Interview ‘Gleb Polyakov Co-Founder & CEO Nylas’

The Extra Mile interviews Gleb Polyakov, Co-Founder, and CEO of Nylas, about his journey in entrepreneurship and his advice for aspiring business owners.

During our interview, Gleb shared insights on several key topics, including the importance of reaching out for advice, overcoming analysis paralysis, and the pitfalls of micromanagement. His experiences offer a fascinating look into the world of entrepreneurship, emphasizing the value of mentorship, the necessity of taking action, and the significance of trust in building successful teams.

TEM ( The Extra Mile): Tell me a little bit about yourself and a little bit about your company?

Gleb: Yeah, absolutely. So, I’m Gleb Polyakov. I’m the CEO and co-founder at Nylas. We’ve been at it for 10 years now. Just hit that milestone. The team size is around 150. We’ve raised about $180 million in venture funding so far. And the core product we build is we’re a DevTools company. We have an API and some front-end components, but basically, we connect your back-end to the contents of communication. Email, calendar, contacts, meeting transcripts from your Zoom, your Google Hangouts, and your online meetings. And we give you the ability to extract all the meaningful information from that and then put it to work. Build the automation, the workflows that then power your end tool. So, primarily we sell to software developers. We’re an infrastructure product, and people incorporate our toolset into their end products. So, it’s been a fun growth year for us. We’re now, we hit a nice bandy metric of we’re now over 1% of all the world’s emails going through our servers, which is really fun to see. It’s one of those things you can get excited about that you didn’t expect when you’re first starting the business.

TEM: What kind of inspired you, you know, to start this, especially ten years ago when, you know, tech was at a very different space?

Gleb: Yeah. So I had just sold my previous business, which was a hardware play in the coffee space, of all things, and was looking for a new opportunity. I was talking to folks in my network and got connected to a thorough mutual friend at MIT, my now co-founder, Christine Spang, and was just super impressed by her. She’s just one of the smartest people that I know and just a generally great human being. And she had already built this super cool system out of just email. Some calendaring, but mainly just email. So the product platform was a lot more nascent ten years ago. The original idea was to build a newer, better email client.

So a better Outlook, a better SuperHuman for those in the Outlook space. It turned out, though, that one, we took a very MIT-ish approach of like, well, let’s solve the general problem first. Let’s make the toolset that makes it super easy to build anything on top of email. But the business side was a lot like it. It was a cool technology. We built this great toolset, this great API. We open-sourced that. We also had an email client that we put out there. The email client as a business did great in the first six months, right? We got about half a million users pretty quickly. And then they pretty quickly all shared. As a business, people don’t love paying for email multiple times. Yeah. And the folks that love trying new email tools.

TEM: Was there a pivotal moment, especially in the early stages where you’re like, okay, we’re going to change the direction?

Gleb: Yeah, I mean, we shut down the email product, which was our 100% focus, and switched to the APIs. In terms of pivots, as far as pivots go, we got pretty lucky in the sense that our core underlying tech remains unchanged from the beginning. But yeah, we scrapped years, I don’t know, probably 10 million dollars of spent money at that point to transition to the API. It was the right call, but it took a lot of rework. Focus-wise, product-wise, engineering-wise, go-to-market-wise, it was basically building the company from scratch in a lot of ways.

TEM: What would you say in your experience for an entrepreneur that just started maybe a year or two years in their business, do you have any advice that you’d like to give that you wish you had known first at your company?

Gleb: Definitely reach out to folks who are one or two levels above you and ask for advice and their experience or really any number of levels above you. People are really interested in helping if you present them with, like, if you ask for help in the right way. And the right way is don’t waste their time, be respectful, and be specific, like, hey, I know you did this thing, I’m currently doing this thing, running into this challenge, is that something that you’ve navigated in the past before or have seen before or can help me with? Definitely keep reaching out to folks and just learning their stories. When asking for help from folks, it’s also much more useful, usually, to ask for their experience and not for them to necessarily, don’t ask them to solve your problem, ask them, like, for their understanding about the problem, the space, but it usually happens, like issues they’ve seen, they’ve overcome, that tends to add a lot more useful information and that tends to lead to longer relationships because it’s a little bit less transactional. People like talking about themselves at the end of the day more than they like, you know, doing work for someone else for free.

