- The CEO of HubSpot, Brian Kardell, describes how he manages being an introvert while leading a public company.
- Kardell takes measures to manage his introversion, such as working from home alone every Wednesday and taking daily naps.
- He blocks off his calendar on Wednesdays and schedules breaks in the afternoon to recharge and catch up on work.
- Kardell mentions that being an introvert as a CEO can be challenging, but he has learned to manage it.
- He and his co-founder, Dharmesh, both introverts, balance their roles with Kardell taking on more public-facing responsibilities.
- Kardell credits the book "Quiet" by Susan Cain for helping introverts feel more comfortable in managing their energy and setting boundaries.
- He shares how he and Dharmesh met in business school and started HubSpot, initially focusing on a suite of applications for law firms before pivoting to a marketing application for everyone.
- Kardell explains their unique insight into marketing, which focused on the changing behaviors of consumers and the need for marketers to adapt their strategies.
- When it comes to pricing, Kardell admits they initially had no idea and randomly settled on $250 a month, but now they have a more sophisticated pricing structure.
- If starting over, Kardell would have implemented a freemium model from the beginning, allowing customers to try the software before purchasing.

- HubSpot was built on .NET Nuke and hosted on a server under a desk before AWS existed
- HubSpot initially provided consulting services on website optimization and social media before transitioning to building software to automate these processes
- The early days involved helping customers set up and edit their blogs, including adding humor to their content
- The SEO tool WebsiteGrader.com was a popular feature that compared a user's website to their competitors' websites
- HubSpot initially underestimated the demand for customized websites and focused on templates, but eventually realized the importance of customization
- HubSpot gradually transitioned from a consulting company to a software company, raising funds along the way
- HubSpot focused on putting as much advice and features as possible into their software, but also created a content machine and HubSpot Academy to teach users
- SEO is an underrated marketing strategy that can be a goldmine if done right
- The future of marketing involves a focus on customer experience and lighter go-to-market models, similar to successful B2C startups
- Cold calling is largely ineffective and outbound marketing is declining, while inbound marketing that matches the way people want to buy is becoming more important
- The startup costs for starting a company have significantly decreased, making it a great time to start a business.

- Scaling a company is difficult in today's competitive market
- Breaking out in the market requires a go-to-market experience that is 10 times better than the competition
- Building a great customer experience and word of mouth does not require a lot of money
- Creating content through blogging, podcasting, or video casting can help build an audience and establish expertise in the industry
- Renting ad space is not as effective as creating your own content or assets
- Finding a co-founder with complementary skills is important for success
- The internet disproportionately benefits small businesses over big ones, as it provides opportunities for outsized marketing advantage without a lot of money
- Hungry competition and the long-term value of content creation helps keep a company motivated
- Assets such as links, followers, and pages on the internet are important for long-term success.

- The speaker discusses their dislike for renting assets and the importance of content as an asset.
- They explain freemium as a strategy and how it has been successful for their company.
- The speaker reflects on their experience implementing a freemium business model within their company.
- They discuss the importance of having a large market for freemium to be successful.
- The speaker talks about the shift their company made from being sales and marketing-focused to being more customer-centric.
- They discuss the importance of investing in product development to reduce churn and create customer delight.
- The speaker shares their experience in changing the voice of their company's content to appeal to a broader audience.
- They discuss the importance of metrics such as visitors, leads, customers, churn, cost to acquire a customer, and total lifetime value.

- The speaker discusses the importance of self-improvement and receiving feedback through coaching and annual reviews.
- They mention the challenges of transitioning from a startup to a mid-stage scale-up and the need to let go of control as a founder.
- The speaker shares their experience of giving up their role as head of product because they realized they were not good at it.
- They talk about the importance of humility in their company's culture and how they have noticed a shift towards humility in the CEOs of newer companies.

