Episode #038

When Your Side Project Blows Up with Dawson Whitfield of Logojoy

What would you do if your side project made $30,000 in its first month? This is the exact situation that Dawson Whitfield found himself in after a long history of launching projects that didn't make it very far. The conventional wisdom is that it takes years to build a successful business, but in this episode we discuss why that wasn't the case with Dawson's business Logojoy.


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Courtland Allen 0h 0m 8s

What's up everyone, this is Courtland from IndieHackers.com where I talk to founders of profitable internet businesses; with the goal of hearing about their stories and what goes on behind the scenes so that the rest of us can learn from their successes and their failures.

Today I'm talking to Dawson Whitfield, the creator of Logojoy. If that name sounds familiar it might be because I talked to Dawson last year for IndieHackers.com and his interview was one of the most popular that I've ever done. I think it hit a hundred thousand page views in it's first twenty four hours on the site.

There's a lot of talk about how success never really happens overnight and how it's always years in the making and I don't think Dawson is necessarily an exception to that rule. However, Logojoy, the product Dawson built really did take off the second it was exposed to the public and I think it's fun to hear him analyze why that happened, and tell the story behind it, so here we are one year later... Dawson, how's it going?

Dawson Whitfield 0h 0m 56s

Hey! It's going well, thanks for having me.

Courtland Allen 0h 0m 59s

Yeah! Thanks for coming on, last year when you were on Indie Hackers your story hit the front page of Hacker News and it was number one for that entire day but it ended up turning into a little bit of a scandal... do you remember?

Because what happened was that you had just launched Logojoy on Product Hunt, I think a week before doing your interview for Indie Hackers, and you made something like $7,000 in that first week so I extrapolated to say "oh, Logojoy is making $15,000/month." which is actually a pretty conservative estimate. I could've said $28,000 but people on Hacker News still got super upset about it and accused me of misrepresenting things, so it was kind of a mess.

A few months later in March, I get an email from you out of the blue saying "Hey Courtland, how's it going? Would you mind updating my revenue on the site? I'm at $70,000/month now." So your growth ended up proving the haters wrong but more than anything I was just floored by how fast you grew.

Dawson Whitfield 0h 1m 47s

Yeah, it was quite a roller coaster. I appreciate you taking the blame for that but I think it was actually me who extrapolated it and misrepresented it to you.

Courtland Allen 0h 1m 57s

Haha, I barely remember all the details but I do know that it turned out okay in the end.

So when we ended up doing the interview, you described Logojoy to me as an online logo creator that uses machine learning to make it feel like you're working with a real designer...is that still an accurate description of Logojoy today, a year later?

Dawson Whitfield 0h 2m 16s

It absolutely is. The one thing that's changing is that we're starting to expand our horizons and we're looking to really make Logojoy into a product that can design anything...so a logo, business cards, or a restaurant's menu. We really want to bring our technology to every kind of design.

Courtland Allen 0h 2m 37s

That sounds crazy ambitious.

Dawson Whitfield 0h 2m 39s

Yeah, it's a really hard problem to solve. The hardest thing about it is a lot of companies are sort of taking Photoshop, simplifying it, and putting it online, combining it with beautiful templates and all that. Which is a great product for a lot of people but we want to differentiate in saying "we're not going to try to make you a designer, we want to be your designer." and that's where the real challenges come in.

Courtland Allen 0h 3m 8s

You're going to do all the hard work for people and let them have the easy job of clicking the design that works huh?

Dawson Whitfield 0h 3m 14s

Exactly, one of our customers said it was kind of like watching TV, it was just so effortless and you ended up spending so much time just playing around that you ended up finding a logo that you loved, but we think you can find really any kind of design that you'd love.

Courtland Allen 0h 3m 34s

Cool! So let's go back to the beginning of Logojoy, how did you come up with the original idea for an A.I. powered logo maker?

Dawson Whitfield 0h 3m 41s

So, I've been a designer my entire life, about thirteen or fourteen years, doing it somewhat professionally. A lot of that time was spent doing logos for clients, so last summer I was doing a logo for a client and the whole process probably takes about three weeks. The client must have spent about $3,000 and really at the end of the day I felt like a glorified font picker, and it was frustrating for me because here I am, I've invested my life into being the best designer that I can, and I truly feel like I'm just getting in the way when I'm doing this work with these clients.

It really killed me, so I went out looking for a product that made it easy for entrepreneurs to get a nice looking logo. Didn't find any, so I decided to build it.

Courtland Allen 0h 4m 36s

It reminds me of that, I don't know if you've seen that comic by, I think it was the Oatmeal, where it's a designer making a website for someone and they keep second guessing every decision that the designer makes, and by the end of the whole process it's the ugliest website in the world. The designer is so embarrassed to have made it, haha.

Dawson Whitfield 0h 4m 52s

It's funny that you say that, it's really at the core of what we're doing, a lot of our customers love the perfect amount of control that they have over the process. It's a fine balance of we want to be able to give those smart suggestions and things like that for their design, but they still want to feel like they're somewhat in control so they can tell us to show them different fonts or different colors or anything like that, so it's really about finding the perfect balance of how much control we actually give the user.

Courtland Allen 0h 5m 19s

So when you first came up with the idea, did you have any inkling that it could become so big? What were your goals like?

Dawson Whitfield 0h 5m 25s

It's funny, so I don't know if you know this but my friends used to make fun of me because every month I had a new side project, and I'd always get super amped up about them. Then two weeks would go by, then I was done with it and ready to move onto the next.

