Omer (00:11.280)
Welcome to another episode of the SaaS Podcast.
I'm your host, Omer Khan, and this is the show where I interview proven founders and industry experts who share their stories, strategies and insights to help you build, launch and grow your SaaS business.
On this episode, I talk with Nathan Contney, the CEO of Highrise, the SaaS CRM app that was originally developed by the Basecamp team formerly known as 37signals.
Nathan is the co founder of two YC, Inkling and City Posh.
One of them is still in business, the other one failed and had to be shut down.
We talk about the lessons he learned from both those experiences and what he'd do differently now.
Nathan is also the creator of the online writing app Draft.
He built that product and business as a solo founder and he used blogging as a way to build an audience and get customers.
Now, that's a lot to do for any founder and we have a great discussion on how he managed to keep so many plates spinning and get things done without going crazy.
A few years ago, Nathan became the CEO of Highrise.
We talk about how he met Jason Fried, the co founder and CEO of Basecamp, and how that led to a job offer at Highrise.
And we discussed the big challenges that he's facing with Highrise and what he's doing about that.
Nathan is an experienced serial entrepreneur.
He's very transparent and shares a ton of valuable insights and advice with me and he's a great guy who I've really enjoyed getting to know better.
I think you'll enjoy this interview and also get a ton of value from it.
Nathan, welcome to the show.
Nathan Kontny (01:50.320)
Thanks a lot.
Omer (01:51.680)
Now, I already asked you this and whether you prefer Nathan or Nate, so you're good with both.
So I'm just going to call you Nate from now on.
Nathan Kontny (01:59.840)
Awesome.
Omer (02:01.600)
Cool.
I like to start by asking my guests if there's a favorite quote or a saying that drives or motivates them.
Is there something for you that's top of mind?
Nathan Kontny (02:11.680)
Yeah, I think there's just one thing that guides almost everything I do and there's all versions of this quote.
I think this is attributed to Sheryl Sandberg, who kind of said it in this succinct way, but it's just done is better than perfect.
Everything I do and probably everything.
A lot of the stuff we're going to talk about today is driven from this, that I just try to get stuff accomplished.
I don't want to labor over everything.
You can't predict the future and you just got to get it done and out there before you see the results of it.
So I don't let perfection stop me from trying to get the things I want done.
Omer (02:45.720)
Man, I wish I was like you.
I struggle with that a lot.
I'm kind of always, have always been like very much of a perfectionist.
And probably looking back, I probably waste a lot of time on little things that probably don't matter.
Or you could have just got, you know, get things out there, get feedback.
Someone once said to me, if you think about it in this way, in terms of, you know, the 80, 20 rule, apply that, get the 80% done, get something out there, get feedback.
And then the 20% you didn't do, try to do an 80% on that.
Just kind of like sort of iterate that way rather than trying to be sort of a perfectionist.
And when it comes to writing, that's something that I struggle with a lot because I'm terrible at just being able to get stuff out there quickly.
And we're going to talk about writing, but because you do a lot of it and draft is about helping people write better.
But yeah, it's just I'm gonna print out that quote and put it up somewhere.
I'm gonna start reading it every day.
There we go.
There we go.
Nathan Kontny (03:51.590)
Yeah.
No, and I've been there too.
I wasn't always this way either.
You know, the first, there was a thing I wanted to see in the world.
I thought my first startup was gonna be back in like 2003 or 2004.
I was working on this thing.
I was working on this like mobile version of a database administration software.
Like I saw mobile devices were becoming more popular then.
Not smartphones yet, but like PDAs.
You could run Java on them now.
So I started creating this like database tool on Java enabled Pocket devices.
And this is like way before its time.
The stuff is like prevalent today.
And I never released it, it never got done.
I mean it was this thing I just kept working on and working on and working on because it didn't have this feature.
Didn't have this feature.
That is one of those things I keep learning, looking at.
And it's just like, oh my gosh, I really wish I had launched that because if I had kind of turned that into a business, I think it would be a pretty successful business today given all the new infrastructure that's been provided that isn't just Java.
But I could have built it for Android phones, I could have just built it for iPhones, but I never released it.
So it's one of those nagging things in me that's just like, I can't let perfectionism because it's in me too.
I can't let it stop me from seeing a thing that I want out in the world.
So it forces me to find the balance.
Omer (05:10.310)
Yeah, I love that.
Love that attitude.
Okay, so in 2005, you co founded Inkling and got accepted into Y Combinator.
Tell us a little bit about that business.
Like, you know, what was it and where did the idea for it come from?
Nathan Kontny (05:25.430)
So we applied to Y Combinator.
I was kind of obsessed with this idea of crowd wisdom.
You know, I was working for at the time I had my first job out of college was at Accenture Anderson Consulting at the time, big, huge consulting company.
I went to go work for a much smaller software company after that for a couple of years.
But I was still very much kind of exhausted with, like, working at corporations.
And I always felt like corporations were making all these decisions, you know, based only on, like, the thoughts and opinions of just a few people.
I felt like a lot of us as employees had a lot of great ideas and input and insight and how things are going, but nobody's paying any attention.
None of this insight from us really trickles up very much.
I mean, sure, a manager might ask you something, but it's like, is this really getting to decision makers and how can we make that more democratic?
And I wanted to create tools that would maybe make working at a place like Accenture a better place.
So that's kind of what drove it.
And I also felt like I was also making all these decisions that I could have used help with, kind of drawing help from friends and just people out on the Internet, like, hey, do you think this is a good idea?
How can I gather that wisdom?
So Inkling was a form of a prediction market.
It was like this virtual stock exchange.
You could put out a.
Today, a lot of people kind of understand this concept, but back then, it was still very novel.
But it was like you could put out a stock not in a company anymore, but in a decision or a project.
You could say, is this project going to get done on time?
And then people could place virtual bets.
Even the employees could place virtual bets.
Like, yeah, I really think this project is going to get done by this date.
And if it does get done by this date, the people who bought into that stock can get rewarded.
Their virtual currency will increase, and the people who made bad bets, their virtual currency will decrease.
So it was just creating this virtual stock exchange that then we sold to small businesses, but mostly big businesses.
Companies like Procter and Gamble.
Anyone that had, like, a really huge crowd, they needed wisdom from.
Like, a really.
Some good customers of ours were governments, like the US Government, where they're trying to get, like, all this data from all these different, you know, government agencies and all these different employees of the government.
That's what Inkling did.
Omer (07:45.660)
So you were the CTO there for about six years, and the company is still around, but you decided to leave around 2011?
Nathan Kontny (07:57.360)
Yeah.
So now my partner, he took over.
He acquired the company and kind of roll it into another company where they're still kind of pursuing a lot of these projects to kind of corral the wisdom of the crowd.
But, yeah, at the time, we wanted.
You know, I. I've always really wanted to pursue tools in an industry that I knew very well, and it suited my own purposes so I could make much faster decisions.
Like, Inkling came from a place where, like, I thought I could use it myself.
But really the core user and the core beneficiary of gathering wisdom of a crowd is someone who has a really huge crowd.
