Brian Donohue on Operating Instapaper Through an Acquisition

by Y Combinator11/14/2018

Brian Donohue is President of Instapaper and a Product Engineering Manager at Pinterest.

You can find him on Twitter @bthdonohue.


00:00 – The history of Instapaper

8:00 – Free competitors enter the market

10:00 – How Brian joined Instapaper

14:15 – Transitioning from paid to freemium

19:00 – Pinterest’s acquisition of Instapaper

26:15 – Moving to California

28:45 – Working on Instapaper within Pinterest

32:00 – Spinning Instapaper out of Pinterest

42:15 – Jareau Wadé asks – What types of product integrations could Pinterest have done with Instapaper?

49:45 – Ryan Hoover asks – I’m curious how he and the team balance simplicity with new feature development/product expansion.

54:00 – Raymond Durk asks – I love the rapid reading mode but would also love a voice enabled mode where the Google Assistant or Siri reads it. Speaking of I’d use it on my Google Home to listen to news if that was a skill.

57:20 – Brian Kim asks – Any growth hacks that worked well?

59:45 – Gustaf Alströmer asks – How does it make time for focused time to catch up on everything he saves? What are his best productivity hacks related to this?

1:03:25 – Backpacking


Google Play


Craig Cannon [00:00:00] – Hey, how’s it going? This is Craig Cannon and you’re listening to Y Combinator’s podcast. Today’s episode is with Brian Donohue. Brian’s President of Instapaper and a Product Engineering Manager at Pinterest. You can find him on Twitter @bthdonohue. Alright, here we go. Alright Brian, Instapaper has a very curious lineage and history. Could you just explain that?

Brian Donohue [00:00:25] – Sure. Instapaper was started by a single guy named Marco Arment, and he built the entire product and service and operated it from 2008 to 2013. Marco, beside Instapaper, was previously known for being the CTO of Tumblr and Instapaper was kind of his side project that he worked on while he was at Tumblr. My impression was he would work nights and weekends. He eventually launched this thing. It had quite a bit of fanfare early on, even though it was just a bookmarking service at the time.

Craig Cannon [00:00:59] – Yeah, but it was early days App Store?

Brian Donohue [00:01:01] – This is even pre App Store. We’re talking January 2008. Marco launches this bookmarking service called Instapaper, and it’s essentially just a website and a bookmarklet. You could save articles using a bookmarklet, and all it was was a website. Coming into like March or April 2008, he launched the reading mode for Instapaper using its text parser. The test parser would take an article from a website, extract just the text and the images and provide just the reading view and experience. If you’ve used Instapaper, you’re pretty familiar with this, it’s one of the core value propositions. Then in August 2008, he launched, with basically the App Store launch, he launched Instapaper for iOS, which leveraged the bookmarking service and the text parser to kind of create Instapaper experience that kind of we’re familiar with today. It was the first time where you had this combination of bookmarking experience, this text parser that would extract the important parts of articles, and then also the mobile application where it was kind of all the articles were saved offline and kind of available to you wherever you were. In the early days of Instapaper in that 2008 App Store world, Instapaper solved three key pain points, consumer pain points. The first one was, if you remember early iPhone days, the early mobile networks were really slow, and it was impossible to load a website. You’d be waiting forever, things would come in pretty progressively, and then when it did load,

Brian Donohue [00:02:38] – it was impossible to view the content because there was no such thing as the mobile web. You’d pinch to zoom and try to zoom in on this column and then you’d be panning around and it was like this really weird experience. The third thing was that the iPhone was kind of primed to be a reading device because it was always with you, but for a lot of reasons it was not really a good reading device because there was no good reading applications, the screen wasn’t really good. Instapaper comes along and it lets you save articles, the articles are perfectly formatted, you can sync the articles while you’re on wifi and then access them from anywhere. It solved… And then also back in the App Store days in 2008, there were not a lot of really useful mobile applications. There were like, a lot of iFart apps and things like this. At the time it came it was pretty revolutionary and solved a lot of pain points. And as such, kind of had a pretty huge addressable market, which is almost anyone with an iPhone, right? As the iPhone user base grew, Instapaper kind of grew alongside it. Now, you fast forward to 2018, most of those things are no longer problems. You have LTE networks that are super fast, the mobile web has its problems and there’s various efforts to try to solve them like accelerated mobile pages from Google, but at the end of the day, you can still load a website and read it pretty easily.