With Logojoy, I could tell this is the one. It was just sort of that I had when I was building it that, that excitement lasted more than two weeks, it was such excitement that I would wake up and jump out of bed. I literally could not wait to go sit down and start working on it. I just sort of had that feeling, it was like this is what I was meant to do. this is perfect, before I even launched.

Courtland Allen 0h 6m 15s

What gave you that feeling? I imagine there were other tools out there at the time that helped people automate their designs or at the very least some templates and logo builders, so why were you so confident and so excited about what you were doing?

Dawson Whitfield 0h 6m 27s

You're right, there were a lot of people doing it and there still are. I think the biggest one was that at the time I had such a profound knowledge of the domain. I knew that the solution that I... it's like, I didn't even have to do user testing. My project before this was like an HR tool that helped people build employee handbooks... I had no clue what the hell that space was all about, so I'd do research and I'd be like "oh yeah, there's a market for this employee handbook builder and people spend a lot of money in the industry." but that didn't really get me going.

With Logojoy, I had been a designer for twelve years and I saw the product, and imagine my past clients using it, I can truly imagine myself using it. So I think that's what it was, it was just that intense domain expertise that I knew this was something that was needed.

Courtland Allen 0h 7m 32s

That's fascinating because it strikes me that there are probably thousands, or possibly millions or designers who work with clients and get annoyed at all the back and forth just like you did, but probably very few of them come up with an idea to make a product to solve it. Especially not an idea involving A.I. and machine learning so why do you think things were different with you?

Dawson Whitfield 0h 7m 53s

Well, I've always been a developer as well. I knew how to build it and I could build it, which was pretty exciting. Being able the actually build your product is just so invigorating that it fuels you. That's probably the biggest one, I don't know, I think just general ambition. I think it's just my personality, I love to build products, right? And if I can build a product that does a better job than I would but for a million more people, I'm going to build that product.

Courtland Allen 0h 8m 33s

I think that's one of the exciting things about being a founder today, because even though so many people are online and so many people can code, very few people are actually building stuff, you know... There's people working every job under the sun but very few are thinking "how can I improve this job or make it better?" so if you want to get into it, there's a lot of low hanging fruit and a lot of ideas that you would think someone has done but they haven't done, or they've done a very crappy job at it and if you're dedicated to it you can improve it, so it's a pretty good time to start something new.

Dawson Whitfield 0h 8m 58s

It's crazy, you look at a space like the logo maker space, logos have been around for a long time. People have been making logos for a very long time. Rationally, you would think "If somebody could have done it by now... someone would have done it by now." right? If someone could have made a really good logo maker, it would have been done already so there's no point of even trying. But yeah, just by caring so much... people underestimate how powerful that is. Just caring a hundred times more than the incumbents.

Courtland Allen 0h 9m 35s

And what did you think you cared the most about? Was it solving the problem, or making your own life easier, or making life easier for all of designers, or starting a successful startup? What was your primary driver?

Dawson Whitfield 0h 9m 47s

It's kind of superficial, but just building a slick product. I actually had in my notes, like what I want in the future and one of the top ones was I just want a slick product that I'm proud to show my friends, and makes enough money for me to survive on. I think that's what really motivated me the most in the early days was just making a really fricken cool product.

Courtland Allen 0h 10m 15s

That's a pretty good motivation, it sounds like you're a natural builder of things who enjoys building things for their own sake, at which point you want to take pride in your work. Then the question of how you get out of bed every day is easily answered because you're excited to build the thing that you're building, it's kind of it's own reward.

Dawson Whitfield 0h 10m 31s

Absolutely, and you spend hours refining the easing and transition haha.

Courtland Allen 0h 10m 40s

I was talking to one of my designer friends this guy, Tobias van Schneider, a few weeks ago on the podcast and we were talking about the difference between founders with a developer background and founders with a designer background. I think it's funny because as a designer you're kind of a perfectionist about the design, so it kind of slows you down in some parts because you don't want to release something you'd be embarrassed about.

Dawson Whitfield 0h 11m 0s

Yeah, I think there's another little mindset thing there, most developers I know care about cool things that are possible, little things to save time talking with the server and things like that. I think designers have a higher tendency to think about actually solving problems, empathizing with the user and thinking about how to design a product that solves the user's problem.

Whereas a lot of developers I know are like "oh yeah, we could use this cool technology in this way." and they don't really connect that with the actual problem that they should be trying to solve.

Courtland Allen 0h 11m 51s

Yeah, I think it's pretty typical as a developer to be much further removed from the level at which customers are expressing what they want. Especially if you're a back end engineer you might spend your entire career working on these systems that no customer will ever see, or touch, or know that it even exists. On one hand, these systems enable customers to get what they want, but on the other it's so indirect that you don't speak the same language that users are speaking.

Dawson Whitfield 0h 12m 16s

Yeah. A lot of the times some designers will wonder while actually designing products, they'll forget the twenty different "what ifs" that a developer will catch.

Courtland Allen 0h 12m 27s

It goes both ways. So I think, also there's something kind of scary for designers about a future in which A.I. can do their job, or some large percentage of their job. I'm sure it's scary for everyone, to be honest. The defualt response is denial, people say "oh that's impossible, maybe A.I. can do some things but it can't do these other things over here." meanwhile the things A.I. can't do are slowly shrinking in scope every year.