So our best customers, like I mentioned, like, became huge.
Governments, banks, conglomerates.
And it's like, I love it.
I love that we were able to create that and put that out in the world.
But it didn't serve my needs at all.
It wasn't something I used anymore.
And so any time we needed to make a decision on how to make the product better, I couldn't use my instincts anymore.
It was always like, well, we better have a meeting with, you know, the folks at Procter and Gamble to see, like, what they need or if they like this.
And that's not where I want to be as someone who designs and builds products, like, I really want to be working much more for my gut and putting things out that I really believe in.
So.
So, yeah, I wanted to do something else and started taking some other shots.
Omer (09:14.370)
In 2011, is your kind of philosophy more about building the product that you want to see versus spending more time asking people what they want?
Nathan Kontny (09:26.530)
Absolutely.
I mean, it's not black and white.
I mean, I would never say, like, well, you can't do it the other way.
You'll never be successful.
But I do believe if you start with the stuff that's really.
That you know really well and suit your own needs, you know, that whole eat your own dog food kind of principle, I really think you improve your chances of success by a lot.
You know, no longer are you beholden to all this insight from people that's really hard to kind of gather sometimes.
Like, you know, we all know focus groups don't work often, and you can be led astray by a lot of people's opinions.
And even since then, I've looked for external validation from people and have been led astray over and over and over again.
And so, yeah, I mean, I really believe most people should start there.
You know, what problems do you face yourself?
And just start working on those before and run that well dry before you start trying to take on other people's problems.
Omer (10:19.990)
So you founded City Posh, which was your second YC startup, in around that time, 2011, 2012.
And this was kind of like a gaming platform, right?
Nathan Kontny (10:33.030)
Yeah.
So this kind of started from.
There's all sorts of little weird threads from this because it was like I was paying attention to the success of things like Zynga and Facebook gaming at the time.
You know, Zynga was taking off like crazy.
Everybody was playing Farmville and games like Bejeweled.
And I also saw, like, Groupon had been taking off and Groupon was doing well.
And, you know, we were kind of kicking around this idea of, like, well, what would be the next Groupon?
And everybody's complaining about Groupon being this.
Like, the only reason it works is because they're offering this huge discount.
But they were also kind of like an entertaining thing in people's lives.
Like, people were excited to get that email newsletter.
They were excited to buy a Groupon and go do something entertaining they've never done before, a restaurant they would have never tried before.
And so we were like, okay, well, that's interesting.
Can we do something for companies to help advertise?
Kind of like what Groupon is doing, but instead of the discount, we really focus on the entertainment thing.
So what if we built a bunch of games that people would play and we would borrow from all these popular game mechanics like Bejeweled and stuff, but these games were just advergaming.
Instead of Bejeweled, we would offer games like Bejeweled, but instead of Jewels, if we did business, say, with the Gap, you know, the Gap, instead of Jewels, could insert their own logos and images from their inventory.
You know, new sweaters they've got coming out for the winter.
And if we could provide a platform like that, people would be playing it and playing with all these brand images constantly.
Maybe then they would be, like, really attracted to, you know, next time they're shopping for a sweater, they would think Gap.
That was our pitch.
That was our reason for doing this City Posh gaming platform.
Omer (12:19.150)
So you weren't the solo founder for City Posh.
You had a founder, a co founder?
Nathan Kontny (12:24.590)
Yeah, yeah, he was actually my partner also at Inkling.
And so if you kind of listen really closely to like, and this might be the question you're about to ask, but it's like I just said I wanted to get out of Inkling because we were doing, you know, these projects for these big companies.
I basically screwed up again.
I mean, City Posh was a product for other companies and big brands.
You know, in the end, we didn't create something that was useful for us at all.
And I think that was in the end a huge reason for its implosion.
But yeah, we basically created something to help companies like, again like Procter and Gamble and people advertise on the Internet better.
Omer (13:03.060)
What do you think went wrong with City Posh?
Nathan Kontny (13:06.340)
So a variety of things.
One is we were doing this, like we were actually having some success with it.
Like people were playing our games.
Like on average we were getting about two hours a day per person, on average playing these games, which is when I was researching at the time was like Zynga level engagement in these games.
And so it was like, oh my gosh, we're doing great.
But then like, the problem was selling it to the brands.
It was like, you go to these brands, we would have meetings with important people.
Like we had meetings with Procter and Gamble, you know, we'd have a meeting with Microsoft and we'd be like, look like we've got this cool gaming platform.
People play it a lot.
And we think it could be the future or one avenue of advertising.
Like instead of just dumping your money on buying a banner ad, you could dump those same kind of assets and images and things into these suite of games that we've already built.
You don't even have to build your own game.
We've already got them built and have your fans and your social network play these things and just.
It's basically like they're playing a commercial for you all day long.
And it was interesting and we got meetings.
People definitely were interested.
But man, it was like a very hard sell.
It was like, well, what is the return on investment?
It's like, well, I don't know, because this is one of those brand building exercises.
Like people aren't going to just click on a sweater while playing the game and buy the sweater.
They're not going to buy diapers right away.
It's hard to quantify that this is working for one.
What I can quantify is that people are excited about it, but when you're talking to someone who wants an ROI on their ad spend, it's kind of difficult.
And then that was it.
We saw those difficult conversations happening and because again, this was another business for people that weren't like us, for startups, for solo founders, we were so uninterested in seeing this business through.
We had just spent six years building inkling with some of these same problems, and we were exhausted from these types of problems.
So it was like, I don't want to do this again.
I can't see a company.
I can't spend another six years working on other people's problems and seeing these tough sales conversations to completion.
So we kind of just gave up on it.
I really think there was something fruitful there, but it didn't have my heart.
I really didn't have the willpower to see it through because startups are hard.
All startups are hard.
But I couldn't complete this thing.
Omer (15:31.840)
So at some point, you sort of.
Well, it wasn't even a pivot, right, Because, I mean, you started focusing on draft, and it's still partly kind of operating under City Posh.
And I know I was kind of playing around with Draft and I got an email from idyposh.com domain back.
Nathan Kontny (15:49.290)
Yeah, my partner and I went our separate ways.
Like, my partner went back to the wisdom of crowd stuff, you know, running inkling and doing some, you know, fresh things there.
I decided, like, one, to take a break.
I needed to get my head a little bit.
I tried some things.
I was trying some other stuff, but I ended up taking a break.
I ended up working on the tech team for the Obama campaign for, like, six months.
That was hard.
And yet it was still more relaxing than running a startup, I think.
And it's crazy when people hear that because they know, like, whoa.
Working on a presidential campaign is really stressful.
It's like a lot of work, and it's like, it is, but it sure beats like, being up all night trying to figure out how to make money and find new customers.
It's definitely a different mindset.
And so I took a break.
I wasn't really in it for the politics.
I just really needed my brain in a separate place.
And I came out of that really fresh.
And I had been building an audience now for a while doing writing, and it was like, you know what?
If I'm going to really give this another go, I really need to focus.
