Drew Wilson of Plasso

Recently I sat down with Drew Wilson of Plasso where we discussed how successful businesses developed out of years of experimentation and cross-pollination. We also talked about some of the differences with bootstrapping versus raising an angel round through Drew’s experience on both sides.

Garrett Dimon: We’re here with Drew Wilson of Plasso. Drew, I’m going to let you go ahead and give the spiel about your background, your history, how you got to where you are right now, and a brief view about Plasso.

Drew Wilson: I started off as a child, like most people. When I was a kid I started doing art and crafts, and stuff like that, paintings. I was into that, and then that evolved into using Photoshop because my dad had to use it for work.

I was exposed to that super early on, version 2 of Photoshop, and over the years grew to love. I come up with concepts like design concepts in Photoshop. Made my first website in 1996, 20 years ago, and been building things on the web since then. I taught myself how to code like back-end code. In 2002, just out of necessity and didn’t know anybody else who did.

I wanted to see the stuff I was making in HTML. I just want to see that stuff like be real with the data base and all that jazz, even though I didn’t know any data base was at that time, taught myself that. From there moved into a bunch of developer stuff.

I never wanted to be a developer, I always thought it would be like always super nerdy and boring, but I ended up I really like doing it. It was great being forced myself to do that because now I could design, and code my stuff, and make products.

From a young age, I’ve always wanted to have a business there, do my own thing that kind of thing. Worked out good in that sense. Learned how to code, and learned how to design, and then spent my entire career building different little apps, product services, that kind of thing. Most recently Plasso, bada boom.

Recently, in the last year, gone full time on Plasso in the sense of not working on anything else, and raise money, and build a team around it, and taking it to the next level.

Garrett: That is, to me, one of the most interesting things with you is you’ve done so many different products and projects. Not just apps. Some of it is installed apps for the mac. A little bit of everything.

How did you juggle all of that, and how did you decide, and at what point did you know, “OK, I’m going to just completely focus on Plasso. I’m going to raise money. I’m going to settle into this and really swing for the fences”?

Drew: I had a threshold in my mind, not in specific number or anything like that, but… rewinding the clock back a bit, in 2010, I released a set of icons called Pictos. By doing that, I had no idea it would, but it made me a lot of money.

It gave me enough money to work on whatever I wanted to work on without having to do client work, which is what I had always done before that. I knew that the money that Pictos was making wouldn’t last, because there are only so many designers buying icons.

I wanted to find something that had its own legs and would work on its own without me trying to force it. I had come up with an idea that’s cool.

If I wasn’t getting much traction, I could spend all my time, try to force it, and try to get a bunch of traction, or I could just move on to something else and wait until I get something that’s got its own momentum.

That’s what I was trying to do. There are definitely other ways about going about building a business, but that’s just what I wanted to do.

I ended up finding that with Plasso. It had its own legs, and it was doing well on its own. It was making enough money for myself and then some.

I was like, “This is working out better than all the bajillion of other things I’ve tried. This thing is doing something different. I want to take it to the next level because of the fact that it was doing well on its own.”

Garrett: Looking back, do you think you would have come around to creating Plasso had you not gone through everything else you created? In a way, you were building things… A lot of your products served your own needs to sell your own stuff.

It seems, from the outside, at least, like Plasso was more of a product of your diversity of projects rather than its own little thing that just sprung up out of nowhere.

Drew: Plasso has a longer history than just the brand Plasso. My venture in e-commerce started off as a product called Quixly, which was… you could sell your digital goods super easily using PayPal or Google Wallet. That was launched in 2009. That was before Stripe was around.

I built that to sell my icons and, also, to try to make money off the platform. The business model wasn’t good, there.

It was old-school days. I was charging based on how much storage you use and all that jazz, which is so far and away, now, nobody does that [laughs], not even Amazon.

When Stripe came out I wanted to make a human interface with Stripe. It’s just something that… anybody could use Stripe because it was a developer tool only. I made another app that had a lot of the same functionality as Quixly but was focused around general payments and that was called Spacebox.