Ten years ago designers were probably like "A.I. can never make a good looking logo" and then today when they see Logojoy they'd be like "Okay, it can make a decent looking logo but it can't do all the custom details that I can" and I don't know what things are going to look like fifteen to twenty years from now, but I could see that being one reason why there weren't so many designers lining up to build an A.I. logo maker, because if you're kind of in denial about it and afraid of it, you're not going to do it.

Dawson Whitfield 0h 13m 13s

It's like a horse making a car, yeah haha. As a designer it hits really close to home for me. I don't think A.I. will steal designer's jobs, I think designers will always continue to evolve. You look back ten years, like you said, if you ask somebody to build a website you needed to hire a designer and developer. Now-a-days you just go on WordPress, or Wix, or Weebly, or whatever. I think designers will always evolve, maybe in ten years we'll need designers to design virtual worlds or A.R. stuff, so I think there will be a lot of evolution there.

I think the biggest fear is that we are basically making the industry look bad, so we're reducing the perceived value of design because we're saying "oh you can get it for free or for $65." and to that I say it doesn't necessarily matter. All we should be caring about is what the customer wants, what the small business owner wants, and if we can help them get off the ground faster with a logo that they love, for a tenth the price, then that's a good world. Then it's up to you to think about how you can provide more value.

Courtland Allen 0h 14m 31s

Yeah, exactly. It's kind of like being a newspaper editor in the 90's when the internet comes out and saying "oh we shouldn't go online." This is the inevitable force of progress and either you accept it, and try to provide more value in a better or new way, or you rail against it and eventually become irrelevant. Maybe one of the lessons here, if you're looking to come up with a business idea is that, if everybody in your industry is afraid of something or in denial about it, maybe that's a good place to look for creative new ideas.

So back to the story of the founding of Logojoy, you're super excited about it, you've got this new idea, you're waking up every day excited to work, and you're not really talking to anybody or validating your idea... what were you doing, besides just building, was it just nothing but building, and how long did it take you to get the product out?

Dawson Whitfield 0h 15m 20s

Yeah, it was literally just building haha. That's the other nice thing about doing something you have domain expertise in is that you can just build. It took two and half months, from idea to launch. Basically two and a half months of pure coding and design.

Courtland Allen 0h 15m 38s

I think a lot of people fall into this trap of not talking to anybody and not doing any research, and also not having any real domain expertise, so they build something for two or six months, and it doesn't get any traction. In addition to your domain expertise, were you a fan of any particular startup philosophy? A lot of people swear by Eric Ries's book, The Lean Startup, a lot of people swear by Paul Graham's essays, is there anything that you subscribe to?

Dawson Whitfield 0h 16m 3s

Anything I subscribe to? I don't know which of my mantras are also mantras of the startup world... I mean, one thing I did do, it wasn't really talking to users but I would often, well I did do beta testing with my friends and I would get some feedback there.

One thing I did was I would do a lot of reading online, I would go to design agency websites and see how they talked about their services, and like how they presented their logos, and tried to mimic things like that. One of the big things that we did was that we didn't do watermarks over our logo, we showed our logos with a lot of contrast, a lot of white space around them, and some things like that, so I did do a lot of things like that. I just looked at what the best people in the industry were doing, not the best logo makers but like, you know, actually one thing is the whole mantra of think about the job that your customers are hiring you to solve, so for us, the job our users were hiring us to solve was building them a beautiful logo. So I looked at not other logo makers, because I thought they were all crap, but I looked at who people were hiring right now to get the best logo that they can, and those are the top ten agencies in the world, and I looked at how they presented their logos, and how they communicated with their clients, and things like that.

I sort of mimicked the pinnacle of the best way you could do it, so I tried to mimic that as closely as I could. I think that really worked out well.

Courland Allen 0h 17m 47s

That's such a good way to go about it, to recognize it's not only about the product that you're building and trying to make the best logo maker, but to understand what problem your clients have, and what thing they really want, what do they want, and what do they desire, and I think it's a hard lesson for people to learn. I knew it took me a very long time to learn that lesson. Where do you think you learned that lesson, if not entirely from your job as a designer and working with clients, is there any other thing that influenced you to kind of teach you to think that way?

Dawson Whitfield 0h 18m 16s

Honestly, just building and testing out a lot of products. One old side project that took up two years of my life, same kind of thing as Logojoy, like ten hour days and it just did not have any legs, and I only realized two years into it. That was a really big learning curve. After that I was like okay, I'm going to make sure that I am solving a need that people currently hire other people to do, yourself.

Courtland Allen 0h 18m 49s

What was the product?

Dawson Whitfield 0h 18m 50s

It was called Wiseries, and it was an online marketplace for career advice, so we connected students and recent grads with people doing their dream jobs.

Courtland Allen 0h 19m 0s

Okay, that makes a lot of sense. Seems like something that people might want.

Dawson Whitfield 0h 19m 3s

Yeah that's what I thought!

Courtland Allen 0h 19m 5s

Haha, I like talking about failure stories because everyone who's succeeded has done like at least a handful of things that didn't go over very well, and I think it's interesting to dive into it because then all of us learn what it is that you learned to get you to the point where you could create something that succeeded really well.

Dawson Whitfield 0h 19m 21s

I love postmortems!

Courtland Allen 0h 19m 22s

Yeah, postmortems are great! Why don't we dive into a little bit more detail on that. What was the process like of you figuring out that it wasn't going to work?