- HubSpot CEO Brian Kardell discusses how he manages being an introvert while leading a public company.
- He takes measures such as working from home alone on Wednesdays and taking daily naps to manage his introversion.
- Kardell credits the book "Quiet" by Susan Cain for helping introverts manage their energy and set boundaries.
- He and his co-founder balance their roles, with Kardell taking on more public-facing responsibilities.
- Kardell shares the history and growth of HubSpot, including their transition from consulting to software and the importance of customization.
- He emphasizes the importance of customer experience, content creation, and the shift towards inbound marketing.
- Kardell discusses the benefits of a freemium model, the importance of finding a complementary co-founder, and the value of assets such as links and followers.
- He talks about the challenges of scaling a company and the need to invest in product development and customer delight.
- Kardell reflects on the importance of self-improvement, receiving feedback, and humility in company culture.

Brian Halligan is the CEO and cofounder of HubSpot. HubSpot builds software for marketing, sales, and customer service.

https://twitter.com/bhalligan
https://www.hubspot.com/

Kevin Hale is a Partner at YC and cofounder of Wufoo.

https://twitter.com/ilikevests/

The YC podcast is hosted by Craig Cannon.

https://twitter.com/craigcannon

Y Combinator invests a small amount of money ($150k) in a large number of startups (recently 200), twice a year. 

Learn more about YC and apply for funding here: https://www.ycombinator.com/apply/

***

Topics

00:00 - Brian's an introvert that likes to work from home. He also runs a public company. How does he do both?

1:45 - How does he manage his calendar as an introvert?

3:45 - How Brian met his cofounder Dharmesh

5:45 - The first project they worked on together

7:00 - What was their unique insight when starting HubSpot?

8:25 - Pricing in the early days

9:00 - How would he have priced HubSpot differently knowing what he knows now?

10:00 - HubSpot's first customer

12:00 - Important early features

14:20 - At what point did they shift entirely away from consulting?

15:05 - Providing advice as content vs in the product

16:00 - SEO is underrated

16:45 - Trends in B2B and marketing

21:30 - Inbound marketing and audience building advice

26:25 - How did Brian know that his cofounder was right for him?

27:45 - The internet disproportionately benefiting small businesses over big ones

28:45 - Keeping your company hungry when you're big

29:15 - Building assets for your company 

30:20 - Freemium

34:00 - Structural pieces of HubSpot Brian would have changed if he did it again

37:00 - Creating the voice of your company

39:30 - Early metrics they tracked

40:05 - Having a coach and reviews

41:30 - How Brian's changed as a CEO from the beginning

42:24 - What was the hardest thing to give up as CEO?

43:30 - Humility

So Brian, I've listened to a few of your podcasts and on 1 of them you described yourself as an introvert who likes to work from home.

That being said, you manage a public company.

I am an introvert and I just try to manage it as best I can.

I'll tell you 1 thing that's interesting about HubSpot is both founders are introverted, but 1 is far more introverted than the other.

And 1 of you has to be the front man to the band basically and Dharmesh, my co-founder, does not want to be that.

So I have to kind of play the front man to the band.

And so I have to manage my introversion a little bit more carefully than he does.

And so what practices do you put into place?

Well, I have to manage my energy cause people drain energy from me.

So a couple hacks I have, every Wednesday I work from home all by myself, just my dog and I.

And no meetings, no calls, no Zooms, no nothing.

I just work on projects, try to get caught up and recharge my batteries.

I tend to take a nap pretty much every day around this time actually.

take a little snooze and we have a nap room at HubSpot and I kind of think of a nap as like your brain is just running around and lots of things are going on in your brain.

And it's a time for your brain to just kind of settle down.

And I picture these little mini men with brooms going around sweeping up all the stuff and organizing it.

Everything gets settled down in my brain and then back to work a half hour later.

does that affect your calendar management?

Like normal CEOs, there's nonstop barrage of sort of meetings and people you need to interact with.

And so how does that affect you or how do you handle your calendar differently when you're an introvert?

Yeah, I basically just block all that day Wednesday so no 1 can book a meeting there.

I have an admin that manages my calendar and she'll typically manage little breaks in the afternoon maybe at 2 or 3 or 4 which she'll know if I have a packed day I'm going to need a little breathing room to kind of catch my breath, take a nap, catch up on some emails, and kind of get back at it.