Again, I didn’t get the business model right there so that platform didn’t make… it didn’t make me money either. I came up with a new business model and then re-launched, recoded the whole thing, rebranded it as Plasso. With that new business model, things started working out and it started making money.

Plasso, itself, is a long time coming. I haven’t been working on Plasso, the brand or the specific feature set for all that long, but in the realm of e-commerce and selling things online, I’ve been working on it for years. Like you said, for me, it works out great because I could sell my own stuff. If the platform itself doesn’t do well, but yet my other things are doing slightly well, then I win. [laughs]

Garrett: Absolutely. That’s one of the things that so many people miss out on. Somebody will hear about Plasso and be like, “Wow, that’s so cool. He created Plasso.” Little do they see all of the iteration and other projects you did in the meantime that led you Plasso. It’s the whole 10-year overnight success type of thing.

To me, that’s just definitely one of the most interesting things because everybody’s got all their side projects and then they’ve got to make that decision like, “Well, I don’t know. What do I focus on? What should I do?” A lot of times it’s having multiple side projects that cross-pollinate and give you those ideas to create something bigger.

Drew: Totally.

Garrett: You’ve done all that and now with Plasso, you’ve raised money. Talk about that process and how it’s changed things now that you’re in a different place with Plasso.

Drew: The major difference after raising money is that there are eight of us now. Up until this point, every line of code, every pixel, every score email was just me and now, it’s a team. That changes things a lot from product perspective, from customer perspective, from everything, which is great. That’s the biggest difference.

Another difference is I have what’s called a runway where I have money in the bank that’s just waiting to be used versus it being… Where when you’re like bootstrapping until you get to the point where you’ve got tons of money in the bank… It’s always like a month-to-month you’re trying to figure out how can I budget on the super slim amount of money I’m making in order to grow it, that kind of thing.

Whereas, now, I have money that I can use to for… mostly, it’s important is to hire people. I couldn’t do that if I was bootstrapping, which is why I went to raise money because I bootstrapped all my career and now I wanted to do something differently. I wanted to raise money because in our industry that’s available to us and if you’re doing something cool, you can get super good terms when it comes to raising money.

For me, it was a no-brainer. I’m going to go raise money, I’m going to build a team around it, and go way faster than I could ever go by myself. Yeah, it’s a super different kind of company than somebody that’s been bootstrapped. I didn’t go raise money from any VCs or any kind of that. It’s all angel money. There is a pretty big difference there from companies that have raised money from VCs where they raise like a huge amount of money versus what I did.

Garrett: You may not have a frame of reference to compare but to what degree would you say the fact that you bootstrapped ahead of time gave you some leverage in raising money to where you could get better terms and put yourself in a better position than if you were just coming in with really hardly any traction or anything like that and just a solid idea?

Drew: If you were to put that on a scale of 0percent to 100 percent, it made 100 percent difference by having bootstraps for a variety of different reasons. On my perspective, on me personally, as the CEO, founder and all that jazz, it makes a world of difference, 1,000 percent difference, because of the fact that I’ve bootstrapped for so many years, and tried so many different ideas and failed, and lost all my savings many times over.

Sold all my furniture in my house multiple times. I know what it’s like to lose money, to have money, and how to hold on to money, that kind of thing. It’s a more serious endeavor for me. When I’m taking money, I feel like I’m taking someone’s money. I don’t feel like this is owed to me, or I have no risks.

I am really big on the entrepreneur taking all the risks themselves first, and then if something’s going good, then see if somebody else wants to come in, take a risk with you, and give you some money. If you don’t have that fire under you, I feel like you’ll probably be irresponsible with your money. That’s on my side. Then I’m suddenly forgetting what the original question was.

Garrett: It’s just how much easier it was, having bootstrapped already, and having some leverage going into raising money.

Drew: Going into it, the fact that I was making money made it so I could raise money, because it’s a SaaS product. When I started raising money in February, there was a bunch of articles coming out about how the VC climate has totally changed, and now it’s impossible to get money. Raise money now, or forever hold your peace, that kind of crap.