Brian Donohue [00:04:12] – Then the third one is there’s actually tons of reading applications now, and the iPhone is a main reading device for a lot of people, whether they use Kindle or Apple News or New York Times or Wall Street Journal or you use some aggregator like Reddit or Hacker News or Twitter. It’s fairly easy to read on your phone now. The market has shifted from something that had kind of like a pretty wide appeal in the early days to something that’s far more niche now, and basically the use case for Instapaper these days is you are a veracious media consumer, you use source content from a lot of different places that might be directly from publishers, it might be from news aggregators like Reddit, Hacker News, Techmeme. It may be from social like Twitter or Facebook, and you essentially need a place to stage all that content temporarily until the time that you have enough time to kind of read it in bulk and go through it in bulk. The market size for that is fairly modest and that’s part of the reason that both Pocket and Instapaper wound up landing at larger companies back in 2016 and Readability wound up shutting down, because actually I think the market appeal for that product is fairly limited and it’s not one that’s massively growing over time.

Craig Cannon [00:05:38] – Did you notice, when Safari launched the Reading List, a decrease in users?

Brian Donohue [00:05:43] – When that happened, I believe it was 2011 or 12, I wasn’t involved with Instapaper at the time. I haven’t looked at those historical trends to see if that was the case. It’s not just Safari, it’s actually a lot of applications. Save for later became a feature of a lot of things. YouTube, New York Times, Wall Street Journal, Safari, all these things have like this Reading List, save for later. I found this thing and I want to come back to it but I don’t have time right now. All of those things kind of chip away at kind of like the usefulness of this core service, and there is a large user base who’s still using it daily, weekly, monthly. It’s been kind of a big privilege for me to have the opportunity to service those types of people.

Craig Cannon [00:06:36] – BLet’s go back to the intermediate time between the creation and now, because Instapaper’s story’s particularly interesting. Talk about the time how Betaworks acquired it.

Brian Donohue [00:06:48] – Sure. The story that I’ve heard, and I joined Betaworks shortly after the acquisition and joined the Instapaper founding team, the Betaworks’ Instapaper founding team. The story is that Marco wakes up at two in the morning, he’s a little restless, he’s trying to figure out what to do with Instapaper. There were a couple of factors there, a couple of reasons why, and I haven’t talked to Marco about this directly, so this is kind of my hypothesis, but I think one was Marco was probably interested in working on some other projects like Overcast, which is his current podcasting service. It’s mobile app and service that he runs. In 2012, and so the timeframe for this is late 2012, in April 2012 an important thing happens in this history, which is Read It Later Inc., which was a read later company originally for Firefox, built for Firefox, bulk mobile apps and so on, they wind up relaunching and rebranding as Pocket. This is April 2012. In doing so, they one had raised a lot of capital, they had several engineers working on it, and they had launched iOS and Android applications for free in the App Store. Now, Instapaper had no Android application, and the iPhone app was $3.99 to download. In relaunching Pocket in 2012… I’ve looked at the downloads for Instapaper, and they just start tanking after April 2012. You have this dynamic where you have this service that’s really strong, but there’s a free competitor that’s also really strong,

Brian Donohue [00:08:43] – and people will always seek the free competitor. The combination of fatigue from running the service and Pocket launching as a free application in 2012 led Marco to rethink what he was doing with Instapaper. The story is he wakes up at two in the morning, he creeps downstairs, he’s trying to think about what to do with Instapaper, he reaches out to John Borthwick, who’s the CEO of Betaworks. John Borthwick and Betaworks had invested in Tumblr in the very early days, in their seed round. John Borthwick had Marco Arment come to Betaworks and talk about mobile app development, so they had a good relationship there already. Marco basically said to John, I’ve been thinking about what to do with Instapaper. I’ve been thinking about a longterm home for it, and I think Betaworks could be that home. They eventually worked out a deal where Betaworks would have a majority share of Instapaper and Marco would retain some ownership in Instapaper and continue to act as an advisor. The understanding was that Betaworks would continue to invest in Instapaper, staff a team around it and continue to build it. That was announced in April 2013, and so you figure that probably took about four months from December 2012, which is my understanding of the timeline.

Craig Cannon [00:10:06] – At which point you get hired by Betaworks to run it. Then you run Instapaper within Betaworks for a couple years, and then how did the Pinterest thing happen?