Dawson Whitfield 0h 19m 31s

So I liken it to, so I built the product thinking to myself, and I was marketing it myself, so it was during when we were marketing it then I realized it wasn't going to work. I liken it to running with a parachute behind you, this parachute is like the non-product market fit parachute, then you can take it off when you have product market fit and you can actually run.

Courtland Allen 0h 19m 55s

Haha, it's kind of hard to tell that sometimes though.

Dawson Whitfield 0h 19m 57s

I mean it was a slow realization, but it was pretty obvious, people just didn't stick around. Then there was a moment where I was like this isn't working, the business model... people didn't want to pay for it, that's probably the biggest one, people didn't want to pay for it.

Courtland Allen 0h 20m 17s

Yeah that sounds rough. What kinds of things did you try to get people to pay for it, or was it a situation where you tried one thing and it didn't work out so you kind of just cut your losses?

Dawson Whitfield 0h 20m 26s

No, we tried everything. So, on the checkout page I added all these great benefits of getting a mentorship. I tried to be like the matchmaker, so I would send out a hundred emails a day saying "Hey, John you should talk to Sarah" and vice-versa... I did a lot of that, it's kind of blurry for me but I did a lot of wild things for that.

Courtland Allen 0h 20m 56s

That's such a tough problem to solve and I haven't seen very many matchmaking services, with the exception of dating apps, really take off in a big way. I think both people who are being matched have to be in the right place and point in their lives to be matched for whatever purpose, and you really need to find something where you can match people frequently, instead of just once and then their done, so it's really just a tough problem to solve and to get people to pay for.

Dawson Whitfield 0h 21m 18s

Yeah, it was really hard. The hardest thing was that all the mentorship sessions were over the phone. Oh! You know when was a really bad time? When Google launched Helpouts and I was like cool, this was when I was like halfway through, they're validating the industry, this is good! Then Google shut down Helpouts and Helpouts was doing the same thing that I was doing and I was like... oh, well... this might be a sign. So that was a bad one.

Courtland Allen 0h 21m 52s

That's rough stuff, but here you are, years later and you find yourself working on yet another project that you're super excited about, and you're spending ten hours a day on it and you're excited and optimistic about the launch even though it's not clear that things are going to work out in the end, and of course now we know in hindsight that it did work out but tell us about the weeks leading up to launch, and how you got ready to unveil your project to the world.

Dawson Whitfield 0h 22m 12s

So I did a lot of beta testing, I had a pretty good inkling that this was going to be a success, I was hoping, out of the gates. I had a Facebook group with my friends doing beta testing, but I really didn't focus too much on the marketing plan. In all my other products, I've really focused on the marketing plan and I've spent like the last two weeks with the product getting ready to launch, working on how to launch on day one, and I've learned you should never have a launch date, it should always be a slow roll-out. I had Chris Macena post it on this forum on his website, for people to ask him to post stuff on Product Hunt for them, so I did that and I was lucky enough to have him post it for me. Yeah, the weeks were really spent just building and refining the design of it, and our heads down coding. Almost no marketing.

Courtland Allen 0h 23m 19s

Why do you think this slow roll-out method worked better for you, how did you go from doing these big marketing pushes to this totally new approach?

Dawson Whitfield 0h 23m 27s

Because the marketing pushes have never worked, and it's always a let down. To launch your product and have a let down on the first day can be devastating, and can really just deflate you, so I've learned to have almost no expectations when I launch. You can do that by launching when the product is like okay.

Once you have no expectations when you launch, then you haven't exhausted all of your enthusiasm before you launch, so this way when you launch when it's okay you still have all of this fire inside of you to carry it on when it's actually out there, which is 99.9% of the work.

Courtland Allen 0h 24m 11s

Yeah, there's so many guides online that are like "A hundred checklist items that you need to do before you launch" and you read those and they're so overwhelming, there's no way I'm going to do all of this, it sounds exhausting, I'm probably going to miss half of it... I can't imagine doing all those things and then having the launch just flop and still wanting to keep going.

Dawson Whitfield 0h 24m 32s

Yep, exactly.

Courtland Allen 0h 24m 33s

I think people really underestimate the psychological aspect of building a product and they don't really take it into account when they're doing their planning. If you set yourself up for these huge failures, where your expectations are massive and it all hinges on one moment of time, then when things don't go well you're going to quit, and if you quit you won't win.

Dawson Whitfield 0h 24m 50s

Yeah, also I found that just focusing on marketing a product after you've launched it is also helpful, because you're a lot more inspired and excited to market something that's actually out there. I love being able to have an idea, for example a marketing idea, and being able to do it that same day. When you're thinking about marketing ideas before you launch, first of all you're taking time away from building it, second of all, it's not as exciting and you probably won't be as motivated to do it if you haven't launched yet.

Courtland Allen 0h 25m 27s

Yeah, not at all. I think another thing worth mentioning is even if you do have a big launch that goes really well, the weeks after that are most of the time, not that great. They're kind of discouraging. I think for you, you ended up growing a ton but I remember when I launched Indie Hackers, I kind of had no expectations, I'll launch it when it's done, and I think on a Wednesday I was like "You know what, I'm launching tomorrow." and I emailed a few people to let them know, and it went really well.

Then the next three weeks I think, the traffic was lower every single day then it had been the day before. I had no idea where the bottom was going to be, I just thought it was going to go all the way down to zero, it was super stressful. I kind of regretted doing this huge launch out of the gate, I wished that I had slowly rolled it out so at least have the happiness of seeing the traffic go up instead of down every day.