I was like, “Great. Now that I’m going to raise money, this starts happening.” For sure, 100 percent, I don’t think I’d be able to raise any money unless I was making money. There’s two. From my perspective, this is how it is. If you’re going to raise money for a company that’s a B2B, or a SaaS, or something like that, you have to be making money if you want someone else to give you money, because that’s the only time you’re going to get data on if this is going to work.

You’re working with a smaller customer base than a Snapchat or some consumer app product. Then you have a huge potential customer base. In those cases, most people come in and raise money on an idea. “Hey, I’ve got this idea for this anyway. We have this minimum viable product about how this is just our friends on it. We haven’t obviously launched an app store, nor are we going to until we get your money, and then build the thing for reals.”

That’s how most of those deals go. In those cases, you don’t necessarily need to be making money, but if you’re going to be doing a SaaS, or a B2B, or something like that, you’ve definitely got to…

Garrett: Have some traction.

Drew: Yeah. You have to have some traction. In the case of SaaS, traction means sales and revenue.

Garrett: Looking back, do you feel like you raised money at about the right time? A little late, a little early?

Drew: Looking at the charts and stuff, had I raised the year prior, that would have been better, but honestly, just the way stuff was for me personally, I think I raised at the right time.

Garrett: Right on. Without getting off on a tangent too much, there’s always interesting stories once people get the .com for their domain. I have a feeling there probably is. Is that true? Can you give that a quick overview, of how that went down?

Can you share any interesting details behind that, for anybody else who’s getting started, and feel like they need the .com? A lot of people, it’s more common now to see companies launch without the .com, and then get it once they’ve got a little bit of money going.

Drew: Because they’re all gone. [laughs]

Garrett: Yeah, but I think a lot of people, a lot of teams too, they don’t even worry about it at that point. They think you need a .com, and then you get going and you’re like, “Whatever, we don’t need it.” You keep shipping, and keep doing good work. It doesn’t matter.

It’s always interesting to hear the stories about how to get it, and also a lot of people are intimidated sometimes, like, “I’m afraid to even ask, because they’re going to ask for $200,000, or something absurd.” How did that go down for you?

Drew: In my case, it was more than just the .com. It was actually the whole brand. When I launched Quixly, I got the .com, because it was long-ago enough that you could find .coms. These days you can’t. I had Spacebox, and it was spacebox.io, and then I ended up getting spacebox.co from the guy who owned it by trading a domain to him.

He was another developer, so we traded domains, because he wasn’t using it. Then I was spacebox.co. and I couldn’t get .com. I was like, “I’m not going to have enough money for .com, they’re super expensive.” When I wanted to re-brand, I wanted to re-brand with a dictionary name. I came up with the idea of calling it Plastic.

I was like, “Sweet, I’m going to have a company called Plastic.” It looked just like that (pointing to the Plasso logo on the wall behind him), except it added an I-C. All I did was I tweeted about, “Hey, I’m super stoked. I just got the domain plastic.io,” or whatever I ended up getting. Yeah, it’s .io, coming soon or something like that.

From that tweet, a week later I got a little envelope in the mail, open it up, and it’s some other company saying, “Hey, cease and desist, give us all your property,” and all this other crap. I’m like, “Wait, what? How is this happening?” I had done trademark searches on Plastic, and there was nobody in the tech space using plastic, ending in a C or ending in a K.

I checked a couple other variations, but you can’t really do like searches with the patent search site. This company, they ended in a Q. I never thought to end plastic in a Q, so I ended up tweeting the CEO of the company. He’s like, “Hey, sorry. My lawyers are crazy. I always tell them not to do that, but they do. Don’t worry about it. Everything’s fine, just don’t use the name.” I’m like, “OK, fine. Prick.”

Garrett: Everything’s fine, just don’t use the name? [laughs]

Drew: Yeah, Just don’t use the name. They were saying they wanted the domain from me, and all this kind of stuff. I still have plastic.io, but I changed the name. I really liked what I did with the brand, especially the little A thing, and so I didn’t want to change that, because I had spent a bunch of time on it, and I already designed the site and everything.