Brian Donohue [00:10:17] – I think we should just back up a second. I was hired in July 2013. I was not hired to run Instapaper, I was hired as an iOS developer for Instapaper. I had started a company, the company had never got more than a few thousand people to sign up for it, it was a location-based social networking company. I started in 2011. By 2013, it was really not working. I had gone to Betaworks for an investment, and they had said we’re not interested investing in this space, but we really like you, and we want to work with you, and it doesn’t matter if it’s next week, a month from now, six months from now, a year from now, just keep us in the loop, let us know how it goes, and we’d love to have you here. When the company folded, I went to Betaworks, I was like, “Look. Need a job.” Actually the person I was talking to was Nick Chirls, who you know as well. I said, “Hey, I need a job.” The opportunities were Done Not Done, which got shuttered within a few months of my joining, this gif search engine called Giphy, which I was like, gifs? That’s like from the ’90s, like this is crazy. But I do wonder what that road would’ve looked like if I had taken that one. Then the third one was Instapaper, and Instapaper was this pretty prestigious application that was like, a long time in the App Store. I had used it in the past. I was kind of interested in it. I interviewed for that job. I joined as the iOS developer, and a lot of the skill that I had from starting a company and that perspective had carried over.

Brian Donohue [00:11:59] – There were a lot of gaps in terms of who was writing blog posts, who was doing the marketing, who was building product strategy, and so on and so forth. I just slowly started to pick up some of those things, and there’s a whole story about how I became into the leadership position, but I don’t know if you want to go into it?

Craig Cannon [00:12:16] – Yeah, yeah absolutely.

Brian Donohue [00:12:17] – Essentially what happened is even in my first interviews, I had said to the person running it, who was a Betaworks partner named Andrew McLaughlin, I said to him that I did a competitive analysis across Instapaper, Pocket, Readability. I had said to Andrew that I didn’t think Instapaper could compete as a paid application in the market with strong free competitors, it just didn’t make any sense.

Craig Cannon [00:12:43] – Now at the time, did they have a subscription model after the paid? Were they doing like freemium?

Brian Donohue [00:12:49] – Pocket? At the time, Pocket was totally free.

Craig Cannon [00:12:52] – Okay, for everything, every feature.

Brian Donohue [00:12:53] – Everything was free.

Craig Cannon [00:12:54] – Okay.

Brian Donohue [00:12:55] – I think Readability was the same. You had Instapaper, which had a $3.99 app download in 2013, and going back in time it had actually been more expensive. And then also $1 per month subscription for search functionality. It had this full text search feature where if you had saved an article about Obama, you could search Obama and it would surface the article, even if it wasn’t in the title. Even in that early interview, I basically said Instapaper should be a free application, and as I was hired, I kind of advocated for this direction. There was a lot of pushback from it from Betaworks leadership, where because the app downloads were 40 to 50% of the revenue from Instapaper, there was a lot of hesitation around just eliminating it. What I did is I had been in touch with a representative at Apple via one of their eduction programs, and I told her that we were interested in having Instapaper participate in free app of the week. Free app of the week is a program that the App Store runs where they take a paid application, they make it free, they put it right in the front page of the App Store, or what used to be the front page of the App Store, and give it a pretty prominent treatment. Couple weeks later, she got back to me and said there was a slot that was sometime in December 2013. Basically, I had gone to Andrew, who was running Instapaper at the time, and I said listen, we have this opportunity to do free app of the week,

Brian Donohue [00:14:34] – I want to test the hypothesis of making Instapaper free. What I’d like to do is give a two month free trial to Instapaper subscription for everyone who signs up during the free app of the week trial period. I want us to measure how many that we convert after the two months. What I want the hypothesis to be is to see if we can continue to build the business by transitioning from a paid application with a subscription to a freemium application. We had a couple chats, we eventually went through with the free app of the week, we executed on this plan. In that time, in that one week period, we had more app downloads than we had an aggregate over the past two years. We increased our subscriptions by 10 to 15%. We basically had it so that three weeks before it expired, there was a little notification that came up in the app, and then like, a couple days before it expired there was a notification that went up in the app saying like, your free trial’s going to expire, consider subscribing.

Craig Cannon [00:15:38] – What did that percentage breakdown of new users, how many subscribed?

Brian Donohue [00:15:44] – The way this worked was interesting. We had over a million downloads. Of the million downloads, I think only 650,000 people created accounts, meaning that people downloaded it and just–

Craig Cannon [00:15:58] – Can you use it without an account?