I keep talking about it.
I got to focus on my own problems.
And I was like, I got to make writing software.
I've got a lot of pain points with writing, with collaborating with editors, and with version control of my writing.
I'm going to just start tackling these problems and see what happens.
So I had some money left over in the bank account from City Posh.
And so City Posh, the entity, is still around, but it helped fuel and invested in what became Draft, the writing software.
Omer (17:16.880)
So one thing I'm curious about is you guys went through Y Combinator with Inkling, and then some years, what, five years later or so, you went back again and said, okay, we have this new idea for City Posh, and you got into YC again with that?
Nathan Kontny (17:34.440)
Yep.
Omer (17:35.080)
Wasn't there a conversation about, like, why are you guys, like, trying to run two businesses?
Or why you're not doubling down on Inkling?
And did any of that sort of come up?
Nathan Kontny (17:43.600)
Yeah, not really.
I remember talking to Paul Graham about this, and it's like, they're always trying to take shots, you know, and they're doing this at such big scale right now.
So, like, if any investor is going to talk to you about something like this, it's definitely the folks at YC who are really interested in, like, taking new shots.
Taking new shots.
And, like, Inkling has been doing okay, but it's like, it's not one of these businesses that's exhibiting, like, really nice growth, you know, Like, I can't point to it and be like, well, that's really stupid because this thing is just, like, taking off like crazy.
Like, I wanted to take more shots.
Like, let's take on something that's, like, maybe gonna get more traction than even Inkling has right now.
So, no.
Paul's like, nah, of course, yeah, let's take another shot at doing something different.
I mean, there was like, a brief conversation, but it was like, oh, cool, you got another idea?
Yeah, let's take another shot at doing something fun.
You guys seem to know how to execute.
You guys still run a business, so it's like, you guys aren't going to, like, just throw away our money doing something really stupid so at least they could trust us.
So, you know, they buy into that and, like, they know people, like, take chance after chance after chance.
Like, some of the early founders, like, I love Justin Kahn.
He was a great example.
Justin was in the first batch of yc.
He created Kiko, was it an online calendar.
And then when, like, Google came out with their calendar, he was like, this is gonna be really tough to get much traction.
So like, he did another startup, you know, that became Justin TV and then that became Twitch.
And like, you know, they've got all of these examples of people who, like, Justin's smart.
You know, he obviously knows how to, like, get stuff executed on.
And it took him a little while here to finally land on the things, but they kept investing in him, giving him shots to.
To get another chance at doing something really remarkable.
Omer (19:32.710)
That's actually a really great example.
So it kind of totally makes sense that what do they say they kind of the saying goes, betting on the.
The jockey as opposed to the horse.
Nathan Kontny (19:42.150)
Right, right.
Omer (19:43.030)
Because there's plenty of the horses, there's plenty of ideas out there, but it's really about who are the people who can make those ideas, turn them into businesses.
Nathan Kontny (19:50.230)
Yeah, definitely.
Omer (19:51.430)
Okay, so Draft I can kind of understand.
Like, okay, so you found something that there's a problem that you can solve for yourself.
And I know that you had been spending a lot of time investing in blogging and sort of kind of refining that craft, but also, there's no shortage of writing apps out there.
I mean, maybe it was different back then.
So I was kind of wondering, like, what was the driver for you to say, I'm going to go and do this?
And this is why I believe I can do better.
Nathan Kontny (20:29.730)
You know, it came from a sense of, well, I know this space really well.
And so I was flush with different ideas.
And so, like, I could look at any writing program and be like, well, no one's doing any of this.
And I was very confident that no one was doing these things.
Like, you know, I could point to no one is doing version.
I mean, still to this day, I don't think anyone does version control as well as Draft does version control.
It's saving these major edits.
I can send a document and have the ability to accept changes, individual changes versus, like, you know, you look at, like, version control and software.
When you get a git pull request, it's all or nothing, you know, like.
Omer (21:11.890)
Right.
Nathan Kontny (21:12.210)
And that's kind of like what Google Docs is pretty much.
Although maybe they've introduced this.
I think they may have introduced this in the last couple years.
But, you know, Google Docs, by default, you send someone a doc and they're like, writing on top of you.
There is no, like, whoa, whoa, whoa.
I just want you to suggest a change.
Get out of my document and give me more control.
So, I mean, I could point to write, like, anything.
Like, Word was a good tool and there's good things, but it was like man, we're not going to be trading Word documents back and forth over email.
Like, everyone knows how that turns out.
And so I was just confident because it's like, I do this all day, I write all day.
I, I think I've got a pretty good.
Because this is like such a deep hobby career of mine, I can look at things pretty objectively and know that I've got some ideas I'm not seeing in all these other tools.
So it seemed like a good bet.
Let me start making some stuff to solve those problems.
And I'm not that naive about it.
Omer (22:11.200)
So it was just you working on draft and you were doing everything from building the product to thinking about marketing, writing, trying to get the word out there.
And quite often we hear that it's really difficult for a single founder to succeed and that you have to have a co founder if you're really going to have a shot at getting anywhere.
What do you think was different for you?
How were you able to make this work?
And particularly how are you kind of thinking about your time when you've got all of these things to do and it's just you.
It can really quickly get overwhelming.
Nathan Kontny (22:53.400)
No, I totally agreed.
And so there's probably a bunch of things.
So one, I forget who said it.
It's one of these popular VCs.
About the most difficult thing about a startup is just managing your own psychology.
I mean, and it's true.
I forgot who said it.
Maybe it's like Marc Andreessen or something.
But it's like you think it's like building a product, you think it's like doing marketing and you think it's like finding customers and it's none of that.
I think the biggest problem is just managing your psychology to, like, just keep going because, you know, running these startups and chasing ideas, there's bad odds stacked against you.
There's a lot of people that are going to say no.
There's a lot of problems you're going to face even if you have some success.
I mean, I look at even the people who've had a lot of success.
Like, you look at the group bonds and you look at Airbnb like these really fast growing companies historically, and they're full of problems that I know have driven the founders really batty.
You know, like, Andrew Mason's a friend of mine.
Like, you know, I know he went through a lot of stuff, Ed Groupon.
And, you know, just because Airbnb is part of yc, I know a lot of stuff early on caused so much Trouble for those guys, like, psychologically, I'm sure.
And so going through things like the startups already that I had been going through, I don't know, prepares me a little bit more to be a little like, mentally tough to take on a challenge, like being a solo founder.
Because one of the best things I think you get out of having another founder with you is simply just, it's the moral support, it's having someone there that you can complain to.
When you're feeling down, they can pick you up.
When they're down, you can pick them up.
And that's one of the big ones.
And so it's like, if you're really young and you are going to face starting a business as a solo founder, it's not impossible, but you got to be really aware of the toll it might take on you psychologically.
And if you don't have, obviously the co founder and you don't have maybe the mental toughness of doing it from startups for the past five, six, seven years with other people or whatever, you're going to have to find other ways.
I think kind of toughening yourself up.
