With a career spanning five successful startups, including Performable, Compete, and Ghostery, David has built a reputation for creating high-growth products and scaling world-class teams.
David shares how his upbringing in an entrepreneurial household influenced his career and how Drift was born out of a desire to modernize outdated sales and marketing tools that no longer fit today’s buyer-centric landscape.
He explains that traditional lead capture methods, like forms and email nurture sequences, are obsolete in a world where customers expect real-time, 24/7 access to solutions.
David emphasizes that true innovation isn't just about software — it requires a complete cultural and data model shift, similar to how the social graph disrupted CRMs.
David advocates for embracing mentorship and collective knowledge rather than learning every lesson through struggle, as the most important insights often come from others, and the earlier we internalize them, the better.
Website: Salesloft
LinkedIn: David Cancel
Instagram: dcancel
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Transcription:
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David Cancel Teaser 00:00
Thinking about starting Drift was that those tools that exist, which are most of the tools that we all use today in marketing and sales out there, were really built for this world that doesn't exist anymore.
And what I mean by that is that a world where the company has all the control of the sales process and the consumer or the buyer has no control in the sales process.
And I think what we observed was that the world had flipped upside down and that now the customer has all the power and has infinite supply of choice, and they can buy anything anywhere 24/7.
Intro 00:33
Are you ready to hear business stories and learn effective ways to build relationships, generate sales, and level up your business from awesome CEOs, entrepreneurs, and founders without listening to a long, long, long interview?
If so, you've come to the right place. Gresh values your time and is ready to share with you the valuable info you're in search of. This is the I AM CEO Podcast.
Gresham Harkless 01:00
Hello, hello, hello. This is Gresh from the I AM CEO Podcast, and I have a very special guest on the show today.
I have David Cancel of Drift, an author of conversational marketing. David, it's awesome to have you on the show.
David Cancel 01:10
Thank you so much for having me. I'm excited to be here.
Gresham Harkless 01:13
No problem. Super excited to have you on. And what I want to do is just read a little bit more about David so you can hear about all the awesome things that he's doing.
And David is a serial entrepreneur, podcast host of Seeking Wisdom, and angel investor and advisor.
He's best known for creating hyper-growth products and product teams at companies such as Drift, HubSpot, Performable, Ghostery, and Compete.
David was named the top ranked CEO by USA Today, has been featured by media outlets such as the New York Times, Forbes, Fortune, Wired, Fast Company, and has guest lectured on entrepreneurship at Harvard, Harvard Business School, MIT, MIT's Sloan School of Management, Bentley, and other universities. David, are you ready to speak to the I AM CEO community?
David Cancel 01:56
I am super excited to be here. Thanks for having me.
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Gresham Harkless 01:58
No problem. No problem. Super excited to have you on. they kick everything off. I wanted to hear a little bit more about what I call your CEO story. What led you to start your business?
David Cancel 02:08
Sure. So, this is actually my fifth business that I've started. So I, if I go all the way back in time, my parents immigrated to the US, and they both worked for themselves, and I kind of grew up in that environment.
And I think that had a lot to do with me wanting to start a business. And back in the day I'd had no idea what a business was or how to start a business or any of these, these things.
But like five companies later, I think I've figured that part out that at least that little part of it out.
And I started this business because, I basically wanted to fix some of the problems that I think I helped create in the other companies that I had created. And so, trying to right a wrong and bring something new to the market.
Gresham Harkless 02:47
That makes perfect sense. And definitely, I think you're doing pretty well if you're five companies in.
So, it's great to hear that you not only were able to solve problems within those companies, but you found other problems that you're able to solve, too.
So, I wanted to hear a little bit more about these problems and what you're doing with Drift and how you're helping to solve them.
David Cancel 03:04
Sure. So, all of my companies that I've started and been a part of have been basically marketing and sales software of some type or another.
And what I realized when I was thinking about starting Drift was that those tools that exist, which are most of the tools that we all use today in marketing and sales out there, we're really built for this world that doesn't exist anymore.
And what I mean by that is that a world where the company has all the control of the sales process, and the consumer or the buyer has no control in the sales process.
And I think what we observed was that the world had flipped upside down, and that now the customer has all the power and has infinite supply of choice.
And they can buy anything, anywhere, 24/7, 365, and so now companies have to change the way that they market and sell to this new reality. And that is the basis of why Drift exists.
Gresham Harkless 03:55
Nice. And that definitely is, exactly right in this day and age, especially with all the opportunity and the technology.
In this day and age, everything's literally at your fingertips. So, if you don't like this, you can move on to that. And you're saying that Drift is created in order to combat that.
David Cancel 04:09
Exactly, and the truth is that most companies in the world, although theoretically they may understand this, or intellectually they understand this, they haven't changed the way that they market and sell yet.
And because all the tools in the market were built for that old world, and so we're trying to usher in this new shift that has already happened, as you said yourself, like it has nothing to do with us, it's already reality, but we're trying to create software that makes it easier for people to make this transition.
