushed  

assistance to you in the right moment. You could  ignore it if you want, no big deal, but it takes  

a very, very small amount of effort to tap on one  of those things, get some value and keep going.  

I think that a product that is that easy  to use, that easy to extract value from,  

but then also that prevalent, how many different  text boxes do you write in a given day? I mean,  

it is not less than 10, it is tens or potentially  hundreds, right? And so it is everywhere and it  

is very, very low effort to get real value from  it. And then the where we work is what I said,  

you don't have to change anything about your  workflow. Grammarly meets you where you are  

and you get value from it. Doing that really  well at this level of quality for a user base  

of this scale, essentially it's like a huge  AI achievement masquerading as a little UX  

innovation, right? But that experience, that  UX that sort of brings AI to the masses has  

obviously served Grammarly really well. I think  those are some of the strengths that we're going  

to continue to lean on to now provide a very  different type of assistance and value that we  

can because of where the technology has moved. The other thing I've heard a lot about Grammarly,  

and Yuri was on the podcast and who led  growth for a long time at Grammarly,  

is just how scrappy the business has been and the  founders have been from the beginning, the fact  

that they've been profitable from the beginning.  That feels like one of the threads through all of  

the successful consumer subscription companies,  is super scrappy, not raising money for a long  

time. Is there anything there that you found  to be really interesting or helpful for other  

folks that are maybe building the space? When you're a team that kind of starts out of  

Ukraine and you're not thinking that there's any  chance that you're going to raise money and why  

would you do that, I mean it really... Back  to our previous conversation of what happens  

when growth goes negative, it really forces  you to focus on the important things. And so,  

like many of the early engineers who are still  here because the company has done so well over  

the years, they think in like, "How is this  work going to translate into revenue?" They  

think about the impact on the business from  even very deep technical work that they're  

doing because I think they were brought up in  this culture where the business doesn't really  

invest ahead of its profitability because it  was a bootstrap business from day one. So that  

enforces everyone to think about their projects  and their prioritization and how is what they're  

doing over the next two months going to actually  turn into more revenue and keep the company  

growing and sustaining. So I think that culture is  prevalent and help Grammarly get to where it is.  

Now, I just want to be really honest that in  moments that we're in like today, that can also be  

detrimental because the business gets to a certain  size, you start getting to law of large numbers.  

You need to start thinking about are there other  products? Are there other use cases? Are there  

other channels of growth? How do you invest ahead  of some of that growth and start to diversify?  

Because at the scale and size that we are and  aspire to be, we're going to have to do many  

more things and service many more different types  of customers. And as you mentioned, we're going to  

have to pull off the motion of B2C to B, kind of  get that product-led sales motion going. So all  

of those things are happening. And thankfully the  business is as strong as it is where we can invest  

ahead now in those things while still maintaining  profitability and a really strong business.  

That's amazing that they're still team members  and maybe I think you said engineers from the  

beginning, 12 years later. I think that says a  lot about the business. And before we started  

recording, they're based in Ukraine and you were  saying that they're going to Zooms, there's bombs  

going off, they have to go into bomb shelters  and then jump on a meeting. It's incredible  

that team continues to operate and the business  continues to do this well in spite of all that.  

Yeah, the team in Ukraine at Grammarly is...  I mean, it's something else. It's a really  

fantastic team. When you speak to many of them,  I think actually the work provides sometimes a  

very useful distraction, but they obviously feel a  lot of pride in the business. They built a lot of  

this business. There aren't yet many businesses  of this size that kind of come from Ukraine. I  

think that that team is incredible and continues  to deliver a ton of impact to the company even in  

the circumstances that they're in. I know for  the founders, a lot of why they want Grammarly  

to succeed and be the generational company  that it can be is for Ukraine, and especially  

in this moment and it's awesome to see how that  motivates them and 15 years on the same project  

is not nothing. That's some serious resilience.  And so I think even in moments like that,  

using them as a way to motivate and strive for  something greater I think says a lot about the  

founders and the team in Ukraine. Absolutely. Hopefully there's a happy  

resolution soon there. I don't know if you  know this, I was actually born in Ukraine.  

Oh wow. I know Odessa.  

Oh, nice. I don't want to talk about that much,  

but it's true. And I just realized we both have  skys in our last name. Lovinsky and Rachitsky.  

So for what it's worth, my dad was  born in Ukraine. He is from Kiev. My  

mom was from Lithuania, so yeah, I also  have some Ukrainian background here.  

All right, so Ukrainian episode. Yes.  

Let me zoom out a little bit and get to the final  couple questions. So thinking about your career  

broadly, I'm just curious if there's any general  advice you share with people to help them have a  

more successful career. Anything that just  generally you find is really important to  

do well or mistakes they make. And this is a big  broad question, but anything come to mind of like,  

"Here's something you should really  try to do more of or less of?"  

Look, when you're thinking about career  opportunities and what job to take, it's really,  

really hard to sniff out really well in a high  degree of certainty like success. I think that  

having a good nose for people and the sort  of people that you can be successful with  

is something that you can develop. What I found  is I always try to prioritize putting myself in  

positions that are going to cause a lot of growth  and learning. And growth and learning can be very  

painful. And you kind of got to be okay with that  and go into that because on the other side of  

that pain I think is the promised land. And that's just served me really well,  

is I can't necessarily predict with high degree  of certainty that this thing's going to hit,  

but I can get a sense of the people around me  and I certainly can find situations that are  

going to stretch me, that are going to force me  to do things that I haven't done where I'm going  

to grow and learn significantly. And over  sort of the arc of my career, I feel like  

that's served me well. So that's usually what I  tell people, is focus on on that if you can.  