Dawson Whitfield 0h 26m 12s

Yeah, absolutely.

Courtland Allen 0h 26m 14s

So let's fast forward back to the present, you launch Logojoy, make $7,000 in it's first week. Then you do an Indie Hackers interview, that blows up. You email me a few months later in March and tell me Logojoy is doing $70,000/month in revenue... Where is Logojoy today, how big is it, and how much revenue are you guys generating?

Dawson Whitfield 0h 26m 33s

Yeah, by the way it's almost been a year.

Courtland Allen 0h 26m 37s

Yeah, pretty close!

Dawson Whitfield 0h 26m 39s

So yeah, it's been quite the roller coaster. We are up to twenty four employees. We're doing just over $300,000/month, it's Canadian. It's been quite exciting, lot's of growth. Our first summer, we realized the seasonality of business, that was terrifying. We had a couple months in the summer where we had down months, I was like oh shit, this is it, we're going down.

Courtland Allen 0h 27m 17s

You wouldn't think that a logo maker would be really that seasonal, what happens in the summer?

Dawson Whitfield 0h 27m 24s

I had a couple conversations with some industry veterans, and they sort of confirmed this, businesses just start less in the summer, I guess. People are off on vacations and stuff like that, but we made it through and we moved into our own office here in Toronto.

Courtland Allen 0h 27m 45s

Yeah, I haven't really followed up with you since we last talked so I had no idea that you were at twenty four employees. When we did our Indie Hackers interview it was just you by yourself right, so you've added all of those people since then?

Dawson Whitfield 0h 27m 57s

Yeah, it was just me.

Courtland Allen 0h 28m 0s

It's crazy, the whole idea of just being in this situation where you're a one man shop, and you can grow to be pretty much anything that you want. You can stay indie and small, and treat this as a one man business or you can try to expand your team as fast as possible. You've got funding decisions too, you could bootstrap or raise money from outsiders. What was going through your head when you saw things starting to explode early on, and how did you decide which path you were going to follow?

Dawson Whitfield 0h 28m 26s

What's funny is that there was no conscious decision, and I realized this afterwards. I just sort of, by default, was like alright sweet I can hire someone now, and I can get someone to help me market it, and get someone to help develop it and do support. Only until we were at like fifteen people was I like "Oh, shit you know what..." not that I would ever want to I was like, "I could've just stayed indie and be making you know, whatever it was."

For me, I don't want to live life to achieve good success... I want to change the world. I want to make something that everyone in the world knows about, and every entrepreneur uses. For me there was no conscious decision to stay indie or to grow it, it was just growing, obviously. With whether to raise money or to stay bootstrapped, that was a very hot topic, and even with investors, I had very prominent advisers be physically angry at me for like "Why are you raising money, why don't you just bootstrap?" because we don't have recurring revenue and we wanted to grow pretty aggressively along with our revenue, we needed money in the bank as padding, for when December rolls around or when the summer rolls around. I knew we needed to raise money, we ended up raising $900k to dive into a little bit but mostly just to have it in the bank.

Courtland Allen 0h 30m 8s

So tell me about that fundraising process because it's not something that I really talk about very often on the podcast, and I think a lot of people who are listening would be curious to hear what it's even like to do that, like how do you raise money from investors?

Dawson Whitfield 0h 30m 19s

It's brutal, haha, it sucks, I mean I guess some people like it but I imagine most Indie Hackers would not like it, I don't like it... well I'd probably like it now, but when I had to do it, I just wanted to be building product. It's demoralizing, because you think your business... I was super pumped we were doing at the time, I don't know, whatever it was, $100k/month, but I would tell investors that and they're like "Yeah, but it's not recurring." and I was like, well shit.

So it's super demoralizing, what was really important was a big learning curve for me is... I didn't know why we needed it, to investors that's a big red flag if you're not deliberate about every single major business decision, that's a sign of an inexperienced founder. That was a big one for me, I had to really think thoroughly on why we wanted to raise money, and why we didn't want to bootstrap, and that is as I said was because we need that buffer and we want to grow aggressively with our revenues.

Courtland Allen 0h 31m 36s

How many investors did you talk to and how many "no's" did you have to get before you started getting some "yes's"?

Dawson Whitfield 0h 31m 41s

Man I thought, I was like, we have revenue, we have product market fit, everyone else got "no's", we're going to get "yes's", I probably talked to about forty, forty-five investors. Eventually about ten said yes.

Courtland Allen 0h 32m 2s

Okay, that's not too bad. That's not like a disaster story. I've heard hundreds sometimes in the past.

Dawson Whitfield 0h 32m 7s

Yeah, it wasn't that bad, but I was frustrated as hell. Every time an investor said no to me, I'm like "What the hell are you thinking??" It sounds bad but I was like, I'm going to prove you so wrong! Eventually once you get enough "no's" you're like, it might not work with his or her portfolio, or I don't know, something like that.

Courtland Allen 0h 32m 31s

Yeah, I say that I've heard worse stories in the past but honestly if you get told "no" even five or ten times, that can be pretty devastating.

Dawson Whitfield 0h 32m 38s

It's super crushing, yeah, it's an absolute roller coaster.

