CHATTING W/ CEO OF $100 MILLION DOLLAR COMPANY | VLOG #18

In this vlog, Ryan Shank documents a day during the second week of Techstars, covering a series of mentor meetings, strategic discussions on pricing, and a successful cold‑email acquisition of his largest paying customer to date. He shares the mentor’s critique that his price points are too low and recommends elasticity testing and tiered pricing models. Ryan explains how content marketing is now moving prospects from the middle to the bottom of the funnel, and he walks through the cold‑email exchange that turned a competitor’s user into a new client, leading to a port‑in of 220 phone numbers. He reflects on a pricing mistake where he under‑quoted a $1,100 deal at $600, extracting a daily lesson: price based on value and avoid underpricing. The vlog ends with Ryan’s routine of heading to the gym, emphasizing persistence and the grind of building a $100 M‑scale business.
Chapters
Sometimes it's like not fun and you still just have to like push through it and just continue going through the motions because that's what makes greatness. Good morning guys, we are on the way to the office. It is 7:30 AM right now. We have Nick coming into town. He should be in New York City around 8:15 today. Then we have a 9 o'clock team meeting. So today's Monday, second week of Techstars. We have a lot of mentor meetings today that we're gonna go through, so. I think you can build a bigger business by helping people take action.
Yeah. That's just like, that's just the wedge.
Yeah.
Right? And it's like, and then what, like what industry do you really want to disrupt? Ding! Good to meet you, Ryan.
Nice to meet you.
Help us out. Transparency usually works in the end if you just keep with it.
Yeah, I want to start like sharing customers and revenue metrics, but like once we get to 100 customers. So I feel like once we're at like 100, I don't know, maybe that's It's all in your head. It's all in my head?
Close of sales, then those 10 phone calls, it doesn't matter what your price per call is, it's price per—
Price per sales.
Yeah. My opinion, being successful at one thing is really goddamn hard. Being successful at two is 3x as hard. I think your price point is totally off. You need to change your pricing page if you're gonna go after that model. If you price it right, these brands will pay thousands of dollars a month to be able to have flexibility.
Yeah, yeah, yeah.
It doesn't mean you can't diversify your model down the road. It doesn't mean that like in year 3, which works much better after you've got, you know, the $10 million revenue line coming from the enterprise, you launch your low-end, like, lead generation service, which is self-provisioning SaaS, and you get all people to throw it, and when you get 5 customers, call our salesperson and they'll devise a little package for you, right? You can get an agency doing $1,000. I think your price points are way off compared to what they actually want to do. Is that—
Off low?
Low. Read up on doing, like, an elasticity study and just try a ton of different prices. Yeah. Because your customers are never going to cross over each other. It's too big of a market. Sure, sure. So try one who needs 30 phones that, you know, $500 and one at $3,000, right? Like, to see how the market reacts. Because there's, again, if you hit the right customer, this is really material information. It helps them identify their marketing, which they will usually spend half their marketing budget to figure out if the marketing is working. So if you get into very large shoppers that need a tool that bridges as quickly as this does, you can charge tens of thousands for the right brand. If you get a big brand, a top 500 brand, they'll pay you tens of thousands to have this tool across their business.
Focusing on marketing, because I want to—
Awesome.
You know, now that I know that, like, hey, we can get the demos set, we can show the demos, like, I want to just feel keep the top of it and find places where we can deploy capital to be able to spend money and then acquire customers efficiently. Cool, man. I really appreciate you taking the time.
Yeah, pleasure. Thanks so much. Yeah.
All right, guys, we just closed our biggest paying customer so far. He was currently— he was using one of our competitors. He switched to us. I want to show you the cold email that we sent him on Friday. So here it is. Basically just said, I saw you guys were using MoneyMailer. I'm curious what you're using to track your phone calls that are coming from, from these different campaigns. He replied that all is well, he's currently using something else and he's good at this time. And I was just like, okay, great, have a great weekend. 1 hour later he sent, change of mind, I want to hear what you have to say. So we sent him a cold email, which is fine. So that was, think of like top of the funnel awareness. But then what happened was he actually did diligence and he saw a lot of the content that we've been putting out, and then that got him interested. So one of the things that I've been saying is like our content marketing right now is actually helping us convert middle to bottom of the funnel a lot better than it— and then if we didn't have anything, right? Because people, you they're not finding us necessarily through discovery, they're not discovering us through it, but once they do discover us, if we can get to them, then it's helping us convert at a higher rate inside of our funnel.
What time is it?
It's 1:30.
How many meetings did you have?
2, 2 or 3. Call it 4, 5, and 6:30.
[FOREIGN LANGUAGE] So I'll just give you a high level.
Um, so the daily takeaway today is to not underprice yourself. Um, I got too— not nervous, but I got too anxious when a customer came in. He was a big customer and he told me he was paying $1,100. I just really wanted to win the sale, so I like just quickly was like, we'll do it for $600. Um, whereas like I probably left a bunch of money on the table. We probably could have gotten him for like $900 or $1,000. So the point is, don't be afraid to, you know, price yourself at where you think that your value is. Most of the time they're not gonna actually pull the trigger because of price sensitivity. That's the daily takeaway today. All right guys, finally leaving the office. Like 9. I don't know why, but I'm going to the gym right now because I feel tired. So I'm gonna go to the gym and it's going to make me feel beautiful. Then it'll be like 10 and I'll like hopefully not have too much energy and then be able to go to sleep. So it was actually a super productive day because our biggest customer, 220 numbers. I think I already told you guys, we just submitted the port request. We're gonna port all of his numbers in from a competitor and get them into our platform. It's a grind though. We're out here every single day hitting it up. It's pretty fun, but sometimes it's like not fun, and you still just have to like push through it and just continue going through the motions because that's what makes greatness. We'll see you tomorrow because we out here every single day. Peace.
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