From JD to CTO to CEO | Darin Brown from Docket

As a software developer and team leader, Darin Brown has seen all sides of the startup world through several companies—big successes, hard failures, acquisitions, and the one thing binding them together, a lot of unproductive meetings.

It was the desire to solve this problem of meetings that led him to co-found Docket, which offers a software tool for making meetings more efficient, directed, and ultimately worthwhile.

On this edition of UpTech Report, Darin takes us through his journey from a junior developer, to a CTO, to the co-founder and CEO of his own company, and what he’s learned along the way.

More information:

Docket was co-founded in January 2019 by CEO Darin Brown. Prior to co-founding Docket, Darin served as the CTO of Angie’s List and Vice President at Salesforce and ExactTarget.

As in his previous roles, Darin laid the foundation, building an amazing, experienced team and board of directors. Team members bring a variety of experience including co-founder, CTO, marketing technology, mergers and acquisitions, marketing, compliance, customer management, and product-led growth. From early-stage startup, growth-level, and enterprise experience, our leadership knows what it takes to start companies from the ground up and nurture them to success.

DISCLAIMER: Below is an AI generated transcript. There could be a few typos but it should be at least 90% accurate. Watch video or listen to the podcast for the full experience!

Darin Brown 0:00
We’re trying to solve your individual pain first, right? So that is the focus of our message. And that’s the intent of the product is to make sure that you when you sign up and you begin using it within the first experience, you get the value of it.

Alexander Ferguson 0:21
Welcome to UpTech Report, I’m excited to continue our conversation now in our founders journey series Leaders Insights. To hear out Darin Brown, the CEO and co-founder of Docket has gotten his company to where he is today. And there’s always tons of insight from before you start, whatever venture you’re working on right now. And a quick recap of of docket. It is a meeting focused platform perfect for making the most out of every meeting, that is their marketing slogan from their websites. Great there. And if you wanna learn more about it, check out our first part one of our interview, but Darin, I like to dig a little bit deeper. Now, to hear your story. Truly, how did you get to where you are today?

Darin Brown 1:03
You mean, like, you know,

Alexander Ferguson 1:04
go back? Yeah. Let’s go back

Darin Brown 1:07
to how much time you have. So, you know, I, I started in software development, right, it really the right time. And it was the mid 90s development, software development was really starting to become a career. I’m basically based in Indianapolis. And there was a lot of really cool startup activity, even back in that day. So I joined a startup, as a junior developer, and had a great ride. That startup was called Double tech software. I was there for 11 years, we IPO. And it was just fantastic, you know, move through the ranks to kind of management and build lots of product and lots of teams and had a fantastic time. And I thought that was great. Let me try that again. And I jumped to another startup that I won’t name but it did not go so well. And I called I saw the flip side of the startup world, but you know, I’ve just I’ve had a great ride, I have been able to stay in prod in tech in Indianapolis my entire career, I spent a few years, the company called ExactTarget, that was on just a rocket ship and got acquired by Salesforce. And I moved over from there into a CTO role at Angie’s List. Angie’s List is based in Indianapolis, and we had a really good time building a completely brand new tech stack and moving 3 million members over in just a couple of months. So it was it’s been an awesome ride. And that really is I you know, talking about what doc did. Part of my attraction to this problem was all the different companies I’ve been in the different cultures and the different levels I’ve been in one thing that was consistent was the unproductive meetings that I had to attend. So seems like a real problem that’s worth solving.

Alexander Ferguson 2:45
Now, this is your first venture that you’ve co founded. Yes. Okay, so exciting. Lots of lessons learning happening right here. But you’ve already been in multiple startups who have seen it happening. But now you’re at the helm having to lead it. Yeah. So I’m intrigued. First off as far as funding wise, have you bootstrapped? Or is this VC funded? Or this is

Darin Brown 3:07
VC funded? Yeah. high alpha, venture capital venture studio is essentially the co founder and the main VC Packer.

Alexander Ferguson 3:15
What would you say is the biggest mistake one could make when seeking funding?