And then on a daily schedule basis, do you leave in blocks for like solid focus work, or do you just leave it open to like, okay, I can interact with everyone every 15 minutes, you know, like that maker schedule, manager schedule.

I typically leave in blocks of time where I can recharge and think and catch up on email and do some of that stuff.

Yeah, that's always the part I struggle with, like the required socializing, as someone who's introverted.

It's part of the job, but I don't like to recognize it all the time.

At what point did you realize you were gonna have to do something differently to make that work for you?

You know what, when we both got started, there was a, we were in a, It was called CIC in Cambridge, Mass.

And there was a couch outside our, just happened to be a couch outside our office, and every day I took a nap, and everyone gave me crap for

But, I don't know, it just worked for me.

I think what helped a lot of introverts, I don't know about you guys, is when that lady wrote that, what was your name?

It's like, oh, I'm not as strange as I thought I was.

And I didn't feel as badly about wanting to take this time away.

Didn't feel as badly as it was saying, you know, I've been in meetings all day.

I know we're supposed to have dinner tonight.

And I think a lot more introverts felt comfortable doing that after that book came out.

Yeah, I think labels can also be a crutch.

And I felt that after that book came out.

It's like, sorry, I'm an introvert, I don't do this stuff.

My co-founder uses it even more than I do.

You can be an introvert and CEO of a public company.

It was the night before business school at like a cocktail get-together at the Marriott Hotel.

And I was on my second Sam Adams, that's what we drink back there in Boston.

And a woman comes up to me, a blonde woman, and she starts chatting with me.

And I just assumed she was a student, but she asked me a lot of questions, like really pounded me with like an interview almost.

And nice enough conversation, it goes away.

And I just thought she was a student, but what was going on there was Dharmesh was there with his wife, that was his wife.

So what Dharmesh does, my co-founder, is he hides behind the plant in the corner of the cocktail party, sends his wife out to interview potential people that he might want to talk to and then goes and chats with them.

And the scouting report on me was, you'll never like him.

He's into the Red Sox, he's into the Grateful Dead.

You don't even know who the Grateful Dead is and you don't even own a pair of Red Sox.

Man, and so what convinced him to go over

We didn't actually chat that day based on the scouting report, but there was a class we took.

We both went to Sloan together and we sat next to each other in the class and the teacher assigned a project on stock option pricing or something like that.

And he said, well, why don't we work together on the project?

And we went out for Indian food that day.

And we discovered we had a lot in common.

We both liked doing business with startups and with small business owners and trying to turn small businesses into big businesses.

Back then we were into something that's passe now, but it's called Web 2.0, sort of a old meme that we're really into.

He had started a couple of companies and I had worked in a couple of startups and done pretty well.

So we kind of started on the journey on that project we did together at Sloan.

Project was about how to price and value stock options in a company.

What I'm trying to think of is, after that, what was the first little project that you guys worked on together that was outside of school that made you realize, oh, we're the right ones to be working together.

Yeah, we started talking about HubSpot at lunch that day.

It was something called LegalSpot, not HubSpot, which was going to be a suite of applications to help you manage your law firm.

And we tinkered with it all through business school.

We put it in the business plan competition, the 50,000 ounce, $100,000 business plan competition.

We worked on it in a class called New Enterprises.

We tinkered with the project for a while.

And then when I graduated a year before he did actually, he was on a different track than I was.

And I spent about 9 months in a little venture firm as the EIR, and we tinkered with it.

You know, we'd meet once or twice a week and work on the idea and pitch it to law firms.

And we kind of zigged and zagged a couple times.

And then during that time we decided, well, it's not about building a suite of applications for a law firm.

1 of the applications we were talking about was a marketing application was how do you get found on the internet?

How do you get found in Google and social?

How do you grow business, and all the law firms are interested in that.

Instead of being a vertically specific application for law firms, we were going to build a marketing application for everyone.

What do you think your unique insight was at that point?

I mean, At the time, I'm sure there were way fewer companies doing internet marketing.

