Drip

“And in fact, the profit that I get, the earnings I get from TinySeed are significantly less than I made when I was building Drip.”

“It's not good, and I was Mr. Swoop in, and I was like, well, obviously I'm a founder, so I can solve all these problems, and it really burned me out, and as you said, it taught my team to just come to me with everything, and it was not good for growing the org…”

“There's a certain amount of repetition and understanding and practice, and it can translate from app to app, but I don't think it, like, just because I was, yeah, Derek and I were good at product at Drip, I wouldn't be good at product at Simewell. I mean, it w…”

“And at one point when we were building Drip and I wanted to talk to some Ex-sales people and marketing people from some competitors of ours who used to work at those competitors, I similarly contacted them via LinkedIn, said, I'd love to talk to you, and said,…”

“Because we know you can build a CRUD app, we know you can build Basecamp, we know you can build Drip, we know you can build MailChimp, right? It might take you a while, These are certain things that will happen. There's no technology risk.”

“At Drip, when we were bootstrapped, I was able to hire some of the best talent in town without paying them as much as they could get from other employers and keep those folks, like none of them left”

“I think it took at least five or six months from the first line of code until it was in, you know, patient zero's hands, customer zero's hands.”

“With Drip, we were, what, 20% more than MailChimp, I think, 20 to 25%, and we were like, well, we were way cheaper than all the marketing automation, you know, Infusionsoft and such was like five, three to 500 and up. And we were like, 50 to a hundred.”

“Myself, zero. I was trying to remember if we did it at one point with Drip, and maybe you remember.”

“We applied and got rejected. They said it's too, they're like, it's too generic, you know, that Drip email is a thing that's existed for the prior art, is what they said.”

“And our competitors, a lot of them were annual only, and, but Drip was super sticky, right? The churn was net negative, and so, you know, we didn't have this particular issue, and it allowed us to kind of outmaneuver and outcompete based on that pricing model,…”

“Even with my audience of 20 or 30,000 at the time when we launched Drip, we got up to seven or 8000 MRR and then plateaued hard with high churn.”

“This is exactly what happened with Drip in the early days, when all Drip was an email capture widget, and a email sequence, and that's all it did, and we were trying to charge 50 dollars a month for it, and people were like, I can cobble this together with oth…”

“We sold Drip. Part of it, I was unhappy with, you know, the fact that I was managing 10 people. I would have kept doing it. The other part is that we had a bunch of inbound interest, and then we got an offer that we kind of couldn't refuse.”

“Every time that I was doing more work than I wanted to be, it was always like, this is a season, this is not permanent. I don't know if this season is a month, or if it's five months, or six months. I never did it for a year straight like that. I did feel stre…”

“Lightweight marketing automation that doesn't suck was the H-one of DREP for years. So what does that imply? That implies, and then I named, because I wrote the whole copy for that long form landing page, I named Crap. Who was it? It was Infusionsoft. It was M…”

“So I bet 11,000 dollars on .NET Invoice in oh five, oh six, It was a tremendous bet. It was a money I had just painstakingly worked hard to save nights and weekends. Then I bet 30,035 thousand maybe with legal fees on Hittail in 2011. I bet 200,000 dollars bui…”

“Even if you hear the story of Drip, how I sent out 17 emails and I got 11 yeses.”

“And as we launched Drip, I overextended myself Financially, because I believed that I could find it just right off the bat. I was going to launch right into product market fit.”

“We were growing two grand of MRR per month, and then five grand of MRR per month, and then 10 grand of MRR per month, and we hit seven figures, and we were doing well”

“People have asked me, like, do you ever regret selling drip? And I've never had a day where I regretted, but I do regret the way that I operated during those years, and the way I let my own mental health deteriorate”

“One of the reasons that we sold was I was like, how far can we take this before we plateau? I don't know. I mean, I could do some math on it, but it, and I saw that, and then I was like, how are we going to get past that plateau that is coming? It wasn't month…”

“Like, Drip has more than 10 X'd since we sold it. In fact, it 10 X'd within probably two years, maybe three.”

“After we sold Drip, we sold it to Leadpages and they had a 40 person marketing team.”

“And we found that we had a two to three X improvement of conversion for those instantly.”

“When we launched our visual workflow builder that took Derek five months to build, that was an unlock, and we went from growing, From, let's say, three to 5000 MRR each month, up, it went up to 10 K a month.”

“We did not even have a Shopify integration, and 15% of our customers were e-commerce.”

“I call that false demand the curse of the audience. And if there's two curses to it, one, you tweet it out or you email your list and everyone's like, oh, I kind of want to check out what they're doing and everybody's really interested. And then they're not ac…”

“The reason we did is because I saw the ESP market, and I was like, MailChimp, and HubSpot, and whoever else, you know, Infusionsoft, and everybody charged per contact or subscriber. That's probably the way to do it. And I was aware of net negative churn and al…”

“The valuations for, like, almost no revenue were, like, ten million, and I did put, I put, like, five grand into one of those, and I put 10 grand into another, and all of them either went to zero or returned, one returned me 11 grand for my 10 grand investment…”

“When we were building Drip, you know, I was about a 150 to 200,000 of my own money, and that got us to product market fit, and then no other money raised”

“When I sold Drip, I experienced a barrage of congratulations, while mentally, I was almost at my breaking point.”