I went looking for domains that were similar, and I was like, “What can I end this in that has everything available?” Plasso had .com, .org, .net, nothing was taken. Only the .com was taken, and it was past the expiration, it was past the renewal time. It was about to hit on the public market again that next month.

I was like, “Whoa, this is perfect timing.” I bought everything, and I didn’t tell anybody that I was going to, what the new name was going to be, because I didn’t want anything to happen. I ordered three different backordering services for plasso.com, and on the day that was supposed to drop, someone else somehow snagged it. I don’t know how that stuff worked.

Garrett: Oh, no.

Drew: I didn’t get .com, so I launched as .co. Then, when I saved up my pennies, I bought .com from the domain shark, just some random domain shark that had bought .com. I bought it from them, I think it was 4,600 bucks or something like that.

Garrett: That’s not too bad.

Drew: I bought it just over a year ago, I think. Maybe it was exactly a year ago from this month, or maybe it was last month a year ago, or something like that.

Garrett: Right on. That’s actually probably a pretty good deal for a nice short .com.

Drew: Totally. The reason I wanted to switch, because I’m totally fine with using other domains, is just because I want to take Plasso to the next, next, next level, and have it be the place where you go online to start a business. Why I do a .com is because I feel like the normal people more consider that.

Garrett: Absolutely. Would you say, now that you’ve raised money, you’re taking it to the next level, has it effected how you juggle work, and family, and all that? Is it pretty much the same, you’re still in control? Do you feel more pressure, less pressure, work more or less? How’s that changed or evolved?

Drew: Before, I was running multiple projects at the same time, and I would say most all of my career, I’ve always worked two shifts. I work in the day, and then I work in the night. That changed a lot after we had our second kid, and I stopped working the night shifts as much. I always still worked as much as I possibly could, trying to get something else to stick. What I found with Plasso, that did happen.

Last year was a little bit different to me, because last year I sold everything, we moved up to Washington state for six months because our families were up there, and then we decided we were just going to be there for a year, and come back down to Carlsbad. We decided we didn’t want to do that anymore, so after six months we bailed, and we got an RV, and we RVed the country for a year.

It was very different. I was only able to turn on my computer like 15 times the whole trip. Traveling, I thought I was going to have all this time, I’m going to get rid of all my stuff so I can just focus on Plasso. No, man, traveling is like a full-time job in itself. Then traveling with three little kids is super hard, as far as having time to do any kind of work.

Anyhow, last year was pretty different, but it reset me in the sense of, I had to go to bed early. When we came back to normal life, and we actually moved to Sausalito in San Francisco so I could raise money, it was impossible for me to stay up late and work. I was always, my body was just used to not doing that, so it was hard.

After raising money and moving back down here to Carlsbad, I got back into the swing of things. Now, I’ll often stay up and do my second shift, just because out of necessity, there’s so much stuff to do. Especially when you bring on a team of people.

Now that there’s seven other people besides me, it’s more than just me managing my own work. I have to always be thinking ahead about what each person can be doing, and then writing off different features and scoping them out, what I want people to work on, that kind of stuff.

There is a ton more to do, but what’s great about it is you write all these documents of what you want people to do, and all that stuff happens without you having to do it. [laughs] That’s pretty cool.

Garrett: Was that a pretty quick change for you, or did you slowly ramp up the hiring? Being somebody who is on your own, or not totally on your own, but more or less on your own working at your own pace, on your own things, versus now having to help keep everybody else busy. Did that change? Was that overwhelming at first, or was that an easy enough transition?

Drew: It wasn’t overwhelming at all. I had brought on three people before I even raised money. I was like, “Hey, I’m going to go raise money. I’ll give you equity for now, and I once we raise money, you’ll start getting paid.” All the people that I’ve hired, they all knew me, so they all believed that I could do it, that kind of thing.