Whether it's like, you know, you start taking on more physical challenges to really teach you how deep you can really go, maybe that's a version of it, or seeking professional help.
I think a lot more people should start seeing, like, therapists just to kind of make sure, you know, like, hey, are you doing okay?
Like, just psychologically, like, go get help.
That's okay.
It's okay to talk to people.
Or, you know, I luck out because I've got a wife.
She's always been like a really great silent partners.
So I can always go to her and talk through ideas or really lean on your friends and your network to be those, like, silent partners for you.
I think the whole psychological aspect of it is maybe the most important part.
And it's tough even for co founders, right?
Like, I'm running Highrise now.
We've got a lot of challenges and I've got like really smart people with me.
My, I consider my wife, she works at Highrise now as a co founder.
It's still really hard.
So, yeah, really focus on your psychology and keeping it right.
So, yeah, that was a big one.
That was kind of a challenge being a solo founder.
The other thing I also relied on too and still do is services that I can outsource.
There are so many great services today for doing everything.
Everything from like, I use Heroku because it's basically like having a DevOps team that I Don't have to have on staff.
They're making sure the health of everything is a.
Okay.
It's like a step up of just using raw Amazon web services.
Now I've got these people who are really focused on making sure I have all the tools at my disposal.
Everything is available, everything is going to be up and running and I can integrate with anything fast.
I also did things like accounting.
I outsourced really quick.
Indinero is a tool I've used really early on.
They're basically kind of an outsourced accounting and bookkeeping service.
There's a couple versions of this out these days, but that was another one where it was just like, I've got to get more help than just me managing my taxes and my bookkeeping and just hiring a cpa because I know how that goes.
You know, they're going to do the taxes, but they're going to still ask me to keep a lot of stuff in order.
So it was just like, I don't have that.
I'm going to outsource everything to the CPA service, bookkeeping service, even editing.
So like Draft has a professional editing mode inside.
And it was like, well, I don't, I can't do the edits myself.
I don't want to hire a bunch of employees myself because that's really tough to manage as a solo founder.
Starting to bring on employees and trying to manage them and get us do marketing and build a product.
So I hired my friend's company that had a bunch of basically outsource talent to do all sorts of different things.
The company's called Lead Genius.
Now they mostly focus on like outsourcing kind of, I think getting sales leads.
But back in the day you could kind of get them for a lot of generic tasks.
And so I hired them.
They were really smart.
A lot of college educated people were in their talent pool.
I could give them a document and be like, can you proofread this, make sure it sounds right?
So they were my editing site.
So I outsource everything I can outsource.
If there's a service for it, I will sign up for it so that I don't have to kind of run this in house.
That's a huge time saver and kind of like alleviates a lot of the mental overwhelming stuff that can happen as a solo founder.
Omer (28:22.640)
Yeah, that was a cool feature.
I noticed in Draft that you can just click this button and it'll take care of finding somebody who can edit your document for you.
Very cool.
Yeah, thanks.
Nathan Kontny (28:35.340)
Yeah, I mean that was another one that was just like.
That just came out of the fact that it was like, well, I'm constantly sending a document to an editor, like my wife or a friend, but when I don't have them around, I'm in kind of a pinch.
So it was like, well, how can I provide that for people with a click of a button?
Again, it was just one of those things that only happened because I knew the workflow so well of what I was trying to improve.
So, yeah, that was another one that was just like, it wouldn't have happened had I probably been asking people for what they wanted.
You know, no one's asking, like, oh, man, if you could just add this button to get a professional editor, that would be really great.
I've never had that feature request.
You know, like, it was only something that.
Because I knew it really well, it came to me.
Omer (29:19.200)
Right?
Yeah.
And talking about what you mentioned earlier about the psychology of being a founder and Airbnb in particular, it reminded me of that post I saw a while back from Brian Chesky, about when they were back in, whenever it was.
They were.
They were trying to raise, like, $150,000, and, you know, they reached out to, like, seven investors in the Valley, and five rejected them, and two didn't even reply back.
How many of us would have kind of, like, said, maybe given up at that point and said, well, if all of these investors think it's a sucky idea, then maybe we shouldn't spend a lot of time building this Airbnb business?
Nathan Kontny (30:04.300)
Right.
Omer (30:04.940)
It's crazy.
Nathan Kontny (30:06.060)
Yeah.
I mean, they've got so many versions of that story, too.
And I think, like, the reason they were able to kind of see that.
I only vaguely am familiar with this article because I think I've read it.
But, yeah, I don't have it.
And I'm gonna put words in Brian's mouth, but I feel like they've gone through so much stuff at that company that they have, like, super mental toughness.
Like, there was probably no problem seeing that through.
Cause, like, I know, like, even early on when they were starting Airbnb, like, Paul Graham thought it was a terrible idea.
You know, like, back in the day when they were actually thinking, like, people were gonna just have airbeds in random people's homes, because it wasn't so much like, renting a room or renting, like, a, you know, an apartment or house back then.
It was, like a legit.
They thought people were gonna, like, rent out airbeds.
And, you know, Paul Graham thought this was a silly idea.
But again, he, like, kind of believed in them, you know, like, well, they'll.
They'll figure this out.
And he saw how scrappy they were.
These were the guys, Airbnb were the folks who, when they were running out of money, they put out cereal.
Two cereal boxes.
This is during the first Obama election in which, you know, it was Obama and John McCain running for president.
And so they made two serials, Obama owes and like, I forgot John McCain cereal.
But they basically created the cereal and that's how they helped bootstrap themselves a little further, was selling the cereal because people were buying what is almost like collector edition cereals.
They've got tons of stories like that.
Omer (31:33.340)
I remember hearing that story that was like, crazy.
I was like, wait, how did you go from Airbnb to selling cereal?
Nathan Kontny (31:41.110)
Right, yeah, it was like a great example of like, they're scrappy.
They're going to do whatever it takes to keep things going.
And maybe those things are passed down for their parents or whatever they got through growing up.
But that's the kind of stuff, like, over and over again, I see some of the most successful people, like, being in the spot that I have been in now working, you know, doing two YC companies.
Like, I've got friends and colleagues that are like, it's pretty wild.
Like, I don't say this to brag.
Cause there's really nothing to brag about here.
But it's like, I know some, like, really crazy people.
Like, I remember, like when we started inkling having Steve Huffman and Alexis Ohanian, they needed a place to stay when they were still starting Reddit.
And so they slept on our couches in our living room.
Because, you know, Reddit wasn't yet, like the fourth largest site in the United States.
Wow.
In this circle of people, it's wild how many people, you just see them having to have gone through so many things to finally land on the really great idea or that marketing tactic that finally works.
You know, like, there's countless people whose stories I can't even tell because I think they.
They wouldn't let me.
But it's like they try thing after thing after thing after thing after thing, and then finally something works.
And so you can't give up the first time and the second, second time or the third time.
You got to play the law of large numbers or something and just keep doing it until something finally clicks.
Omer (33:06.550)
I think that's so important because it's so easy to paint a positive picture of building a business.