Courtland Allen 0h 32m 42s

I like what you said about the investors really wanting to see that you're not just making decisions haphazardly, that you're very deliberate and confident, and that you're planning, and you have foresight to predict what's coming up and make decisions accordingly. Otherwise they'll think you're an inexperienced founder, and what's crazy is that if you're growing a company as fast as you did, you probably feel some degree of inexperience no matter what, like you're riding this big wave and one hand, of course you want do things to push things forward and make the wave bigger, but on the other... you don't want to fuck things up. Is that something you've ever worried about or been afraid of?

Dawson Whitfield 0h 33m 15s

No I'm not afraid of it... well maybe I am, but I think one of the biggest things that I've learned is just embracing the fact that this is a super exciting journey that you're on. You're not going to know everything. You are new to this. One of the most profound things, somebody told me, the most growth that you'll ever experience comes from pain.

Investors say "No, you're business is not going work for these three reasons." that is painful, but it means the next time you go into an investor meeting you're going to be able to say "My business will not die, because of these three reasons." and you can counter before they even say it.

I think emotionally just being aware that it's going to be a storm, it's going to be chaotic, everyone goes through it, and the most exciting thing for me is whenever I experience some sort of major setback I imagine myself a year from now, and I say "Holy crap, I'm going to be so much stronger, so much more experienced, and I'm going to be a much better person because of these challenges I'm going through today." because I know I will get through them.

Courtland Allen 0h 34m 40s

What are some of the things you can look back on to the Dawson of a year ago, and say, I've grown as a person or as a founder in these ways?

Dawson Whitfield 0h 34m 49s

So one of the biggest ones, again, when talking to investors, is how you present yourself, how quickly you talk. If you don't know the answer to a question, how you are straight up about that and don't fumble your words. Even when you're talking to potential employees or actual employees, is just being very aware of how you present yourself and how that should change depending on the context.

For example, when you're chatting with investors it's really important to talk slowly and to seem a little more like you have all the answers, you are confident in everything you say, you are sure of. Whereas if you are chatting with a team member, it's actually better not to pretend like you know everything. It's important to talk with a little more doubt in your voice, so they don't take your word as the prescriptive answer, so they're not afraid to challenge you. So I think that's the biggest one is just how you present yourself in different contexts.

Courtland Allen 0h 36m 10s

And what about pain, because you talked about growing from pain. Part of that was the downturn in the summer, and part of that getting told "no" by investors, but are their any other painful things and experiences that you've learned from or any nerve racking decisions that you've had to make running Logojoy?

Dawson Whitfield 0h 36m 27s

Yeah, there was one that happened the other day. I've since brought on a co-founder, a good friend of mine, Raj, and this is at the end of the summer when we were going through the financials and he trusts to have a very good grip on the financials, obviously, it's critically important. There was a moment where we basically sat down with the spreadsheet in front of us, and he said this is not right, this is not right, this is not right. We were in a much worse position then I thought we were, financially. I felt like a complete failure. I felt like I had not done one of my main jobs, he was counting on me to have things covered and I just dropped ball. That was a major one, that I've learned and I think from there, I think one of the biggest learnings from that is, if you take on a job you better be damned sure you're going to be able to do it well. When I say well, I always think if I were to hire someone to do this job for me, how would I expect them to do it, how well would I expect them to do it? And I do it that well, or better. That was sort of a big pain and a big learning curve for me.

Courtland Allen 0h 37m 51s

You know, I think one of the helpful lessons to come out of that as well, that's kind of ancillary, but it's just how helpful it can be to have a co-founder, because it doesn't sound like this is a mistake you were going to have caught by yourself. Yet regardless of what happened, you kind of indirectly fixed it in advance by being prescient enough to say, hey, even though I'm running this super booming business by myself I should bring in a co-founder to help me out, and I don't think very many people would have made that decision.

Dawson Whitfield 0h 38m 14s

Absolutely, it's all about surrounding yourself with people... co-founders, or general team members, surrounding yourself with people who really care, putting a structure in place that makes them care. Whether it's equity, or giving them a voice, or putting a lot of trust in them... surrounding yourself with people that really care.

Courtland Allen 0h 38m 43s

So you've got twenty-three or twenty-four people working with you on Logojoy right now, and it's funny that when you describe how you made that decision about how fast you wanted to grow and what type of company you wanted to be, that almost wasn't even a decision for you. You just kind of automatically knew that what you wanted to do was hire people and grow as fast as you could. I know a lot of people who would have made the exact opposite decision, the last thing they want to do is have to manage people. I think it's especially common among people who are builders of things, because their skill, and their desire, and their expertise lies with building things, and they don't really have management experience.

So I'm curious what you're management experience looked like and why you were so confident in hiring people, and the kinds of things that you've learned since you started growing your company.

Dawson Whitfield 0h 39m 23s

What's brutal for me was like three or four months, for a lot of people I imagine it's like a year or two, that sort of transition period from building a product to building a company... That's really hard because you can't do both well, so for me there was like three or four months where I was doing two things, not very well, so that sucked.

I'm the kind of person, and I think a lot of entrepreneurs are like this, my main driver is not writing code, it's not designing... it's fulfilling the potential I see in myself, right? I don't see myself doing that by staying in sketch and designing checkouts, as much fun as that is, I just don't see it. During this phase, that's sort of the silver lining that I saw is, the transition sucks, acknowledge that and prepare for it but on the other side is a person, you, who is much closer to their life goal of, for me it was fulfilling my potential in myself, and I think for a lot of people being able to look back a year ago and look at how much you have grown as a person, is incredibly satisfying.