Brian Donohue [00:16:00] – No, so they never opened it. Or they opened it and were like, forget it. So you do have to create an account to get the experience. Then of those people, many turned out. I think we retained maybe 15% of them. Then of the 15% we got some of them became subscribers, I don’t want to talk any of these numbers because you can work out the percentages. But we had a 10 to 15% increase in our subscription base. Basically what it proved is that, I think it proved a couple things. One is that the paid app download was a major cap in our growth, and that we were not able to compete in a market with strong free competitors as a paid application. And that two, when people used the application, we could convert them in a pretty predictable, reliable way, and that they would convert and see the value once they started using it. What I had proposed, and this is January 2014, basically after we executed this successfully, John and Andrew were like, you can be the general manager. I set out the plan for 2014, and the plan was pretty straightforward. It was make the application free and by the first step was creating more features for the subscription package, and then increasing the price of subscription from $1 a month to $3 per month, and then making the application free. Over the next eight or nine months, we built highlighting, and then we capped highlighting, so you can make I think five or 10 highlights per month, but after that you needed a paid subscription. We built text-to-speech, which we offered for free

Brian Donohue [00:17:43] – but we had a playlist feature, where you could select multiple articles and do text-to-speech, and that was paid. We tried to strike this balance between the free aspects of the feature and kind of like the more pro and what you would have to pay for. Then we did a couple of other small things and then in September 2014, we made the application free and launched the new subscription pricing. We did that across iOS, Android, and web. Then after that I was promoted to CEO and the leadership position. And that’s kind of how I went from like, the iOS guy into the leadership position. We took a pretty big hit, I think which was expected, on the revenue side for a couple months. But within six to eight months, we had recouped what we had lost on the monthly revenue, and we were actually back into a growth trajectory, which was awesome to see. Then a lot of my focus moving from that late 2014 to mid 2016 when we sold it to Pinterest was getting kind of the business fundamentals right, making sure that we had control over our costs, and as we continued to grow our revenue, hit a place where we were break even and profitable. That was kind of my main goal moving through 2016. Then, so I think that’s kind of, caps out.

Craig Cannon [00:19:11] – Well that’s as much as I know. Sounds right. Do you know what motivated the acquisition interest from Pinterest?

Brian Donohue [00:19:20] – Yeah, so we had fielded some interest even going back in 2015.

Craig Cannon [00:19:26] – From them?

Brian Donohue [00:19:27] – From other companies.

Craig Cannon [00:19:28] – Okay.

Brian Donohue [00:19:30] – There were two large media companies in New York and one media company on the West Coast. One of the large New York media companies sent us a letter of intent for a large sum, very large sum. It was in the eight figure range. It was big. We were like, you know, we were at Betaworks and we were talking about it and talking about like, the longterm prospects of Instapaper and whether or not this made sense, and I think everyone felt like this was a good outcome, at least for the shareholders. I think sometimes you think about the people who use the product, you think about the employees, and you think about the shareholders. Unfortunately in technology, the motivations of each of those groups are usually very different, or sometimes very different–

Craig Cannon [00:20:20] – And not always clear.

Brian Donohue [00:20:21] – And not always clear. What’s great now with the new incarnation of Instapaper since we’ve spun it out of Pinterest is those things are very in line. I think we should spend time talking about that. But I think in this case, the motivation was largely around the shareholders. We went ahead with this letter of intent, we did all the diligence with these people, I did deep tech diligence with these people. There’s a picture on my Instagram from back in 2015 where I’m sleeping at my desk with my feet on the desk. Someone took a picture of me, and I remember it was like I had just launched a big app update, and done all this tech diligence and I was exhausted, I was just wiped. Then I think we had an eight week quiet period where they were doing diligence and so on and so forth, and in week six they pulled out because of a strategic change in direction, and it was really rough. I remember it was actually Halloween 2015. I actually remember it really well, because I remember getting pulled into a conference room, being told they backed out and that was that. I went out and got pretty drunk that weekend, I was just like, trying to take my mind off of it. I felt okay about it until the Monday I got back to work and I was like man, I have to actually like, build this company again, I have to like– I was in the mode where like, alright, we’re going to do this thing.

Craig Cannon [00:21:54] – It’s tough, like you get all of your emotions tied into it, you think it’s going to be a big change, at the least a new chapter, and then you’re just back again.

Brian Donohue [00:22:01] – Yeah, and not to mention the significant amount of money that would’ve been–

Craig Cannon [00:22:05] – Yeah, that’s helpful.