And you could say I'm kind of partly responsible for that with this show where there's, there's a lot of focus on, you know, how somebody built this business or how somebody built a multimillion dollar business or whatever.
And if you're an entrepreneur who is still trying to get traction or trying to figure out the right business idea, it can be pretty frustrating just to hear all of these stories where it sounds so easy for people to have built those businesses.
And like you're saying, often the reality is that it wasn't.
And maybe I need to spend more time digging into all the things that went wrong with people without depressing everybody who's listening.
Nathan Kontny (34:01.730)
Yeah, right, right.
It's tough because it's like people don't want to be depressed constantly.
You don't want people just complaining about how everything is terrible.
But the reality, I think, is always much crazier than people realize for most, most of these people's stories.
And a lot of people, I think, are embarrassed by some of the things that they failed at, that they don't bother sharing them.
They don't think people would be interested in hearing these things.
But it's like, I don't know, you know, like, I've made so many mistakes.
And even in High Rise, I mean, we still make a bunch of mistakes and we still get frustrated and we still want certain things to be working out better and we just keep taking shot after shot after shot.
But from all of this experience of my past, that's how it works for everybody.
Omer (34:46.920)
So I want to talk about Highrise, but before we do that, I just want to kind of close off on draft.
So we kind of talked about you having to be the solo founder, having to do everything, so you're having to think about improving the product.
And I know from the research I did, you were releasing new features at a pretty steady rate.
Then you're doing a lot of writing, then you're having to think about customers, you're having to think about, you know, the DevOps stuff, all of that.
How did you prioritize your time?
How did you decide what you were going to work on?
Nathan Kontny (35:22.310)
Well, this is something that I really.
I started with Draft.
We do it today at Highrise.
But it's like I really got obsessed with cycles.
And this goes back to the quote that we talked about in the beginning that done is better than perfect and you don't want perfectionism to kind of creep in.
But it does and it does for me.
You know, like, there's a feature I'm working on right now that it's just like, I kept asking for, like, can the font size be bigger?
Can we change the font color here?
Can we move it over to the right?
Like, does any of this matter?
Maybe not.
But I'm also a very stickler for like, you know, really perfect design details.
So how do I not get haunted by that and cursed by all of that?
Well, so at Draft, what I did was I implemented to myself.
Every three weeks, I'm going to send out an email newsletter to every single person using Draft and it's going to tell them something new about the product, hopefully three features.
I better not send out a newsletter that has nothing on it.
So that cycle became this like, forcing function for me that like, I knew in three weeks I'm going to have to send out a newsletter, there better be three things on it.
And so that was the, a huge force, you know, because at the beginning of the month it's like, well, there's a lot of cool stuff I could work on.
You know, there's feature requests, there's, there's stuff I'd like to see, there's improvements.
And so you start tackling some of the stuff and, you know, the big stuff seems doable and you start working on a two week project and then you get real close to that three week window and you're like, oh my God, this isn't going to be done in time.
I need to find three fast things to work on right now so I can still send this newsletter out.
That forced me into a way to prioritize things like, yeah, I sure would like this new way.
There's a way of, there's a button you can hit to get your document kind of improved.
There's like a bot that will suggest improvements in your document.
And the version that that's there now is like pales in the comparison to this version that I really was cooking up.
This version I was cooking up was going to like auto trim your sentences and make your whole thing more concise.
Based on this, like, academic research, I found of someone who was able to pull this off.
And it took me months of work, but every time I got to that three week window, it's like, well, I'm not there.
I'm not done with it.
So let me find three things that I can get out this month.
That was the driver.
That's what helps me kind of eliminate the perfectionism thing.
It's like, I don't really care what I get done as long as the momentum is there.
And so that was a Big part of draft.
It's like, yeah, I got a lot done.
Sometimes they were big, sometimes they were small, but I always got a bunch done.
As long as I was able to announce something and show people the momentum I have in the product, that was it.
That was like, the biggest priority is show momentum.
Things like support.
At Highrise, we love doing this.
Really great support.
We can.
We've got a really great support team, but like a solo founder, like, if you're trying to make a product and there's a lot of stuff to do, you might not be able to do the greatest support.
Like, own it, don't fake it.
You know, like, you'd send support and it would just go to my, like, email, you know, and sometimes I wouldn't get back to people.
It wasn't the greatest experience, probably, but that wasn't what I was optimizing for.
If you want to optimize for it, go for it.
But it couldn't have been my top priority because you can only have one priority and my priority was product momentum.
So support requests, if they weren't urgent, I'd get back to it in days or weeks.
Sometimes feature requests, I'd say thank you, but not terse answers.
That's it.
That was a big one.
Really figure out what your 1 priority is and optimize for that.
My mine was momentum.
And everything else really kind of got taken care of on its own.
Even writing that was based on a cycle basis, too.
Since when I started Ninjas and Robots, a blog that I had created, I think it was in between City Posh and Draft, or while I was doing City Posh, I committed to just getting one article done a week.
I promised Dustin Curtis, who invited me to his blog network.
Subtle at the time.
He said, in order for you to be on this thing, you got to do one article a week and that's it.
And I've kept that habit of just getting myself into a habit of just publishing something once a week.
Again, I don't even care what it is.
I try my best.
If I've got a lot of time in front of me, I try to get an article done that's got a lot of research and a lot of cool storytelling.
But even this week, I've gotten a lot of stuff on my plate.
I published an article a week ago that was basically just a transcript of a vlog I did.
Like, I just quickly went through the transcript, kind of cleaned it up, and it's like, it was good.
I was fine.
It might not have been the Thing I would have written had I had a lot of time on my hands.
But I'm on a cycle, so I've got to get it out the door.
So I do a lot of things in these cycles.
They force me to get stuff done.
Omer (40:19.550)
So you mentioned Heroku and Indinero.
I was just curious in terms of were there any other services that you would recommend to people maybe listening that they may not have maybe thought about beyond the obvious things like, yeah, I'll use GitHub or whatever.
Nathan Kontny (40:36.890)
So I use Engineer for draft.
I use a combination of things though these days for.
There's a lot of startups now doing all the same stuff kind of in the space, but things like Zenefits is out there.
We use Gusto for payroll.
Bench is another good one for bookkeeping.
So these are some good services that we use for doing any of these administrative functions.
Lead Genius now doesn't really do the thing that they did anymore, but there's versions of that that I think people don't tap into quite enough.
Is TaskRabbit still around?
Maybe there's versions of TaskRabbit that are out there that I think are ripe for still kind of including in your life to take on a task, maybe if it's even a marketing task.
There's someone that I. I've tried a little bit.
They weren't right for me at High Rise, but maybe they would have been right for me in a different function that I'm kind of excited about.
But it's like they do like On Demand.
I'm gonna screw this up because, like, I don't have a name at the top of my head.
They like do On Demand design.
Maybe we can look this up in post.
But it's like they do on demand design work.
It's again, it's like you can outsource this design work.
You don't have to have maybe a designer on hand.