After I raised money, then I brought on a couple more people. It all happened in 2016. Early 2016, I brought on three people, a few months later, I brought on a few more, and then a few months later, I brought on a few more. It all happened pretty quickly. By May, everybody who was on the team was already hired, or May to June. Yeah, June. The beginning of June. Within a few months, everyone was hired.

Garrett: Right on. Looking back at the last year, I guess this could even be the last couple years, before raising money. It may not even be for Plasso, but I’m guessing it probably would be. What’s been the toughest part, either the most stressful or most difficult, or just lowest point through this process of getting to where you are now? How did you bounce out of it, pull out of it?

Drew: Did you say not specific to Plasso, or specific to Plasso?

Garrett: It doesn’t have to be specific to Plasso. Just the whole bootstrapping a business, managing it. We’ve all hit those points, and then when you hit it, you don’t realize how normal it is to go through those ruts. It’s really, really difficult, but I think once you realize it’s normal, you just have to fight through it, that it really helps people say, “Wow, this is totally normal. It’s going to be a crummy week, but I’ll fight through it, and everything will be great on the other side” type of deal.

Drew: I’ve had lots of valleys, and I think every time, if you’re progressing, and if you’re doing better and better over time, I think your valleys get deeper and deeper every time, because you have more to lose every time. As you build up more, you’ve got more to lose every time you fall.

I get used to the fact that, “Yeah, I’m going to have burnouts.” I know when I experience a burnout, I know this is a burnout that’s only going to be temporary, but every time I have one, it’s worse than the time before. I recently went through that. Even after raising money with Plasso, I recently went through that.

It was more like, every time you put yourself out there, especially publicly, suddenly there’s a whole new weight on your shoulders to feel like you have to be successful. Like, “Oh my gosh, George raised money,” or something like that. “He’s blowing up, everything is going great for him.” [laughs]

Which it is, but at the same time it’s a lot of pressure, because most people who raise money just fall flat on their face. I’m no different. It’s personally a lot of pressure for me, because I’m putting myself up. I have a high expectation for myself, probably more than anybody else. For me to be successful, and figure out the best use of money, and all that kind of stuff, it’s a lot of pressure, and it can force you down into a valley, that kind of thing.

Thankfully, right now I’m not experiencing one, which is good, because that would suck, but yeah, it never stops. Probably the worst I had it was I spent two years in a code cave, working on my first piece of software that I was going to sell. You can go to firerift.com and check it out, the site’s still doing everything.

It was a client-side CMS, all in JavaScript. You could even access the database in CSS, yada, yada, but it was way too far in the future, no one had really got what it was. Which sucked, because I spent a lot of years, all my money. I was literally selling my furniture on Craigslist. I had a side business doing photography, I sold off all my camera gear.

We were expecting our first kid, and then we were going to have to foreclose on our house. We ended up short selling it. It was just the worst. As I was going through that, I launched Firerift, and it fell flat on its face. I was like, “This is terrible.” I remember, I was even expecting to be so successful that I went around looking at houses like, “Yeah, I can probably buy that thing, once this thing comes out.” [laughs]

I look back, and I was like an infant child, or something. Then this launch falls flat on its face, and I’ve got to launch something quick, something else. That’s where I came up with the idea of Quixly. I’ve been working icons on the side, and I’ll just sell these icons. I have no idea what to sell them for. There was only Glyphish, which was free icons, and there was Hlvticons, which was 249 bucks for 80 icons or something.

I didn’t know what to sell them at. I was lucky, because at that point I had no idea what I was getting into, but there was literally nobody else selling icons at that time. Nowadays, people sell them so much, it’s just a race to the bottom, and now you can get the best icons for free, but when I launched it, it was totally different. There was nobody else selling icons.

Overnight, I’m not even kidding, fall asleep, wake up to a bajillion tweets. All I did was say, “Yeah, I launched that thing.” At the time, I didn’t have a ton of followers. Everyone, I still have not experienced that to this day. Everyone is tweeting about it, and just overnight, my bank account filled up, and then it just kept that way.