I think we were pretty good at framing it as to everything in HubSpot is rooted in end user behavior.

So normal human beings, how are they changing the way they live, how are they changing the way they work, how they shop and how they buy stuff.

And at the time there was a sea change going on.

1, humans were changing the way they work.

They were living in Google, living in social, living in the blogosphere.

The second shift that was going on was humans were becoming very good at blocking marketing out.

Caller ID, spam protection, ad blocker, all that kind of stuff.

And so we came up with the idea that marketers needed to turn their playbook on their head instead of doing outbound old school stuff.

How do they pull people in and match the way they market with the way people shop and buy?

And then we pulled it together in a suite of applications for mere mortals who would want to do this, that didn't have a bunch of developers running around, that could do it and grow their business.

And I think part of it was we framed it as this inbound thing versus outbound, the versus really works on the internet.

And the other thing that worked was pulling it all together and building something not for technologists, but for mere mortals.

There's a lot more mere mortals out there than technologists.

And how did you guys contextualize yourselves and figure out pricing in the beginning?

I remember I came back from 1 of my meetings and I said to Dharmesh, I said, you know what, I actually think this guy wants to buy something from us.

And we went back and forth and we randomly came up with 200, very scientifically came up with $250 a month back then.

So I went back, got the credit card later that afternoon for $250 a month.

And HubSpot was $250 a month for the first 6 years of HubSpot, we didn't change it at all.

And then we got more sophisticated with our pricing and now there's a lot of different products and price points.

If you were to start over again and think about pricing, knowing what you know now, how would you have thought about pricing?

I think I would have flipped it on its head.

We had designed HubSpot to be a model where you sell it through inside sales.

You use inbound to pull lots of leads in, hand them to inside sales reps, have them sell it.

The most recent version of HubSpot these days, half our leads come through that.

The other half really come through a freemium model where people can try it, use it, bang on it, and then they just like consumer software, they will, and I think this will happen all B2B enterprise software will turn into consumer software, where they'll come over to Tripwire and they'll buy the software in a much more natural way.

And sales reps can call on customers versus on prospects.

And in what degree, like what was HubSpot, the first customer?

Well, because this was pre-AWS as well, right?

We built it on .NET Nuke and hosted it on a server under our desk.

And I would tell you the early days of HubSpot, the software didn't do much, and so customers would ask us for help.

And so we made up for the inefficiencies in the software by giving them good advice on how to optimize their website and how to get going in social.

And what we didn't want to fall into was the trap of building something that was a consulting company.

And so we said all the stuff that we're consulting on, how to set your website up, how to get links into your site, how to set up your, and it wasn't even Twitter and Facebook, it was Dig and Reddit back then, how to get everything set up appropriately so you can grow.

How do we take all that stuff we know and build software to do it to automate it?

That was basically the model in the early days.

And he was setting up a site in my, our first sales guy, Mark Roberge, sold them on HubSpot.

And he said, yeah, our co-founder, he's going to get you all set up in the software and he'll help you with anything you want.

So I got the account and I helped set up his blog.

And I remember he wrote his first blog article and he said, can you set this up and get it on the interwebs?

I said, well, why don't I teach you how to do that?

And so I got him on the phone, I'm setting it up.

And he said, what do you think of my article?

And so I read it and I read through it and read the whole thing and he said, well, stop.

And he said, I want you to read it out loud.

I'm reading through the article, the thing out loud.

Not only helping people set their blog up, but actually posting it and editing it.

Was there any feature that you guys developed in the early days that ended up being this killer feature that all of a sudden changed the direction?

Yeah, the SEO stuff we built was pretty cool in the early days.

We built a tool called WebsiteGrader.com that's very popular still.

You go to our website, websitegrader.com and you type your URL in and you type your competitor's URL in, and it gives you a score on how inbound your site is.

How good are you at getting found in Google?

Was the competitor check the actual big thing that helped make it really drive people to actually want to change?

It was 1 of them, because you put yours in, then you put your competitors in, then you taunt them.