Maybe you need a quick email design or you need a postcard or you need a PowerPoint deck.
So these guys are on staff and they could quickly spin up some of this stuff.
But yeah, I would just keep your eyes open for more of these services that just keep outsourcing away from your core function.
If your core function is to building really cool stuff, how many services can you hire just to do all those extra things?
There's a lot of them.
Omer (42:12.380)
So you moved over to.
You joined Highrise.
What's the current state of draft like?
Do you still have people working on that?
Is it still in active development?
Nathan Kontny (42:21.740)
I keep it up to date.
You know, I keep it patched.
I keep answering support emails, and so I keep it running.
I do that, obviously, because I want to keep customers happy because they keep paying for it.
I mean, Draft keeps making money every month, but I also use it still constantly.
Like right now, as I'm talking to you, I have Draft open with answers to possible questions and things that we could talk about in this interview.
So I use it every day.
It's like, open all day long.
So I have to keep it running or I'd be at a loss.
I still don't think there's a tool that quite matches what I wanted it to accomplish.
Omer (42:55.850)
How do you make money from Draft?
That's one thing I couldn't figure.
I couldn't find a way to pay
Nathan Kontny (42:59.970)
you for anything if you haven't made enough documents.
If you've made enough documents, there will be a button that says unregistered at the bottom left that'll pop up eventually.
And so it's this thing that I let you use for free, but then I start nagging you a little bit to try to pay me.
And so there'll be a button that shows up as unregistered, and you click it and you can pay me.
That's it.
You click it and you can pay me four bucks a month.
Or you could pay for edits.
I make some money from the edits, but the edits that.
It isn't a very profitable exercise because I obviously have to pay someone to then do those edits.
I basically just try to encourage you to pay me.
Use this product for free.
You don't really get much else.
If you do pay me, you get the satisfaction of not having this thing, say unregistered in big letters on the thing.
There's things like a little community that's not very active anymore who talk about writing.
You get a discount in the pro editing.
It's one of those things.
It was an experiment.
It worked out okay.
I kind of liked it.
I feel like if I were to take another crack at it, I might take a crack at doing more freemium stuff, like offering the product still for free, but maybe holding back some of the features unless you upgrade.
But at the moment, I don't have time to fool with it.
But I think that's where I would start experimenting if I did.
Omer (44:17.650)
So I know you don't talk about specific revenue numbers, but can you kind of give us a sense of, like, how big the business is or maybe how many users you have or, you
Nathan Kontny (44:27.610)
know, oh, man, I've like lost track.
A number of users a lot like it because it's free.
A lot of people have picked this up.
So it pays these days.
I mean, it was growing there for a while and then I may have like ticked down now in the high rise days.
But it makes enough to pay someone to work on it.
Probably.
Like, I probably should hire somebody to do things, but that's about it.
It pays enough about a salary to.
To hire someone who could maybe work on it full time or part time.
It's still relatively small, but it's only now because I think it would be much bigger if I were spending time on it.
I really haven't been able to spend any time on it since taking over Highrise.
Omer (45:07.300)
I just love the.
How well designed it is, the simplicity and the fact that you don't realize it can do all this stuff because it looks so simple, but once you start kind of peeling away the layers.
Oh, wow, that's pretty cool.
I didn't know you could do that.
You know, like the kind of the feature we talked about earlier.
I think that's what is a big part of the appeal, certainly when I.
When I look at it.
Nathan Kontny (45:31.530)
Thank you.
Yeah.
And I mean, I think that also goes into the.
You know, I made design decisions here that I think were also to remove one.
It was an esthetic that I enjoy, but it was also from necessity.
Like, as a solo founder, I don't have time to spend on making all these bells and whistles and frills, like, more well designed.
So I really try to strip it down to just the basics that won't be hard for me to design quickly.
You know, I think a lot of people, they bite off these projects and they're like, well, I need a designer because it's got to do all this stuff.
And it's like, well, does it really.
I mean, if you really strip it down, like, it could just be a white page and some text and you could read a book to get a little bit better about how to get better about managing white space and learn a little bit about fonts and there you go.
You don't really need any design.
There's a lot more to that, I think, in people's businesses.
When I talk to them about what they've got dreamt up, it's like, well, that's really great.
It'd be great if you could have all of that stuff, but it's probably going to require hiring people.
People.
Can you strip it down just to some real basic stuff?
That I don't get it out the door with just the basics and then you can see where it goes.
And a lot of people, I don't think do this enough.
They don't go through that exercise of like, okay, what is really drop dead critical?
Can I just throw this away?
Can I get rid of this?
Does it really have to even have this fanciness to it?
Just ditch it.
And what you're left with is often, I think, pretty manageable by just one person.
Omer (47:09.390)
Did you use any libraries like Bootstrap or something for the front end or did you just build that yourself?
Nathan Kontny (47:14.830)
No, I did use Bootstrap, which is interesting.
That was one of the design decisions.
I did use Bootstrap, but I refused to make it look like normal bootstrap.
That's one thing that I think a lot of people get a little lazy about.
They take these things that obviously Bootstrap is a really nice framework to give developers a nice leg up in terms of design.
It gives them a design framework that they're maybe not used to dreaming up all on their own from things like responsive grid frameworks and CSS classes, but then they just go ahead and use the default bootstrap theme.
Yeah, everybody has seen these sites over and over again.
If I was going to use Bootstrap, it was like, I'm going to just completely obliterate the old design and change everything.
But yes, it just uses Bootstrap.
But, but I made a big effort to like, well, this isn't going to look like another Bootstrap site.
Omer (48:09.570)
Yeah, well, it's very well done.
Is Hirise still part of.
I mean, I know it's a spun off as a separate company, but people like Jason Fried still kind of actively involved in the business.
Nathan Kontny (48:21.810)
Definitely.
So they're the parent company, we're a subsidiary.
I mean, it gave us spinning off as a separate business, gave us the enough room to kind of do our own thing, hire our own people, you know, really do our own thing.
But yeah, Jason and David still sit on the board of directors and we're still, you know, a wholly owned subsidiary of Basecamp.
Omer (48:41.000)
So how did you end up getting that job?
Nathan Kontny (48:43.560)
Just loose connections, you know, like, I've been good about.
I've been good.
I wouldn't say I'm the best at this.
And I really also recommend people get better at this.
I have a friend, Harper Reid, who was the CTO at the Obama campaign.
He did Modest that was bought by PayPal.
The guy is the king of keeping loose connections around.
He reminds me There's a story about Bill Clinton using these notebooks ever since he was a kid.
He'd write down every single person he met in these notebooks.
And so that when one day he was gonna become president, he had this huge network of people to call on for things like donations and help.
Harper's the same way.
I think even he had a notebook just like Bill Clinton.
I don't even know if he realizes Bill Clinton used to do this, but, like, Harper did the same thing.
And the guy is just flush with so many network connections just because he likes to say hello and make sure he remembers who you are and will say hi to you again in the future.
That's how it worked out with Jason.
Like, Jason Freed.