Courtland Allen 0h 40m 53s

Yeah, that's one of my favorite feelings as well, to just be able to look back at your old self and think "Jeez, what was I thinking?" then to know that, that feeling means that you've come a long way.

Anyway, we've covered some more negative pain points that you've gone through and learning experiences, but let's shift gears to some more positive stuff. If you had to say, what would be some things that are most responsible for Logojoy being so successful? Why do you think this company has worked out so well?

Dawson Whitfield 0h 41m 17s

I think I just sort of got lucky... the right product, the right time. The people in the company are just so amazing, they all care so much. We all see ourselves as part of this all star team, and we're taking on the world, and there's so much potential in front of us, and we're all gassed up and ready to go get it. Instilling that culture of, let's go get it in the company has been a big one.

With the product itself I think we've got a good balance of really caring about the design, but not too much that we don't release a feature because it doesn't look that great. There's a balance there that I've had to sacrifice on design on, so it's that balance of, yes we really care about the design but we also want to be quick and release features, and we want to allow one developer to build an entire feature because that will be a lot quicker than having him work with another developer and a designer and things like that. So yeah, I think probably the biggest thing that is responsible for our success is releasing features quickly, not needing to analyze everything before we test or do this big QA thing, we just sort of get it out there and see.

Courtland Allen 0h 42m 52s

One thing I find fascinating is that even at the beginning you guys were in a pretty crowded market with a ton of competitors, and they might not have been doing exactly what you guys were doing and they definitely weren't doing as good of a job but by now you've got probably a lot scarier competitors. I mean, you've got to have at least a few companies who've just outright copied exactly what you've done, and are now competing against you. Despite all that, you guys are still killing it. You're growing in head count, your revenue is much higher than it was earlier in the year, so I have to ask, do you think about the competition at all and is it something that worries you?

Dawson Whitfield 0h 43m 23s

We've had at least three people exactly copy our code and put it up on another domain, that are still running today actually. Thankfully that's no longer possible... but why are we still winning over the competitors? I mean, the good news is that competitors will rarely kill you at this scale, even if you have major competitors people will still end up clicking on your ad before their's, and if you're good enough at converting them you can still own that customer. There's a lot of customers to go around right now. I don't really look at any other logo makers, I mean when there's a new one I'll check it out just to make sure it's just as not as good as the other ones. There have been some pretty good ones that have launched in the last year, but again the scale is so small that worrying about it is a waste of energy, so I'm not really worried about our competition.

When I look at "competition" I look at, basically the competition in where we want to go, so when I imagine Logojoy in two years... who is our competition at that size, and I look at them. Again, that's looking at design agencies, when hopefully we'll be competing with them in two years. That's looking at products, as I mentioned, we want to move into all other kinds of design, so looking at products that offer all other kinds of design. Looking at them and what that landscape looks like, so it's really sort of like looking at our competitors two years from now and seeing what they're doing.

Courtland Allen 0h 45m 5s

Yeah, I think that's a smart way to approach it, to always be looking forward to where you want to go, rather than worrying about who's catching up from behind you, because if you're always looking back and worried about that, then it really means you're not moving fast enough. By the time other people catch up to you, you should already be months or years ahead of where you were at that point.

Dawson Whitfield 0h 45m 22s

Yeah and I just wouldn't stress, whenever a new logo maker comes up on the team, people get spooked. They're like, oh shit a new logo maker, they're going to steal 20% of our business. That's never the case, never the case. People underestimate how many customers there are to go around. Maybe you're advertising on Facebook and the other competitors aren't advertising on Facebook. There are a lot of customers to go around.

Courtland Allen 0h 45m 47s

Exactly, your competitors don't have to die in order for your business to succeed in the vast majority of industries, and it's a shame more people don't realize this because people will get discouraged and not start a company just because they see that other people are doing similar things. On a related note, you mentioned Facebook ads and it makes me curious, how does Logojoy grow? I mean every business, at the top of their list the number one thing they want is more traffic, more users, more customers, more revenue, how do you guys get customers in the door at Logojoy?

Dawson Whitfield 0h 46m 14s

So our first like five months, our growth was 100% fueled, apart from Indie Hackers, by AdWords. We would spend $1.00 to acquire a customer and about four days later, we would get a $1.10 back from them, so that was our entire marketing plan for the first four or five months. That would not be scalable, the only reason we were able to hire people and move into an office and all that, was because of SEO. Now-a-days about 55% of our new users come from organic SEO, we've really pushed hard on that. Then just word of mouth is where we've seen the most natural organic growth up until now.

Courtland Allen 0h 47m 12s

I imagine for something like, logo makers, SEO's got to be super competitive because there can't be that many terms people are searching for to find you guys.

Dawson Whitfield 0h 47m 19s

Yes, basically logo maker haha

Courtland Allen 0h 47m 22s

Exactly, so what do you guys do to win that race?

Dawson Whitfield 0h 47m 26s

Thankfully Google is pretty smart, we go there without even trying and then once we were there we were like, oh my God this is hugely profitable... let's start trying. We have a great PR person, Melissa, we incentivize people to share us. I truly believe that social sharing does have an impact on SEO. We give out free logos if someone wants to review us. We work with some bloggers and some publicists to get our name out there.

Courtland Allen 0h 48m 14s

SEO is such a dark art, I mean nobody works for Google, nobody knows exactly how their algorithm works, so the best we can do is guess. Even if we hit on something that kind of works right now, who's to say it's going to work in a month from now or a year from now, so it's fun to talk to people like you who's businesses benefit so heavily from search engine optimization and traffic.