Darin Brown 3:23
That’s a good question. It’s really not understanding the mechanics of the VC world, and how funding works and how dilution works and those types of conversations. We really there’s a lot of good information out there, the VCs, you know, if you look over the their sites, there’s a lot they provide, you really need to educate yourself. There’s a lot of pros to it, right? The ability to get that backing, and really get started and grow very quickly if you’re successful. But you know, you just have to be aware of what the trade offs are and how to approach those

Alexander Ferguson 3:58
from the pitching side, how did you prepare and what you think is one of the most important lessons you learn from pitching and sharing that the story concept to get the funding.

Darin Brown 4:11
So I had no contact role, not really sales background at all, and pitching and selling, right. So it is you have to be on all the time, you have to be excited, you have to be energized. And you have to tell that story 1000 times, but be excited every time you tell it right? It is a story you have to have a you know, the narrative has to be crisp, it has to be understandable. And it has to you know, mean a lot as you’re as you’re talking about it. So I would spend a fair amount of time on the deck itself and look at there’s lots of good examples out there. You want to keep it short, you want to tell a good story. You want it visually IMPACTFUL, which is a lot of thing or a lot of times people don’t really think about but that visual, those visuals tell a good story as well. You really need to put all of that together in order to have that strong conversation

Alexander Ferguson 4:57
as you then go ahead and get the funding You start to build the product. How long did you spend in development?

Darin Brown 5:05
Well, we spent a couple of months in development before we put it in prints and families hands. Right. So that was step one was, again, this is a docket is a solution to a problem that almost everybody has. So it’s not hard finding potential customers, right? So it really was, hey, people I know in the industry, friends, family, try this out, let me know what you think. And we had probably three or four months then on that, as we iterated through their feedback before we were ready to call something MVP, and put up a website, and, you know, have an open beta and just start to drive people to it. And so overall, between like, start to website available to anybody and product available, is about six months. Okay,

Alexander Ferguson 5:50
how did you? How did you go about assessing the initial price? And kind of determining that?

Darin Brown 5:59
Yeah, that’s an excellent question. So what I did was really look at the competitive set look at like products, look at products that have a very rich feature set and offer maybe conceptually a lot more value versus those are just maybe note taking apps and where they’re at and try to just compare and contrast what value I thought we were bringing to the to the individual and the organization and where we should fall on that spectrum. I will say pricing is one of those as a startup, you should not be afraid to test it all. Most most startups undervalue what they’re offering is. And that is one of the easiest ways to increase your overall ARR is to increase that price by $1 to a month, users, if they find value in the product, they will they will not bat an eye to do that, but it’s meaningful to your company.

Alexander Ferguson 6:50
Speaking of customers, it’s kind of important to get those, what have you seen as far as common mistakes, you one could make you’ve seen you can make or you have made, that you would advise against when it comes to marketing in today’s world.

Darin Brown 7:04
So docket is taking the product like growth go to market strategy, meaning it’s freemium. So the bulk of our users come in on the free product, right. And so whatever we’re doing has to be cost effective. In that manner. We, our long term strategy is SEO, we want to have that organic search and have people find us that way. The other leg of that stool is the product referral. So Docker is a product where I use it in the meetings, the other participants in the meeting, see it, they log in and start using it for their own meetings. And it just kind of spreads virally, both internally within the company and in between companies. So that is awesome. But in order to kind of prime that pump and test out the messaging, don’t neglect the paid aspect of things, right. So there between LinkedIn and Google ads, and Facebook, there’s lots of opportunity to really test the messaging there and find what works. And make sure when you’re testing it, to treat it as a test to turn it off. And when it’s not performing. And you, you know, you over index when it is performing.

Alexander Ferguson 8:08
As far as this world that we’re in the where intention, it’s, it’s, it’s really difficult to grab someone’s attention, because there’s so much overloaded of what’s happening. And the distractions, any tactics that you found that work well to grab attention and keep it.