I met him at some sort of tech event back in Chicago in, like, 2006 or something, and I said, hi, hey, I read your blog and dig what you're working on.
And ever since then, I've just gradually kept that loose connection alive.
An email here, an email there.
I'd email someone on their team about some security problem I found or something like that back in the day, and just kept that relationship alive.
And then when I started Draft, because this connection is alive, I sent him an email that was just like, hey, would you be interested in ch.
Chatting about product design?
I'm working on some writing software.
I know you like writing.
I know you like simple tools.
You want to just get together every now and then in chat so that we started meeting up and just talking about Draft every now and then.
And he'd show me designs for Basecamp and stuff like that.
And then.
So, yeah, when they announced this whole hire that they wanted to spin Highrise off, I was this obvious candidate because I've got this connection with him.
And so really, I think it's just a lesson in just keeping a lot of loose connections alive.
It's okay not to make everybody your best friend, but put some effort to keeping a CRM or just even a notebook around, meeting new people.
Omer (50:52.920)
What's your focus at Highrise?
What's the most important thing for you there?
Nathan Kontny (50:59.000)
When we started, it was a lot about product momentum.
A lot of people, unfortunately, thought Hirise was shutting down.
The news wasn't delivered the best that Highrise was looking to spin off because there was some language that, like, well, Highrise is we're looking for someone to buy it.
And people got worried that Highrise was shutting down.
And we had a lot of competitors that, like, fueled that fire, unfortunately.
And so we really needed to breathe some new life.
Into the product.
So the first half of what we did was just really, like, focus on cycles of getting features out, you know, convincing people that we're still around and.
Or this product is important to us.
Right now, it's all marketing.
We still need a bigger flywheel for marketing.
One of the benefits of kind of spinning away from Basecamp and 37signals is, like, now we get our own resources and our own room to do stuff.
But one of the curses of that is we don't really have that same halo that, like, we get it a little bit, but it's not very strong anymore that, like, Highrise is a Basecamp brand or a 37signals brand.
Jason and David and Basecamp, they do really well spreading the word out about themselves.
They're very influential figures.
But that halo kind of decreases now, so we really need to kind of figure this out ourselves.
So, yeah, I mean, our core responsibility, our core focus today is getting much better about getting the word out about High Rise.
Omer (52:26.800)
It feels like a product that's just right up your street, right.
In terms of a simple CRM, a big focus on great user experience, taking a lot of the sort of the complex functionality that maybe you'd expect to have behind a CRM and finding ways to either simplify those features or present them to users in a simpler way.
Kind of taking a lot of the sort of the same philosophy that maybe you've applied with Draft into High Rise.
I don't know.
Maybe that's what Jason was thinking.
Nathan Kontny (52:57.740)
Yeah, no, and I agree.
I thought it was the perfect.
And that was the reason I took this jump.
I mean, I thought it was a little bit of a risk because I was like, Draft was really doing pretty well, getting the word out and seeing growth.
And it was like, I want to jump into High Rise and do this crazy project that's kind of like a very unknown thing.
And it kind of turned this company around because it hadn't been given much attention for a long time.
And it was like, yeah, I do.
Because it's one.
Highrise has been a tool since.
I've used since all my startups, you know, and we needed a sales tool to talk to customers.
At Inkling and at City Posh, we used Highrise.
And so I was very comfortable with the domain.
I was very comfortable already with the tool.
I knew things that I wanted it to do.
You know, I wanted to get emails inside quicker.
I wanted it to do both bulk email and there's that.
Then the philosophy of, like, definitely keeping something simple, realizing people are probably most of us are coming from, like, Excel and, you know, a group inbox or something that we don't need all the bells and whistles.
We just need our first kind of step into sharing, you know, a group address book, notes and emails with a team.
It was totally right up my alley.
So, yeah, I thought it made a lot of sense.
Omer (54:14.590)
One thing I want to make sure we also talk about is your YouTube channel.
So that was something that I guess you started about a year ago.
Nathan Kontny (54:24.190)
Yeah, like, I started dipping my toes in the water maybe like a year and a half ago, but I got serious about it a year ago and then.
Omer (54:31.230)
So have you basically been, like, vlogging like, every day since then?
Nathan Kontny (54:35.550)
Yeah.
So, yeah, on January 1st of 2017, I told everybody, I'm going to film a video every single day.
And I was pretty good about it at the start.
And then it started fading.
There was a number of reasons.
Like, I don't know, I started getting, like, pretty obsessed with the numbers.
And I thought maybe when I wasn't doing a video every day, I was seeing better subscriber growth and I was just.
I was trying to game things too much.
Then I kind of lost motivation, and so then I was just like, you know what?
Screw it.
Like, I'm going to stop paying so much attention to the numbers and gaming this thing and just keep committing to it and trying to get better than the day I was before.
And so then I forgot when it was.
Maybe forgot when I did that.
Maybe back in, like, July or June.
I, like, recommitted myself.
And since then I've been pretty steady.
I think I got sick one week and missed a few days.
But almost every day since then, it's been about a video.
Every single day.
Omer (55:28.390)
I subscribe to the channel and I'll include a link in the show notes for people who want to check that out.
But yeah, I mean, certainly it helped me to feel like I knew you better before we.
We had this conversation, which was.
Which was awesome.
It reminded me of what you said earlier about, like, the forcing function and.
And I think I might have heard you say this in one of your videos, where probably it kind of almost put you in a place where you were kind of from the time you woke up, you were thinking about, okay, what's the.
The story or the lesson or the point that I want to make to kind of deliver some value with my YouTube video for today.
Nathan Kontny (56:06.520)
There's so many cool benefits.
Like that one, like you mentioned, it felt like you got to know me on this YouTube channel.
And that was a huge thing I wanted to kind of produce, which is like, I don't think we get to know enough of our.
The people we do business with.
You know, like, you spend money at so many companies and you're just another dollar to most people, and you don't know them and they don't know you, and.
And it's like, it sucks, you know, like, I enjoy doing business with the companies that are a little bit more open about themselves when they tell me about, like, you know, the challenges and things that went into making their products.
And they get more loyalty from me.
And so that was a big part of it, just opening up and showing all the stuff that I go through, even if it's like showing the challenges of raising a kid.
You know, some of these vlogs are not even about business.
They're about, like, my kid's sick.
How the heck are we going to get through Christmas like this and then two.
Yeah, I mean, it is.
It's this forcing function to find something creative about the day.
Some lesson from the day.
You know, it helps me appreciate the day.
You know, like, so many days run in together.
I think for a lot of us.
Right.
You're constantly doing the same thing.
You got another interview, you got to send another email out, and before you know it, you look back and just like, I did the same thing every single day.
Well, this at least helps me find, like, one little nugget that, you know, sometimes there's something huge that happened in the day, but often it's just like, well, I'm going to really have to force myself to look really hard to find that one cool thing that I could teach someone or appreciate.
So I like that aspect of what it does for me internally as well as kind of what it does for the business and how it offers, like, another way of communicating with customers and fans and stuff like that.