Dawson Whitfield 0h 48m 36s

Yeah, one thing I love is doing microsites. We have one called, how to make a logo, it was inspired by Crew, they had a micro site called, how much to make an app, which outlined how much it would cost to make an app, but we have one called, how to make a logo, and it's been super popular. It basically outlines every option there is to make a logo, and we have a couple other microsites in the works and those have been pretty beneficial.

Courtland Allen 0h 49m 9s

I think microsites and these side project marketing type things are so smart because not only do they help you on the search engine rankings, but they also help you provide value to your customers. I mean, you're literally making something that's helpful for them which is always a good thing to do, if nothing else you'll learn a lot from that experience.

The alternative, content marketing, is something that's not for everybody. Not everybody wants to be on a content treadmill, not everybody likes writing, so if you prefer coding and making products, and maybe that's what you're better at, then you can build a side project or a micro site that's geared towards bringing in traffic.

Dawson Whitfield 0h 49m 40s

Exactly, the thing is bloggers and publishers don't link to other blogs as much as they used to right? Ten years ago when you liked a blog post, one of the ways you would show that appreciation is by linking to them, now-a-days that happens a lot less. What's worthy of a mention in a blog post, that bar is going higher and higher and higher, and it's why micro sites are becoming more and more popular because a micro site is much more worthy of a link than a blog post.

Courtland Allen 0h 50m 30s

Yeah, if you're going to get on the top of Hacker News or Designer News or any of these sites, Product Hunt, then probably people are more likely to talk about a substitutive interactive micro site.

Dawson Whitfield 0h 50m 41s

Yeah, except for Indie Hackers.

Courtland Allen 0h 50m 44s

Haha, except for Indie Hackers it's all content, but luckily I don't write it all by hand, otherwise I would fall over dead.

So on a more personal note, I'm curious about how your life has changed in the past year, because you've suddenly gone from freelancing and working on these smaller projects, to being thrust into this role where you're running a company of twenty people... what does that do to a person, especially a person who's not necessarily excepting it? Are you stressed out all the time, are you loving life, or both?

Dawson Whitfield 0h 51m 12s

I'm loving life man. One thing I learned is that it's so easy to be stressed out all the time, if you don't deliberately get a grasp of your mindset, you're going down. You're going to get stressed out, you're going to be always frustrated, always irritable. One thing that has changed about me is that I'm really good at talking to myself, I'm really good at getting a grip on my emotions. So now if something really stressful happens, like we're slapped with a legal claim or something like that, my heart doesn't sink anymore, I don't get super stressed out. I say, alright, I've handled things even harder than this before, it's going to sound really bad at first but with these things they always sound better the next day so let's just stay cool.

That's one of the big things that's changed with me, I spend like an hour every night making sure I'm mentally okay. That's one big one, what else... One thing, you're a lot more humble. It's amazing, what happens to you overall is amazing. One of the best things is you are so much more confident, in a good way I think, it's not like you're super cocky because you're this big CEO or whatever. You're just a lot more comfortable in your own skin, like truly comfortable in your own skin. You stop caring what people think of you, so yeah, you're just like a lot more... it's just like a really healthy confidence that you feel like you always had in you, but now because you're in this pretty high position, that's enough for you and just because that's enough for you then your confidence is great.

Courtland Allen 0h 53m 28s

That's really awesome to hear, I especially like the point about if you dive into the deep end you're going to accumulate experiences that are hard and then when you run up against other hard things you really can say, I've been through worse. You really can say, oh yeah I can for sure survive this because I survived that other thing and that was twice as hard.

I think a lot of people listening in are just considering building a business online, or maybe they are looking for an idea, or they've taken a few steps without much success so far... what would be your advice for someone in that situation?

Dawson Whitfield 0h 53m 59s

One big one is, that was literally me exactly a year ago. A year ago today I was in my living room, had one month of rent left in my bank account, and I was just coding on this side project that I thought might be a thing. I think if I heard someone say that, I think I'd be a little more motivated to keep working on it, but yeah if I were to give one piece of advice it's just to know that it's fully possible for your side project to blow up. The most common thing is that takes years and years and years for something to even start showing any signs of traction, like Airbnb or something like that.

I think a much more exciting thing is that it's actually possible for you to launch something and then in a year, it'd be a big company and you're like, solid growth, and making a good amount of revenue, and really making a difference in the world, that's fully possible, which is really exciting to know. I think just be aware that it's fully possible and just keep building, keep building.

Courtland Allen 0h 55m 32s

Yeah, I mentioned this earlier but it's exciting to know we're living in a time where one person can accomplish so much, and it's wise to keep your expectations low and not put a ton of pressure on yourself, but if you're ambitious and you do the best that you can it's also motivational to know that you can build something that succeeds pretty quickly.

Anyway, thanks for coming on the show Dawson. It's been great having you, can you tell listeners where they can go to learn more about you personally and the things that you're up to at Logojoy?

Dawson Whitfield 0h 55m 57s

Yeah, you can go to my personal website DawsonWhitfield.com and Logojoy is at Logojoy.com

Courtland Allen 0h 56m 8s

Alright, thanks Dawson!

Dawson Whitfield 0h 56m 9s

Thanks so much!

Courtland Allen 0h 56m 10s

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Thanks for listening and I'll see you next time!

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