Brian Donohue [00:22:06] – There were a lot of things where you were on a certain trajectory there, and I was like, I don’t know, I was like, looking at houses to buy–

Craig Cannon [00:22:15] – Oh wow, you really got into it.

Brian Donohue [00:22:17] – In New York! I mean, I was like, it was, it seemed like a done deal. I was going to put a down payment on a place in like, Gowanus or in South Brooklyn somewhere. Then it was just like boom, done. Now you’re back to where you were. It was hard, too, because the whole team knew about, the whole team, there was like three or four of us, but still, I mean it’s kind of rough to go back to everyone and be like, “Hey, by the way, this isn’t happening anymore.” I was pretty deflated, I think as you might expect. We went back to the other large media company, the West Coast media company, and started those conversations again. Pinterest had been talking to Betaworks separately about things. Their corp dev had been talking to Betaworks. They mentioned that they were interested in news. We had a meeting with our corp dev. I had a meeting with Andrew and the guy who was running corp dev at the time. I didn’t think the meeting went particularly well. I was kind of like this feels like a waste of time, I don’t know why we’re doing this, spinning out new conversations, whatever. Then eventually we got connected with the head of products at Pinterest, a senior PM at Pinterest. There was some connection with Andrew and the senior PM from the Google days, so they knew each other and were very friendly. Then we continued talks with them, but these initial talks were in December 2015. The acquisition happened, signed and done, in August 2016, so you’re talking about

Brian Donohue [00:23:56] – a nine month process. It wasn’t all on, I mean it was like, we had talks and then it cooled off, and then we came back, and then there was a negotiating period or whatever. Just to kind of illustrate I mean, from the time that we fielded initial acquisition interest until the time that we sold the company was over a year, it was 13 months. These things take a fairly long time, and you may have a party that’s interested and pulls out. I learned a lot from the whole process.

Craig Cannon [00:24:29] – Psychologically, for someone in your shoes, what do you tell them at this point? Don’t look at houses until you have a check? How do you manage the psychology of it?

Brian Donohue [00:24:44] – I would say definitely don’t count your eggs before they hatch, right? I mean that’s the expression. It’s tough when you are so close to something. I mean we were all like, when we signed this LOI, we were like high fiving and stuff. I was under the impression it was a done deal, and to back out of an LOI is, from a business perspective, usually they’re nonbinding but it’s pretty frowned upon and it can damage your integrity and your reputation and so on and so forth. Typically it’s not done. I learned later on that you can add breakup fees to these, and so I didn’t know a lot about this stuff, and this was my first time going through this process. You can basically say if you do pull out, you have to pay X. That can kind of disincentive them from doing all this work. Then I think also in the pullout, there’s some other issues. It sends a signal to the market like maybe something is wrong, when that definitely wasn’t the case. But managing psychology, I mean, it was definitely a roller coaster. I would say you have to be very calm, collected. Don’t shop for houses until the money’s in the bank. Because there’s no point. I just try not to get too down on the downswings.

Craig Cannon [00:26:16] – But then ultimately you landed at Pinterest, moved out to California, you got soft. How’s that going?

Brian Donohue [00:26:24] – It’s good. Betaworks is in New York, I’m from New Jersey, I grew up in the New York area. As part of the deal, it was understood that we would all be moving out to Pinterest. And when I say we all, it was three. There was me doing all the engineering and all the leadership piece. There was someone doing customer support, maintaining the parser, doing kind of a variety of other things, marketing. Then there was a designer. Of the three of us, two moved out to Pinterest, the designer decided to go do something different.. And how’s it been? There’s a big difference between New York and San Francisco, and it’s not something I want to get into necessarily on the podcast. I’ve gotten really into hiking and all the outdoor stuff, I think you’re kind of into that, too. That’s been awesome. Working at a large Silicon Valley company has been awesome. I’ve learned a ton about building products at scale, processes for doing that, even just some of the methodologies that are used are vastly different than what I’ve been exposed to at smaller scale startups. I think of kind of my career as the scale at which I’ve shipped software. In the first company I started out of college had no customers. We just demoed it a little bit. The company I started after that, we had 6,000 people sign up for it. Instapaper has millions of registered users, and Pinterest has a quarter billion monthly active users. That’s kind of how I think about the career trajectory of building software. When I started at Pinterest,

Brian Donohue [00:28:09] – a lot of the initial work was around doing Instapaper integrations. We did a variety, which we can talk about. Then once I completed those integrations, I started doing a lot of Pinterest-specific work versus individual contributor software engineer. Now starting this year in January, I have been managing a team of engineers building a new feature of Pinterest. I’m managing a team of eight very talented software engineers who are great and I care about very much. I’ve learned a ton about managing in a larger company.