Gresham Harkless 04:37
Nice, nice. And could you drill a little bit deeper and tell us a little bit how that software is doing and how like somebody who thinks they may be kind of ushering in that technology. But may not be doing it as much as they could, how they could be doing it.
David Cancel 04:48
Yeah, so if we think about the typical sales process today, and marketing process, like you get people to your website, you make them fill out, if it's not e-commerce, which most businesses are not.
You make them fill out a form, you put them, you send them a bunch of emails, you nurture them, at some point you decide that this person would be a good fit for your business, and then you get back to that person.
But that usually happens days, weeks, sometimes even months later. And again, that worked in a world where you were largely a monopoly or had very few competitors, and so you can control that process.
But today's world, you have an infinite number of competitive solutions. And so, in today's world, what we do with Drift is say, Don't do that.
Instead, try to be available 24/7, 365, seven days a week on your website. And instead of directing to the forum, have a conversation with that person because if you have sales people, you've never sold anything until you had a conversation.
So that is the core thing. Instead of putting hurdles in front of them, enable the conversation.
And of course, we need to sleep and we're not available 24/7, so Drift enables and is built with bots so that the bots can have these conversations and can help people while your team is asleep. But then at the same time, provide you with this 24/7, 365 experience for that buyer.
Gresham Harkless 06:14
That makes perfect sense. And it's funny because it sounds like, and correct me if I'm wrong, a lot of times FAQs were created because a lot of people have the same questions over and over again, but you don't really have that conversation, that back and forth that I guess Drift provides.
David Cancel 06:28
Exactly. You're not getting the context, which is important about where is that customer? Where can I meet them? What is their real question?
And FAQs existed for a long time and they exist today and they're fine, but FAQs are really driven by deflecting. Again, forums are deflecting, FAQs are deflecting, so that's about scaling a relationship versus having a conversation, understanding the context, and trying to solve for that customer.
Gresham Harkless 06:56
Absolutely. That makes perfect sense. And now I wanted to ask you for what I call your secret sauce, and it could be for you or for your organization, but what do you feel kind of sets you apart and makes you unique?
David Cancel 07:07
In the market today, a number of things. I mean, we were the first in, as far as we know in the world, to have those type of bots for sales qualifications specifically on the website.
And so, like that was, there are now other companies who have emulated that, but we were first in the market to do that.
We have built our entire company around this paradigm and this shift. You cannot just tack on a feature or add something to your product and make it this new thing because it's a fundamentally different data model.
Just like you had Salesforce as a CRM, and that's a cloud-hosted database paradigm.
And then you had new companies come in like Facebook and LinkedIn that use the social graph, which is an entirely new data paradigm.
And Salesforce could not take that technology and put it on Salesforce with like Chatter or one of their other products and make it LinkedIn or make it Facebook, you're always going to have winners in the categories that emerge.
And so, this is an entirely new category, entirely new data model. You can't really tack this onto something else. And so, like you have to build your company around this conversational database idea and that conversational data being the core of everything.
Gresham Harkless 08:19
That makes perfect sense. And it definitely sounds like correct me if I'm wrong.
It's not just a kind of a software technical thing. It sounds like it's a core principle for a company and culture that you want to be able to have those conversations and nurture, as you said.
So, it's also, you know, the technological part obviously, but also some of the culture as well.
David Cancel 08:37
Absolutely. So that's why, and theoretically, like when we look at, companies like companies, startups should never exist.
New entrants and markets should fundamentally never exist. If, because if you look at a company, theoretically, they could do the same thing.
They could copy exactly that. They could come to the same conclusion. They can build this thing. They can rejigger their products. But we all know that that's not true.
And, the reason that new entrants exist and startups exist is because most companies cannot get out of their way because they've aligned all their incentives within their company to work along the paradigm that they're in and the products that they're in today, and they can't just wholesale shift into a new model. That's why this exists, right?
If everything was theoretically perfect and efficient, then new entrants would never exist, and those existing companies would continue to shift and take all of the market share. But we know that's not true.
Gresham Harkless 09:31
Absolutely. And that's why the word disruption exists. Definitely. So, I wanted to switch gears a little bit and I went to ask you for what I call a CEO hack.
And this might be an Apple book or a habit that you have, or even something that we don't know about drift, but something that can make you more effective and efficient.
David Cancel 09:47
Yeah, I think I'd say there's a bunch of things, you probably heard everyone's talked about, like routines and habits and morning practices and all that. So, I won't go into that. But I do think that's important.
For me, the most important thing is that I'm an avid or addictive reader or obsessive reader.
And so, I read a lot. And the trick that I will pass on to the audience is that you don't have to read a book the way you were taught in school, from a table of contents to the end of the book at one go.
You can pick up multiple books, and this is what I do. I read multiple books at a time, three to five books at any given time, and I'm bouncing in between those books.
As I lose interest in a book, I'll put it down. I'll open up another book, and I will read that, and then I go back or revisit the original book.
And what you learn is that, look, every time you read a book, and you can read the same book every few years, and you'll get something different out of it because you're bringing a different context to that reading, right?