Darin Brown 8:25
Yeah, with you. I’ve said this couple times. And I’ll say, say it again, with the product lead growth aspect of it, we’re trying to solve your individual pain first, right? So that is the focus of our message. And that’s the intent of the product is to make sure that you when you sign up and you begin using it within the first experience, you get the value of it, it’s not something where there’s a big implementation for it, and it’s three or four months before it really starts to to be beneficial to the organization. It’s really day one. And so our messaging is really around more the concepts of you know, how it affects you. And the emotions that it brings to you that you feel better about your day and you feel better about your meetings, the amount of visibility that your peers have with the product, right and how you’re perceived to have run a better meeting in a more organized meeting. Right? That’s impactful to you from a career standpoint, those are the two things that we try to to do and it’s really to your point about grabbing their attention is that emotion that you want to latch on to right I want to feel better about my day. Especially, you know, with COVID going on it’s we’re in a unique spot and that our product is ready made to make your work day more efficient as you spend hour after hour in zoom calls. So it is that emotional kind of you’re frazzled. You just want to want to be

Alexander Ferguson 9:54
Yeah, you want to be released from that motion that you have. You make an interesting point right there if you truly want to grab Attention in today’s distraction, very distracted world, tying it to an emotion is is is key, you know that the immediacy, oh wow, that’s I feel that emotion I don’t want it or that’s emotion I do want to feel Yes. And then most likely to, to get better attraction love it love it. Now to accomplish your vision you need a good team as well, building a team, any mistakes or bad things that one could make in hiring that you would advise against the void?

Darin Brown 10:32
I would say. So, I was guilty, pre COVID have the mindset that I really wanted to build local, especially a startup world, building that culture is critical to the early success of the company, in my view was you know, if I’m hiring local, I much better foundation, which to build the company. And then as we expand the company, as we’re successful, maybe we’ll go and look at remote employees. All bets are off now. Right? So I mean, my my blinders are off. So even as we convert COVID, and we go back to a more mixed mode, the fact that we can hire anybody from anywhere, is something that I think we should have done in the beginning, and really focused on your the talent pool is so large, when you do that, it really opens it up. And you shouldn’t be afraid of even at an early stage company of doing that. You can manage the cultural aspects of the company, effectively, as long as you’re paying attention to better if they’re local or remote.

Alexander Ferguson 11:31
That’s a powerful, powerful insight right there. How big is the team today?

Darin Brown 11:37
Tim? Counting me 10

Alexander Ferguson 11:39
As obviously you grow, the culture itself will change and develop? How How have you found in previous companies now into where you are now you kind of know imagine the steps and and what to expect and feel any insight there of what you need to pay attention to to make sure you’re not losing something?

Darin Brown 12:00
Yeah, I mean, it really comes down to your actions. I believe as a leader and the actions of the leadership team, it doesn’t matter what you say, what culture you write down on your mission statement, or your your employee handbook, or, you know, the what you say during the all hands meetings or anything like that. It’s how you carry yourself day to day, your interactions with the employees and the teams. That’s what’s going to carry through. And that’s why I know, looking back on it, you have those interactions, regardless of the person sitting next to you, or they’re sending the 1000 miles away, right. So that really is what drives culture. It’s more your actions, people pay attention to what you do much more than what you say. And as long as you’re cognizant of that, and honest to yourself and where you want to go. You’ll be okay.

Alexander Ferguson 12:41
Any thoughts that pop in your head from the previous companies that you’ve worked at? Where you’re like, wow, they should have done that differently? How are you and you weren’t managing at a time but you experienced it that you would advise around it?

Darin Brown 12:57
Yeah, so the the unnamed startup, they wanted to build this, this was mid 2000s. And they wanted to build this, what they viewed as Silicon Valley kind of culture where people are working all hours, night and day. So, you know, they essentially mandated the Friday afternoon beer, right? So at the end of the day, you were highly encouraged to meet as a group and socialize versus letting people do that organically. You know, like the the manager meetings were held at Sunday night at nine o’clock, and went till midnight, right? And it was this kind of forced, you know, let’s build this high energy company, when you really have to do that organically. That’s not something

Alexander Ferguson 13:44
that you mandate, mandating a culture like that, I can see that may not feel that well. Then go looking forward from here going to next year. What kind of challenges do you see you’re going to need to overcome in order to continue growing?