Craig Cannon [00:28:50] – I’m curious about how it’s gone managing it within Pinterest. We had Courtland Allen from Indie Hackers on the podcast a while ago, and now that’s within Stripe, and that’s been an interesting process for him. For the most part it’s been good. He’s been able to get off the gas in terms of raising the sponsorship money and just focusing on the community and the forum and the content. How has it been for you and how do you manage that thought process while you also have a job working on product at Pinterest?

Brian Donohue [00:29:22] – In late 2016, we were at Pinterest, we did the acquisition in August. Around November, December, we had a conversation with Pinterest leadership about some options and directions for Instapaper in 2017. I think presented like four or five options. One was staffing a whole team around it and treating it as a business unit and trying to grow it. The second one was staffing some data science around it and seeing what kind of news based insights we can get on an aggregate basis, and so I was always pretty adamant about not sharing personal data in any way, shape, or form, but aggregate information about the number of saves on a URL might be interesting, might help the powers and features within Pinterest. The third option was to put it in maintenance mode and just kind of have me and Brody and the other person from Instapaper maintain it. That would be kind of more on the side in doing that. And then the fourth option was shutting it down. That was something that we discussed. I felt that it was pretty low investment to keep it running and that there would be a lot of upset people if we shut it down, and that it didn’t make a lot of sense when we had people willing to do it and we could do it in a sustainable way. It was an option, but a non option kind of. It was like we tried heavily to steer away from that. They asked me for my recommendation. My recommendation was to put it in maintenance mode at the time and just treat it as

Brian Donohue [00:31:01] – a side thing that I maintained. The reason being is that treating it as a business unit, I just felt that every dollar put into Instapaper could maybe return 70 cents, a dollar, it would be pretty challenging to have it kind of be an investment that had a solid return. But I felt pretty strongly that every dollar into Pinterest would give a $1.10, $1.25, $1.30. It didn’t seem to make a lot of sense to put tons of resources into Instapaper when there’s so much work to do on Pinterest, and that there was much more reliability for getting value out of the work done in Pinterest. Then on the data science we talked about it a little bit and decided I would just do most of that work myself. We got some agreement that we would kind of keep it in the maintenance mode. Then essentially, I dedicated three, four hours a week to Instapaper and regularly launched new app updates and fixed the servers and do things like that, but large parts of my focus shifted to working on Pinterest.

Craig Cannon [00:32:11] – I forget when you told me you were going to spin it out, but at what point did you guys decide you’re like, “You know what? We’re going to take this thing on its own again.”

Brian Donohue [00:32:21] – Sure. We had that conversation late 2016 through 2017. We did a variety of updates. Starting in early 2018, so this year, I was thinking a lot about Instapaper, longterm trajectory. It felt to me that given the current course, it would be on a path for shutdown. Just like, drawing out things, and I think all things in life have a certain trajectory. That could be people, businesses, products, so on.

Craig Cannon [00:32:50] – That’s the sad reality of a lot of these things that get acquired by big companies. They have, I mean obviously not a tremendous amount of users that love it, but some amount of users that love it, and then they just kind of die quietly as people get promoted or buy a house somewhere and leave and go to another company. It’s interesting that you’re like no, we want to keep this alive, let’s take it.

Brian Donohue [00:33:14] – It is interesting. There’s a couple reasons why we were able to make it work. Just to touch on what you said, though, a lot of people were angry about the Pinterest acquisition. A lot of people on Hacker News, as opposed to say, people were are listening to this podcast, were angry about this acquisition. They had seen a lot of applications that they love go by the wayside and very similar things. Whether it was Mailbox or Dropbox or Sunrise with Microsoft, or Parse with Facebook. I mean, there were tons of these things that were these really beloved applications that had a cult following and a lot of users and they got bought by the big companies, they’re no longer kind of in line with the mission of the original thing, they get integrated or shut down or whatever.

Craig Cannon [00:34:04] – Right, turned into open-source or something.