Or what I would do is I'd show up at a sales call and I'd put your company in Y Combinator and then I'd put in whatever, 500 startups, Mass Challenge, and I would use that as information.

That was really motivating to get people to move.

I think about selling and modern selling, it's about helping people understand that they have a problem, and really making that problem real to them.

So in the early days of HubSpot, that was a tool to really point out, boy, you're falling behind in the competition.

You're falling behind all these other folks, what are you gonna do?

Well, let me show you a demo of our software.

I think another really cool thing that you guys do is that you eat a lot of your own dog food.

Like you guys kind of try to practice as much as you preach.

Is there anything that you guys initially had a hypothesis around that didn't work out?

That you're like, oh, we think this would be sort of a good thing to do.

And then when you put it out there, it was like, oh, that didn't work out so well.

1 thing that we thought for sure, we were right about a lot.

The 1 thing we were dead wrong about is we thought the whole world, we thought this idea of people having customized gorgeous websites and bespoke websites was just a foolish idea.

Like I don't have a custom car for example.

There can be a thousand templates out there.

But it turns out everybody wants their own custom website.

For the longest time we were like, stop worrying about the design, use our template, put your blog on, put your site, you're going to be happy.

And so at what point did it feel like you really shifted to a startup from a consulting company?

Because in the beginning you're spending all these extra hours doing things that you definitely can't do forever.

But, you know, a year in, a year and a half in, we were probably almost all software.

Okay, and at that point were you profitable or had you raised money?

We raised a million of Angel in Boston pretty early on and then we did a Series A.

Back then we did, what was a big Series A was 5000000 bucks, now a small Series A.

What was the split between, you talked a bit about, in the beginning it felt like a consultant that you're giving all this advice.

You said you eventually turned that into software.

But I imagine some of it was just turned into content.

What was the split between actual software features versus content you had on the side to help people just get going, like documentation, et cetera?

We tried to get as much of it in the software as we possibly could.

We also created a university, HubSpot Academy, and we made really high quality, really nice videos to teach people about this stuff.

And I still think of HubSpot as a little bit like it's code, there's software, there's content, all that content out there and there's a community around it.

That's sort of how HubSpot works underneath the covers.

David Walsh Yeah, I mean, because it makes sense with the website competitor comparison.

It's the most underrated marketing thing there

We get 10 million visitors a month through SEO.

Because I feel like a lot of people know, do you think it's just people have turned their attention away from it?

I think people are really focused on ads.

And ads have gotten a lot better over time and people perceive that SEO has gotten harder over time.

And I just think people have lost focus on it.

And if you do it right, it is a goldmine.

Yeah, I mean That was a huge motivator for us to do YouTube versus just a podcast.

Because YouTube is just like, there's not a lot of good content out there.

I mean, you've done some videos, but even once you get to the second page when you search your name, it falls off pretty quick.

So I want to kind of get back to the beginning stuff, but we're going in the direction of trends, and I want to talk about that stuff too.

So in terms of the future of marketing, where do you see the big trends happening?

Yeah, if I thought there was, if the arbitrage opportunity when we started HubSpot in 2006 was generating leads online.

I don't think that's the arbitrage, there's still an arbitrage opportunity there now, but there's a new 1.

And I like to describe the new 1 with my morning routine.

So I get up every morning on my Casper mattress, I put on my Warby Parker glasses, I take my phone and I turn on Spotify, and then I shave with my Dollar Shave Club razor, and I put on my Trunk Club outfit, and I take a lift to work.

And what's fascinating to me about my mornings is those 6 startups, and they are startups, are all very much part of my life and have completely disrupted the incumbents in those space.

And they've done it with much lighter go-to-market models and a gorgeous end-to-end customer experience.

And I feel like all those industries are being disrupted dramatically by people who are just better at customer experience, step function better.

And I think that's coming to B2B in a big way.

If you haven't already figured that out in B2C, you're kind of screwed.

See all Y Combinator transcripts on Youtube

HubSpot CEO and Cofounder Brian Halligan with Wufoo Cofounder Kevin Hale