I love that advice. I've used this  quote a number of times on this podcast,  

but something I always come back to is this line,  "The cave you fear contains the treasure you  

seek." I'm curious if there's something you  have found about when the pain is too much,  

that you shouldn't pursue that. A lot of people  get into these places where their mental health  

gets hit, their physical health is hit, they're  just doing work they should not, it's too much. Is  

there anything there that you find it's just like,  "Okay, maybe this is too much of discomfort"?  

I mean, I think about a couple of things.  I think in any situation you should be able  

to lean on one or two things that you're really  strong at. That can be the foundation that keeps  

you going while you learn the other things. So  just be wary of situations that are too net new.  

There should be one or two important things as  part of that job going into where you're like,  

"I got this. I know how to do this portion  of it." So as an example, if you've never  

inherited a very large team and you work through  how that works, but the product area that you're  

working on is one you're very familiar with  what's necessary to be good in that product,  

whether it's really good sense of design or really  good sense of analytical thinking, recommendation  

systems, what have you, there should be a  couple of those things where you're like,  

"I got this. These things are going to be a  stretch, but these things, I feel like I've got a  

handle on how to do this. I can always get better,  but I feel like they're in my wheelhouse." And I  

think that tends to allow you to balance the pain  with the areas that you already know and manage  

through in a more balanced and healthy way. It reminds me of that chart I think from flow  

of you want it to be challenging but not too  challenging, and that's where you end up being  

most successful. Is there anything else, Noam,  you want to share or leave listeners with before  

we get to our very exciting lightning round? Yeah, I just think that maybe going back to where  

we first started, Lenny, work on the things that  make you happy, that fill you up. Life is short.  

We're all very lucky to be in this moment. There's  no reason to spend time on things that don't give  

you energy. There's so much to do out there. I  think that's the main thing I would focus on.  

Amazing. And even though there will be things  that you have to do, I think it's important  

to try to find as much of that as you can  because not everyone can just like, "Nah,  

I'm not going to do this work thing. I'm just  going to go on a walk." But I think that's such  

an important point. And we've talked about this  actually a bunch on recent podcasts of just doing  

this energy audit where you pay attention to what  gives you energy and what doesn't and try to do  

more and more [inaudible 01:03:54]- Totally.  

... willing to do that again. With that,  we reached a very exciting lightning  

round. Are you ready? Yeah, I'm ready.  

First question, what are two or three books  that you've recommended most to other people?  

I'm going to cheat on this one and I'm only  going to give you one. I'm only going to give  

you one because I don't want to cloud with any  other. I recommend Build by Tony Fidel. Other  

than it being a good book, one of the main  reasons I recommend it is that my wife wrote  

it. So she wrote it together with Tony. And I  got to see that experience. She's a fantastic  

writer and Tony has a lot to learn from, so I  recommend that book. I think that the part of  

it that was particularly inspiring to me to hear  even more of the details that are in the book is  

just how many times he met failure before he made  discoveries that are now driving so many of the  

things that we do. It's just a good reminder  to keep at it and do the thing that really  

gives you that energy because eventually  you can make that incredible discovery.  

Next question, do you have a favorite recent  movie or TV show that you've really enjoyed?  

I really like For All Mankind, if you've seen  that on Apple TV. And then I just finished the  

last season of Fargo. Every single season  of that series I think is fantastic.  

Amazing. For All Mankind though, last  season, not as amazing a consensus  

that I agree with, but worth watching. Next question. Do you have a favorite interview  

question that you like to ask candidates? I generally like interview questions that allow  

us to kind of do some work together, so I'm  a little bit less on the behavioral "tell me  

about a time when" sort of stuff and more on the  "Let's work a product problem together." It could  

be anything from like, "Let's design an alarm  clock for children." Or lately I've been using  

one. "Given where technology is at, if we were to  rebuild email, how might we do that?" I just feel  

like getting into it and getting into the details  and really watching each other exercise our  

craft I think is really important. I have a whole  podcast one time, if you're ready, about how most  

people don't know how to do leadership recruiting.  And I feel like as I've advanced in my career, the  

interviews for some reason get easier and actually  I can evaluate less about who I am as a product  

leader and whatnot. But yeah, those are the sorts  of interview questions that I typically like.  

Amazing. Is there favorite product you've  recently discovered that you really love?  

It's not recent, but I was a very early  user of Arc and I really love Arc.  

Your window right now is inside Arc. I also  love Arc. We had Josh on the podcast.  

Nice. Just watching the onboarding experience of Arc  

alone as a product person is worth your time. Totally. I love the animation when you download  

something. I mean just like all of the  little things. And if Josh is listening,  

we would like to get Grammarly to work better  with Arc, so please hit me up because I think  

there's a few things that the Arc browser is  doing that make it hard to get Grammarly to  

work either on the client or in the browser. Two more questions. Do you have a favorite life  

motto that you often repeat to yourself,  share with friends or family either in  

work or in life that you find useful? Gosh, for those that know me, this is going  

to share so much of my personality. I think the  first thing that comes to mind is, we are meant  

to struggle. I just feel like through struggle  is how we get better, how good things happen,  

how bonds form, and so I don't shy away  from that kind of life experience.  

I'm going to guess that you're Jewish.  I'm also Jewish. That feels like a very  

Jewish thing to say. I love it. How would you guess, Lenny? It's  

literally written on my face. Yeah.