Darin Brown 14:04
It really is. So we’ve we’ve taken the playbook of do things that don’t scale to heart, right? So we’re small team, and we’re trying to just try and get started. And if you let the idea that you have to build everything that that will scale. You know, before you can, you can do anything you’ll never get you’re never getting that completed, right? So we’re doing a lot of things that are unnatural if we really scale. And so that’s the big challenge is how to move those things from kind of more than manual and the just brute force method to you know, automating that to making sure it just happens as we grow. Because we still have to we have to do all of that plus we have to move forward and do all these new things as well. Right? It is, is that rocket ship ride that you hope you’re on it’s it’s a lot of pressure. It’s but it’s pressure in a good way. Right? It is fun when you’re successful.

Alexander Ferguson 14:58
As far as I know, having right knowledge to keep growing. Are there any books, audiobooks podcasts that you are currently reading listening to right now or would recommend a previously that you have read?

Darin Brown 15:08
Well, I will give a plug to a podcast called Rita lead. I do listen to it often. It comes out weekly, and I’ll be transparent. It’s my brother’s podcast. He’s been doing it for several years. Go check it out. But he interviews, a lot of top name authors on leadership books and kind of productivity books and those types of things. And just listening to that I know immediately when I went to go buy that book saves me a lot of time, you get a lot of insights, just listening to it. So I do listen to that quite a bit. And I have a long stack of books sitting on my nightstand that I need to work through.

Alexander Ferguson 15:47
Last question for you, Dad. What kind of technology innovations do you predict? We’ll see in the short term next year, so and long term next 510 years?

Darin Brown 15:56
Well, I think, again, the COVID has changed, or I was COVID is sped up a lot of activity in technology, right. And so I think the concepts of AR and VR, and how they occur in the workplace, is really going to come to the forefront. If you think about like, operating spec meetings. Right. One of the challenges that that people still have of meetings is the whiteboarding session. And we you know, the docket team, we’re all remote right now, we do have an office and the only time we go into the offices if we need one of those whiteboarding sessions, right. There are a lot of technologies that exist today and a lot of products that attempt to solve that digitally, right. But it’s really missing the point. It’s not the interaction of drawing on a screen, or drawing on a whiteboard. And being able to see that in real time. That’s the challenge. It’s the human interaction of seeing, reading the body language and seeing that sideways glance, and you know, those kind of little, little items that you’re going to miss. On the screen. Yes, small cues. And so I think if you start to think about it, and start to enable our layer on some VR, AR into that where it is, is you’re seeing individuals and you’re seeing the medium at the same time, in a much more realistic way than what we can do now. That’s when it gets really exciting to me.

Alexander Ferguson 17:21
I am excited about that potential actually interviewed a few different VR companies. And it’s that now hold like step which hardware and other things have to catch up. But we are getting closer. Thank you so much, Darin, for sharing your insight the lessons that you’ve learned over these years. And now there’s, there’s more to learn. So we’ll have to check back in a few in another year or two, and see what else we have to share. Yeah, thank

Darin Brown 17:44
you for having me on.

Alexander Ferguson 17:45
And thank you everyone else for joining us on this founders journey, a part of our UpTech Report series. Our sponsor again for today’s episode is TeraLeap. If your company wants to learn how to better leverage the power of video to increase sales and marketing results, head over to We’ll see you guys next time. That concludes the audio version of this episode. To see the original and more visit our UpTech Report YouTube channel. If you know a tech company, we should interview you can nominate them at UpTech Or if you just prefer to listen, make sure you’re subscribed to this series on Apple podcasts, Spotify or your favorite podcasting app.



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