I went from short selling my house to, I had a totally different lifestyle overnight, just because of that one thing. I got brought out of the valley. You never know when it’s going to come, or how it’s going to come, but obviously, you keep working hard. I was working hard. I told my son, who was six at the time, “You can’t just work hard, because people who work hard, they don’t always get what they want. You have to work smart.”

In that case, I was not working smart. I was just lucky. I feel like with Plasso, I was working smart because Plasso is not the result of luck. Plasso was the result of me trying this multiple times over, and trying to tweak things slightly. In that sense, I feel a little more proud about Plasso than I do about Pictos. The long-winded answer to your question.

Garrett: No, that’s good. In hindsight, I’m guessing looking back, you would probably say that you spent a little too much time heads-down coding, versus trying to put it out there, and see if anybody wanted it, or was ready for it, or whatever. Is it really just that simple? You would have said, “Hey, I’m going to time box myself to six months, and whatever I’ve got at six months, I’m going to find a way to launch it.”

Drew: That wouldn’t have worked for me back then, because what I did back then, I was like, “It’s going to do everything.” I would work on a little of this, a little of that, a little of this, a little of that, until it has everything. Years later, I came out with this book with my buddy Josh Long called “Execute,” talking about just getting it out there super quick.

In there, I talk about how you probably should do it, whereas you should give yourself a small goal. Not a big goal, but figure out what the core difference is, or the core marketing factor of your idea is. Just build something small around that, and then expand, expand, expand, after you’ve launched something small around that.

As long as you launch with a core idea intact, and people are like, “Oh, it’s this,” then you can always expand upon it, and people always remember, “Oh, it’s this.” Even though there’s much other stuff. More than just giving yourself a time limit, I think that would be setting yourself up for feeling like you’ve failed because you’ll still have all these grand ideas, and you wouldn’t be able to do them in six months.

Set yourself up with a super small feature set, and launch with that. That’s what I would have done…

Garrett: That’s how Plasso started, right?

Drew: …or at least I did since then. I’m sorry, what?

Garrett: Plasso was a lot more focused when it first launched, right? Or Spacebox, I suppose.

Drew: Yeah, Spacebox was super simple. It was just a one page deal. You sign up, and you connect a Stripe account, and there’s a page for someone to pay you. Right now, on Plasso, it’s our “Pay me” products. You go to plasso.com/youremailaddress, and someone will just go there and pay you money. That was what Spacebox was when it first launched, years and years ago.

Garrett: Indeed. I’m trying to decide which of these would be. For you, finding your first customers was a lot more, you’ve got somewhat of an audience and a following. For you, a lot of it is finding those first customers, spreading the word is coming from that audience, right?

Drew: Yes.

Garrett: Was that a conscious effort to develop an audience and reach people and create things that were of interest with certain audience or it just happen and then you said, “Hey, well, everything I’m building anyway is helping these people.” Was it a plan, or not necessarily a plan, but was it intentional or just a happy side effect?

Drew: A happy side effect. I just joined Twitter like everybody else and so just talking with people who are in the same industry as me that kind of thing. It turns out I like building things for myself, like things that I like using, so what I would build would be the same kind of things that other people likely would want, those who followed me so it just worked out that way.

Garrett: This may be a little too open ended. If you could go all the way back to when you first started launching businesses and you could do one thing differently whether that’s skipping a certain, “Well, no, we’re not going to let you cough up that easy.” [laughs] I would skip this business.

What would you do differently? What would you go back and tell yourself 10, 15 years ago to help avoid some pain, what’s the one thing?

Drew: I could go back in time and give myself a business idea but…

[laughter]

Garrett: Just changing how you handled things. We all could have gone back and bought the…

Drew: I think if I could it would be the same thing I just touched for real. It would just be to focus on a very small aspect and focus on the core of what my idea is and launch that, because what’s great about that other than you can launch soon you can also find out if it’s going to be successful soon or not without spending a bunch of money on it.

Then you could also market it much easier because you’re marketing one simple idea and you’re not marketing a whole slew of things, so it’s easier to find that.