But the, uh, what else? Go out there and do it. I see a lot of entrepreneurs really get stuck before they launch their product, their business. Analysis paralysis. Yeah. Thinking they have to get it right. Yeah. Thinking they have to have everything locked down. The data. All the data. All of it. I saw some number, and I don’t have the backing of it, but it was something like two-thirds of entrepreneurs never launch a business. I was like, in what way are they entrepreneurs, though? Yeah. Are they entrepreneurs? Just get out and sell it. Even before you have built it, just get out and sell the thing, and you’ll learn so much more from that than you will from anything else. And what else? Honestly, the most common sort of pitfall, that’s not a major one, that’s like a medium one, that I see first-time founders especially fall into is micromanaging their teams. So, I mean, decide how big a company you want to grow. Are you trying to become, like, a billion, trillion-dollar company? Does that mean you will have, like, 400,000 employees eventually? Or are you going to stay small, a team of five or six people? Those are different businesses. Yeah. No one business better than the other. To get to that large scale, you’re going to have to give up a lot of ownership. To stay small, you get more. Are you going for money? Are you going for the mission? Are you trying to build a product? Figure that out. But once you have a team, the common thing people do is they say, like, it’s all on me, the weight’s all on my shoulders, I have to figure this out, I know what’s correct and where I want to take it, all of which is true. And the end behavior is deep micromanagement of their teammates from a place of fear. From a place of fear and not knowing what to do, and them spending a lot of time at lower levels doing a copy edit, and especially folks who haven’t really been, like, don’t have years of management experience themselves, don’t understand how that just devastates ownership for the team. And, like, it makes you a miserable person to work under. And I say that as, this is what 90% of people I’ve seen, often, myself definitely included, and you’re gonna have to trip over this one. But if you can shorten the time that you spend learning this lesson by focusing on, like, okay, what actually motivates people, where can I set trust in terms of metrics for success for the role, instead of getting to this mindset of, I need this person to prove that I can trust them before I give them ownership. Because that is just, like, the slowest way to build the team that they turn up and running.

TEM: So, let’s talk a little bit about, you know, culture, you know, doubling down on that, kind of what you’ve mentioned. What would you say are some key values that are important for your company and your staff?

Gleb: The ownership, the accountability piece is big for me. I really feel that the job of leadership, at any level, but the job is, here’s where we’re going, here’s why we’re going that way, the how’s up to you. Here’s the context, here’s the direction, you tell me how you’re going to do it, basically. And that gives the team an ability to say, well, I mean if that’s where we’re going in the context, wouldn’t it be better to go over there instead? Like, if that’s why we’re going that way, go there instead. And that’ll accomplish the goal better. Well, the more you treat people like adults, the more you get adult behavior. It’s just, we talk about AI models all day, but every human currently is better than the AI. Most humans are better. And so, like, you’re paying them. Ask them to do the harder work. And if you don’t think they can, why’d you hire them?

The trust piece is really interesting because it’s like when that becomes the failure mode, I think it’s because the success criteria hasn’t been defined well enough. And it’s like, you wouldn’t care about trust if there was like, I just need these four things from you. I don’t even care how many hours you work a week. You work 80, you work 10. I just need these four things this week. You get it, you’re good. It’s like, where it starts having issues is when there are unstated expectations that they don’t address quickly enough, and then it becomes tense. It’s like a whole thing. But no, culture values, they’re real important. They touch into the whole fabric of how the teams work together. They can be words on a page, but I think it’s more these informal processes that carry through culture. And they basically boil down to, what do you get promoted for, what do you get fired for? What do people get publicly praised for, get told you’ve done a good job? Oh, what a great question, what a good analysis. And what do you get told, hey, don’t focus, don’t do that, don’t spend your time there. What do you get fired for, actually, because that’s its own amount of information, the way things are done. It’s like, this team, we’re really, really protective of our data. Good or bad, this is how we do it, and we’ve got to keep doing it. So being aware, sure of the stated values.