“What we noticed was on the lower end, you know, if someone was going to pay us 50 dollars a month or a hundred dollars a month, those are our cheapest plans. It had to be product led. I was not, we weren't going to do a demo. We were, you know, there's just th…”

“I don't think there was a single Kind of traffic source, so to speak, that was more than 15% of our monthly trials, and so we had like, yeah, and it was all time, and I was running, I was like, dealing with Facebook ads, I was paying somebody to run those, we …”

“Drip actually launched with four different ICPs, and we actually narrowed over time.”

“I believe we did this with Drip because we went from, we had three or four different email providers that we were using that were APIs that, that sent emails. And it would take us a matter of weeks to switch and we were sending hundreds of millions of emails a…”

“This is one of the bigger mistakes that I made in the early days of Drip, is I hired really junior people, and it was, you know, I use the excuse that, well, this is all I have money for, and I want people to be local, and really, to be honest, in Fresno, Cali…”

“I mean, the first product person we hired, we were doing several million in ARR and his salary was a 165,000.”

“15% of our customer base was e-com, and we had never marketed to e-com.”

“My last SAS drip, we had 12 customer, full-time customer support people by the time we had, I think it was 30 or 40,000 free users.”

“With Drip, I was spending a non-inconsequential amount of money, maybe a thousand a month, maybe more on Facebook ads.”

“Even with Drip, I talked about it being a 50 dollar starting price point. Most of our growth, especially as we got later, were folks paying us between 500 and 2000 dollars a month. It was the big lists that made, that moved the needle for us, and that's the pa…”

“Drip was, what, the 300th email marketing application, and our competitors who, like, I think VentureBeat did a top 10 Marketing automation providers, maybe it was like top 15, and we were number, I honestly forget the number, like 10 or 11, and everyone ahead…”

“Like, I was, I already had some experience, I had a lot of marketing, I had a lot of sales, self-funded, a 150 to 200 grand in cash to get us there.”

“We were literally losing deals over just that, and they were significant deals, they were hundreds of dollars a month, obviously thousands of dollars in ACV, at a time when we were, I think we built it when we were a 20 to 30 K MRR, And I knew that there were…”

“In the early days, getting a Loom or equivalent recorded for your support or for your KB is way faster to do. Over time, it is essentially a type of debt, video debt, documentation debt, because we did that with Drip in the early days, right? Instead of writin…”

“Even again, when we left Drip, it was doing tens of millions a year with tens of thousands of customers.”

“But the reality is, I mean, in the final days of Drip, when I was there, we're doing tens of millions a year in revenue. Team is 125 people or so. We were getting close to, I think it was about one 75, 200 feature requests per month.”

“And so I would just be pretty honest with them and be a human upfront about this is who I am and this is the goal of the call rather than trying to talk them into it or trying to act like someone that I wasn't, right? I didn't try to channel some fake extrover…”

“There were some folks charging like 10 grand to migrate and, you know, get your stuff set up on Drip.”

“So in the early days of drip before we launched, I had 3400 people on an email list.”

“Dude, I even remember, so Leadpages acquired Drip, they had a 170 employees, and I remember getting in there, and they were, they had Leadpages, and they had Center, which was this product they were trying to get off the ground, and some people there kept sayi…”

“Your customers will come to you with feature ideas. Don't build those features. Dig in and find out what is the job that feature is trying to accomplish.”

“That was our visual workflow builder in Drip, and it solved literally 50 feature requests that had come through, you know, in the span of a year.”

“So when we were growing Drip, people would Say, do you have split testing? Because we need to split test everything, and eventually we built split testing and one percent of our users used it, but everyone thought they wanted it.”

“With Drip, we did do a Drip two point O launch because the one point O launch happened in say November of 2013. And we peaked at eight or 9000 MRR and then plateaued because to your point, our pricing wasn't figured out. Our features were not there. We didn't …”

“Answering questions on Quora, which is something I did in the early days of Hittail, in the early days of Drip, and even a little bit in the early days of TinySeed, and I did that myself.”

“With Drip we had 3400 people on an email list, and I think I started doing it in, I think the first launch was to 300, and then we did another 300, and I realized we could totally handle it, so then we went up to like four or 500, and I believe by the end we w…”

“I talked to 17 people. I got 11 yeses. For me, the tipping point was at 10.”

“With Drip, we would take a customer's ebook or a series of blog posts and we would turn them into an email mini course. So it was copying, pasting, formatting, some things like that. And so I had essentially a support person who took that over and would build …”