It’s just all around easier, not if you launch with an MVP, Minimum Viable Product. It’s like broken into some spots or whatever or it tries to do everything, but just really in a slim way, not MVP at all.

If you launch with just a very small feature set built around that core idea that’s what I would go back and tell myself, because just from Firerift to Dialoggs each were two year-builds, before I launched it. I would have added four years of extra stuff like… [laughs]

Garrett: I wish I knew who I heard this from or where I heard it, but somewhere somebody replaced the viable in MVP with useful. What’s the minimum useful product? What can you create that’s going to give somebody value and help them and start there with that core?

The other side effect of what you’re talking about is as developers or product people, we don’t necessarily think about the marketing and the messaging and how do we explain this to somebody.

For every feature you add you’re adding support, your adding marketing effort, and overhead because you have to be able to explain it to people and make them understand what the value is, and a lot of features don’t have obvious immediate value so you’re complicating things by adding more burden for marketing as well.

That’s the quick version I’d like to keep them pretty dense. Is there any kind of parting words or advice, sentence of wisdom you want to share?

Drew: I’d guess I would say to everyone who’s doing bootstrapping, who’s kind of like purist mentality where like I bootstrap and therefore I deserve a cake or something, [laughs] business is a business.

Since Firerift I’ve consciously decided, “OK, I’m not going to treat my products like my babies,” because of the fact that my end goal for myself is not to have X company be the thing that I’m doing forever.

I have a lot of different things I want to do and there’s one thing missing in order to do all that stuff and it’s money, you need much money to do all these different things, I want to do, you want to do, whatever.

However I get there is however I get there, so I shouldn’t treat my products like my babies and I shouldn’t treat the path to success for this specific moment in time as like this purists kind of like my baby kind of thing.

Raising money is fantastic but you just have to go about it the right way. You have to make sure that it’s going to help you and if you’re irresponsible with money or you’ve never taken on risk yourself it’s probably not going to help you, but if you’ve been through the fire yourself don’t shy away from it.

In our industry it’s the most common thing in the world for someone to raise money, it’s so accessible that you should definitely consider doing it if you’re in that spot if you’re able to. If for nothing less than just personal experience and gain and insight and knowledge that you’ll get just from going through the process, I learned so much by going through that process that I’ve never even thought existed before.

I would just say don’t treat things like your babies at all because once you’ve, say, you’ve gotten supper successful with this company you’re working, what are you going to do next? Obviously it’s not your baby anymore if you move on, so yeah.

Garrett: I hadn’t written it yet, but there’s a new chapter in the book update that I tentatively literally have titled, It’s a Business Not a Baby.

I know from Sifter, I really just was so emotionally tied to it. If it wasn’t for going through my medical issues, I probably never would have let myself get detached from it because I was so focused on that stuff it enabled me to be like, all right, how does this fit into my life really at this point?

It’s hard to do in the moment. It’s easy to say but ultimately it’s a business, it’s an asset. You don’t want to treat it as just heartless asset, but at the same time you still have to have a bigger picture of you because it’s not going to be a sustainable business if you treat it like a baby and baby it.

Drew: Yup. If you go and raise money you’re going to be around people, hopefully you raised money from the right people who have been in your shoes multiple times over and not only that have actually helped other people in your shoes multiple times over, so you have people now on your team, your investors that are super smart and they’ll be able to help you through things that you wouldn’t be able to do on your own like running a big company.

There’s nothing wrong with going slow like bootstrapping, it’s totally fine. There’s also nothing wrong with exploding and running fast. Either way you have no idea what the outcome would be. [laughs]

Garrett: More often than not it’s not the raising money that was the downfall of a lot of these businesses, the businesses weren’t businesses to begin with, and somehow raised money because it was too easy to come by. But that’s a whole other story so we won’t go off on a tangent.

Drew: Yeah, I agree. I agree. People. [laughs]

Garrett: This has been great, especially adding the money-raising perspective to all of this, because I’ve obviously a bootstrap background here. I really appreciate it, and thanks so much.

Drew: Yeah, thanks for having me.

Garrett: Yeah, of course.


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