And so, things emerge out of there. The other thing that happens when you read multiple books at once is that those ideas start to associate across each other, and you start to think of new combinations, new patterns, and new syntheses of ideas by reading multiple books at one time.
And they can be nonfiction and fiction. Totally unrelated, but those ideas kind of pollinate and you come up with even better ideas.
Gresham Harkless 11:11
Absolutely, it kind of speaks definitely to the evolution of us as people or companies or where we are in our lives as well too because you look at it from a different perspective and I love that you touched on as well that a lot of times we're kind of, indoctrinated might be the right word, to basically read a book from table of contents and understanding that that's not necessarily the best way to always do it.
So now I wanted to ask you for what I call a CEO nugget. And this is a word of wisdom or piece of advice, or if you can hop into a time machine, what would you tell your younger business self?
David Cancel 11:42
It's probably, I think it's, it's probably what everyone says, which is like, relax, don't take it so hard, but like, don't be too crazy.
But I think that's, it's, you know, most advice I find, I spent a lot of time thinking about advice that I've gotten over time. It sounds trite. It sounds like we ignore it.
And, you think like, oh, there must be a more complicated answer to this. And what I realized over time is that that's not true.
That the fundamental lessons that you need to learn in life, most of us know before we're even a teenager, early in life, we already know what they are.
The problem is that it takes us most of us a lifetime to actually learn those lessons, because it's easy to gloss over the simplicity in those lessons, right?
Your grandmother, if you spend time with your grandmother when you're a kid, your grandmother probably imparted everything that you need to know in life pretty early in your life.
But it takes us years and years and years of resistance and then fighting and then finally mother nature teaching us, either through pain or we get smart in some cases and learn from others.
That these true, that these simple lessons about, whether it's treating people the way that you want to be treated, whether it's, don't be too hard on yourself and, like, uh, enjoy life.
Like all these things sound trite and sound like creating cards, but like, they are the most important lessons in life.
Gresham Harkless 13:08
Yeah, absolutely. And, now I wanted to ask you my absolute favorite question, which is the definition of what it means to be a CEO.
And we're hoping to have different quote-unquote CEOs on this show. So, David, what does being a CEO mean to you?
David Cancel 13:20
Well, for years, I would tell people that it means like, then I'm the chief experience officer, right? Like, and I get experience for all the people, right?
Experience for our customers, experience for our team members, experience for our investors, our community, like that's really what I spend my time on, and other times, especially earlier in the history of my of a companies, I would say the CEO is the chief explainer officer.
And so, I'm kind of in that phase right now with Drift, which is what I mean by that, is that most of the time, as you scale a team and you're bringing a product or service to market, you spend most of your time explaining, right?
And you start to learn, like, Oh, okay. This is why people who write speeches and politicians and others like they repeat simple messages over and over. And as a CEO, you have to; that is a lot of what you're doing.
Whether you're translating for your investors, the public markets, your team members, your customers. you're explaining, explaining, explaining over and over again.
And one of the hardest things that I've had to learn is that I don't like repeating myself naturally like that. I like saying something once and I kind of think it's obvious and that is exactly the wrong thing and the wrong way to approach this when you become a CEO.
Gresham Harkless 14:36
Absolutely. It's just like any, marketing or sales. Sometimes you have to say it seven, eight, nine, a hundred times before it actually comes in.
And people kind of dictate that and understand it and it becomes like the gospel, I guess you could say.
David Cancel 14:49
Yeah, I didn't believe it. I didn't believe that again, another kind of idea that, it's taken me many years of pain to figure out, which is, I didn't believe that was true. And now I'm like, wow, it is so true.
Gresham Harkless 15:03
Absolutely. Absolutely. Well, David, I truly appreciate your time. What I want to do is pass you the mic, so to speak, see if there's anything additional you can let our readers and listeners know, then of course, how best they can get ahold of you, get a copy of your book and hear about all the awesome things you're doing.
David Cancel 15:17
So, to find me, I'm DCancel on Twitter, Instagram, everything. So I'm pretty easy to find. And, we offer free copies of our book.
If you go to drift.com, DRIFT.com/book. And, I would say definitely don't take too hard on yourself, budget CEOs, alphas, listening to this thing, and you don't have to learn everything on your own.
Most of my career has been brute force, AKA pain. You don't have to do that. You can learn from mentors. You can learn from books. You can learn from other people.
Most of what we need to learn in doing this job has been figured out because most of this job involves people, and people have not evolved. And so, the lessons are all there.
Gresham Harkless 16:05
Absolutely. Well, I definitely appreciate that. I appreciate your time, and we'll make sure to have the links and your information in the show notes as well.
But David, thank you so much. I hope you have a phenomenal rest of the day.
David Cancel 16:15
You too. Thank you so much for taking time with me and letting me be on the show.
Outro 16:19
Thank you for listening to the I AM CEO Podcast powered by CB Nation and Blue 16 Media. Tune in next time and visit us at iamceo.co. I AM CEO is not just a phrase; it's a community.
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