Omer (57:49.860)
Yeah, I mean, it's certainly, you know, when you think of the Sea of Highrise, you don't think of a YouTube channel, and a lot of people don't do that.
I mean, I'd thought about doing a YouTube channel at one point and it was like, I don't know.
I think it'd be pretty boring.
I don't know what I would kind of put on there, and I'm not really sure if I'm that comfortable, like, you know, putting it all out there.
Nathan Kontny (58:12.300)
Right, sure.
Yeah.
Omer (58:14.280)
And so was that something that you had sort of done before, like, even little things, like, you know, what wasn't a Little thing, but, you know, with your.
With your daughter being sick.
And I remember it was like, hey, you know, we're supposed to go around to some.
We got some event going on tonight and stuff like that.
And were you comfortable, like, sharing that kind of information?
Nathan Kontny (58:35.880)
Yes and no.
The answer is it's complicated.
I mean, like, I have had some experience.
I of.
You know, I've done acting classes, like, for years.
Like, I love acting.
You know, I've been in some little things.
A film here and there, student films.
I've been in a play, et cetera.
I'd like to do more of it, and I don't get to.
So I've had a little experience with this.
But the flip side of this is, like, I'm a huge introvert.
Like, I don't spend a lot of time with people outside.
I mean, I really like meeting new people and I like making friends and, you know, like, these loose connections I was just talking about.
But, man, I don't like going to parties.
I don't like being in crowds.
I don't really love drawing attention to myself.
And so when you've got that camera and you're talking to it outside in a public place, doing a vlog like I do, it draws attention.
And it's really not.
I don't like it.
And yet what I've recognized in my life is that so many of these pivotal moments for us happen when we put ourselves in a moment where we are probably going to be embarrassed or we're not going to feel good about it.
And I see that in my life so often.
There were these moments where, you know, great things happened because I put myself out there and I thought.
I thought, like, I was going to be embarrassed.
I was going to look like an idiot, but I didn't.
Not all of them worked out, but I didn't die or I didn't get embarrassed.
You know, like, yeah, I emailed that guy and wanted him to invest in me.
It didn't work out, but who cares?
Like, I've moved on and doing enough of that.
It's like, well, you know what?
I'm gonna do this.
Like, I'm gonna put that, you know, walk around talking to a camera.
Who cares if people are looking at me and just do it?
And it took practice, and it still takes practice.
I mean, now I can do it a little bit more freely without really cringing on the inside, but I'm still not super comfortable with it.
So it's just one of those things that I think you kind of have to recognize about yourself and tough through it and just recognize that if you can kind of get through an embarrassing moment like this, there might be some really cool thing that happens as the result of it.
Omer (1:00:42.080)
All right, well, I'm gonna include a link to the YouTube channel and go and check it out.
You can learn more about Nate and you'll learn a thing or two.
I certainly already have.
Nathan Kontny (1:00:54.580)
Awesome.
Thank you very much.
Omer (1:00:55.740)
Yeah.
Let's get on with the lightning round then.
So I'm going to ask you seven questions.
Just try to answer them as quickly as you can.
Are you ready?
Nathan Kontny (1:01:03.700)
Sure.
Omer (1:01:04.740)
Okay.
What's the best piece of business advice that you've ever received?
Nathan Kontny (1:01:10.100)
Why haven't you launched already?
Paul Graham asked this, I think, to everybody, like, get your product out.
Why isn't it launched already?
Stop delaying.
Omer (1:01:18.020)
What book would you recommend to our audience?
And why?
Nathan Kontny (1:01:21.870)
Something really new.
It's one of these business books that no one seems to have read.
It all is about kind of like innovative things are all about simplifying people's lives.
That's it.
It's really simple.
Read the book.
It's something really new.
Omer (1:01:36.270)
What's one attribute or characteristic in your mind of a successful entrepreneur?
Nathan Kontny (1:01:42.510)
Someone who just gets stuff done.
It doesn't matter what tools that they have.
They're going to use anything at their disposal to get it done.
They can build it with duct tape and glue if they have to.
Omer (1:01:54.650)
What's your favorite personal productivity tool or habit?
Nathan Kontny (1:01:58.650)
These cycles that we've talked about?
Publishing two articles a week, publishing a new video every day.
Get yourself on some kind of cycle in your business and personal life.
Omer (1:02:08.330)
What's a new or crazy business idea you'd love to pursue if you had the extra time?
Nathan Kontny (1:02:12.730)
I don't know.
Building the next YouTube, maybe?
I love doing this YouTube vlog, but there's a lot of cracks over there.
And if I really had all the time in the world and all the money to spend on it, I would maybe take some shots at doing a video startup.
Omer (1:02:26.690)
What's an interesting or fun fact about you that most people don't know?
Nathan Kontny (1:02:31.010)
I used to be a figure skater.
Omer (1:02:33.490)
Really?
We could have a conversation about that, too, definitely.
And finally, what is one of your most important passions outside of your work, I mean.
Nathan Kontny (1:02:46.550)
Outside of work, it's my kid.
I mean, that's it.
It's being a parent raising my kid.
That's the most important thing.
I mean, that seems obvious.
If it's not that, it's the vlog.
I'm really obsessed with improving this vlog and video.
I'm really kind of excited about the future.
Video has awesome.
Omer (1:03:03.710)
Nate, it's been a pleasure.
It feels like we could talk for hours, but I've got to be respectful of your time.
Nathan Kontny (1:03:11.630)
No, no.
Yeah.
And if you want me back on anytime, seriously, I'd love to chat more.
Omer (1:03:15.630)
I would love to, and I will definitely take you up on that offer.
It's.
It's public now.
Yeah, yeah.
Nathan Kontny (1:03:21.310)
Don't hesitate.
Seriously, email me anytime.
Omer (1:03:23.390)
So if people want to check out Draft, they can go to draft in dot com.
And if they want to check out highrise, it's highrisehq.com right?
Nathan Kontny (1:03:37.600)
Yes.
Omer (1:03:38.480)
And if people want to get in touch with you, what's the best way for them to do that?
Nathan Kontny (1:03:42.000)
I'm really active on Twitter.
Twitter is a good one for me.
Just my Nate Cotney.
N a T K O, n T N Y.
But also email me if anybody's got any questions or you need help.
No one should hesitate to reach out to me.
Sometimes I'm not the best at getting back, but I will try.
Just.
It's Nate n a t cotneymail.com awesome.
Omer (1:04:03.180)
Appreciate that.
Okay, cool.
Well, I wish you all the best at Highrise.
Sounds like a fun and challenging gig over there.
Nathan Kontny (1:04:13.900)
Yes.
Omer (1:04:14.860)
And, yeah, I would love to get you back, and maybe we can talk more about what you're kind of learning with being the CEO over there and the life of a vlogger.
Nathan Kontny (1:04:24.380)
Cool.
Yeah.
Omer (1:04:25.900)
Awesome.
Thanks, Nate.
It's been a pleasure.
Nathan Kontny (1:04:27.780)
Yeah, no problem.
Thank you.
Cheers.