For us,  Trustworthy!  I love those values. I think, in my mind, that also, like, summarizes what it means to be a good person. But it’s never going to be enough to just put down 4 or 13 or however many words on a page and have people understand what you mean. You have to, especially in a leadership position, the image of farming comes to mind. But you have to, like, really prune and cultivate it and pay attention to that, like, people dynamic aspect of it. One, from a utilitarian perspective, because you want it to work. Two, because as a leader, you’re going to have to go into a firefighting mode. Like, some crunch, super important thing is going to have to happen. You’re going to have to have the whole company sprint or reorient quickly. And you’re going to have to be able to have their trust and understand how they all work to make that change and have it all work quickly. But also just makes it a clearer, better place to work, I believe.

TEM : So, in your opinion, are there any trends or technology that you think is going to really shape your industry within the next 5 to 10 years?

Gleb: I mean, AI is the biggest one. Part of it is, how can I improve my leverage today? Plenty of ways to do that. For our company, we found, oh, just engineering. Software engineering, AI assistance. I can pretty confidently say we’re at least 30% better. At least 30% better with the same team than we were a year ago because of the better tools. Then, on the customer success side, a lot of the initial tickets, and a lot of the time spent on the easy customer questions can be automated away. That leaves the human resources that are able to do the better work, or the harder work. For me, I do think we’re getting to a place where, call it 3 years, 5 years from now.

I have to decide, alright, do I hire another salesperson, or do I hire an AI system for this? Do I spend $100K on a software developer, or do I spend $100K on AI coding? That’s not going to be directly that one-to-one. Fine. On the sales side, for example, people are still going to want to buy from people. I don’t think we’re 5 years, or even like 15 years away from AI purchasing, or like, being a thing. You’ve heard of them, they sound so real. And they can even mimic your voice. But I don’t think anybody at like, I don’t know, American Express, or even a startup is going to be like, hey, just tell the AI to buy whatever it wants. They’re going to want to renew the purchasing. They’re going to want to buy from a person. But you can get so much more out of one salesperson today than you used to be able to get out of a team 5 years ago. That trend is going to continue. I kind of see, especially for enterprise and B2B sales, this whole SDR, BDR, AE distinction is going to kind of collapse in on itself. Already there are a lot of tools that let 1AE do prospecting and outbounding and personalization work, finally, in a good way. These are all still fairly nascent trends.

TEM:  Is there anything that you’re excited about or that you’ve seen here a Collision?

Gleb: Oh, so much. I mean, I love, love, love the… There are the, like, alpha and beta companies here. Yeah. The stages, where there’s, like, all the startups. It is so cool just walking through and seeing all the ideas that people are putting together. The themes are there. The energy, too. The energy is great. The energy is so, so good. It’s a great conference, I think. Yeah. But no, I mean, I’ve seen, like, four pretty cool things. And, like, the… What’s interesting to me is… We keep lowering the barriers of entry to starting a business. It keeps getting easier and easier to build something cool. Yeah. Using the analogy of, you know, there’s Squarespace, there’s Shopify. Yeah. You can sign up in a day. Maybe two days. Maybe two days. Yes. Your website, your store, your whole business flow. You just got to fill in what it is and what it’s selling. Yeah. Will it be the world’s best website? No. But it’ll be, like, fairly good. Yeah. Pretty good. Yeah. More than you need to get started, for sure.

The same thing is going to happen for most apps, pretty quickly. Most apps are pretty straightforward, their databases, their cloud interface, and some straightforward business logic around that. That is a very, not easy, but constrained type of possibility space to automate through AI tools. So okay, if the barriers of entry are getting lower and lower, if the markets keep getting bigger, look at the number of people that have internet access. That’s $4 billion-ish, $4.5 billion-ish right now, doubling over the next five years to almost everyone, as Starlink and everything else goes up, our whole species in one common marketplace. That’s kind of cool. What are you going to do about it? What does that open up for you? And seeing all the small companies out here just doing their best and actualizing finally ideas that used to be vaporware like ten, five, three years ago, it’s cool. It’s nice to see the pace of progress accelerating in real-time.

Learn more about Gleb Polyakov here