Brian Donohue [00:34:06] – Exactly. The reason we were able to make it work for Instapaper is Instapaper was always run by a very small team. I’ve always felt that with our existing user base, we can monetize and cover costs. I think a lot of these things, like some of the ones I just mentioned, they require lots of engineers, they require lots of upfront capital. And they basically need to continue to have these seeds pump more money into them and continue to grow so that they can eventually become self-sustainable. But they’re not self-sustainable usually in the forms that they were acquired in. In the case of Instapaper, it’s very different. It was built by one person, ran by one person for a long time. When I came there were three or four other engineers. As they left, I picked up backend responsibilities, Android responsibilities, website responsibilities, and I basically got to a point, and I think a lot of people think Instapaper is like a big thing with a lot of people. Basically from late 2014 through now, I’ve been the person doing all the backend engineering, all the iPhone engineering, Android was started in 2015. But it’s basically just been me doing all this stuff. Because of that, I can reduce kind of one of the largest costs in a company, which is the human cost, right? In doing so, I was of the firm belief that we could cover our server cost with the existing usage and with a reasonable conversion rate on the existing usage. I had the benefit of looking back at

Brian Donohue [00:35:56] – a lot of the historical data on how many subscribers we had, what the growth rates looked like, and so on and so forth. I just felt like this was the type of product that could continue for the foreseeable future. I knew that it wasn’t ever going to map to a Pinterest top line metric, or KPI or OKR or whatever you want to call them. Basically in early 2018, I emailed the CEO of Pinterest, Ben Silverman. The subject said Instapaper, and I just said hey, can we chat? I basically had a conversation very similar to what we just discussed, which was that it felt like the current trajectory was for shutdown, I didn’t feel good about that, I didn’t feel good about taking away this product from the many people who use it just because it didn’t map to some top line metric or OKR, KPI, that it had been my privilege to serve these people and I wanted to continue to serve them for the foreseeable future, and that I thought the two ways we could put Instapaper back on a trajectory where it could survive for the foreseeable future is to either treat it like a business unit within Pinterest, which I said my recommendation was the same recommendation I made in late 2016, which is that that doesn’t make sense. Or we can spin it out into an independent company. We talked a lot about it. As part of the discussion, we agreed that it would be a handshake understanding that this did not mean I was leaving Pinterest. The only thing that would change here is the ownership of Instapaper. Now that Instapaper is spun out,

Brian Donohue [00:37:45] – I run it in a very similar fashion I was at Pinterest. I dedicate my nights and one day on a weekend per month, and I fix all the issues, launch new app updates and so on. I am trying to build Instapaper into a thing that can sustain itself for the next 10 years. It’s been around since January 2008. Celebrate our 10th birthday in January. I want it to be a thing that can last for another 10 years.

Craig Cannon [00:38:16] – That’s awesome, man. You did raise a little bit of money now that it’s spun out, right?

Brian Donohue [00:38:21] – Yep.

Craig Cannon [00:38:22] – So what were the terms on that? What are the expectations on that?

Brian Donohue [00:38:24] – Sure, sure. So we raised $80,000 from friends and family, and a very ragtag like, six people. To kind of give you the average size, I think the largest check was from me, which was 13,000. Then most of the people had 10, some people put in five. The pitch was interesting because our express purpose is not to try to grow this into a huge thing and exit or do anything crazy. Our thing is to make this a longterm type of business, and again, trying to align what our customers want, which is they basically want the service to last forever I think, right? What the operators want, which is again, just to kind of make it so that this is a longevity thing. Then kind of aligning with the shareholders, the shareholder pitch there. Essentially what we said to shareholders was we structured it as preferred shares. We basically said that we’re going to sell you preferred shares at this price, and your preferred shares will automatically convert to common shares when we give you back 125% of your investment. Basically what we’re saying is we’re going to have a 25% increase on your investment, and we’ll automatically convert them from preferred to common shares, and then after that any dividends to investors would be done across the normal common share equity split. Yhe pitch to them was that you have this 25% return on your investment–

Craig Cannon [00:40:06] – Any time frame, just open?

Brian Donohue [00:40:07] – We said within a year. Based on current trajectory it looks like maybe more like 16 months we’ll be able to get there, maybe 18 months. And then on a yearly basis, if we can afford to do a small dividend, we’ll aim to get you 10% monthly investment return. Sorry, yearly investment return, return on your investment. And so there was some risk up front here, but I think all the people who were involved, there were like a lot of ex-Betaworks people, my aunt put in money, so it was very friendly.

Craig Cannon [00:40:43] – Right, and not life-breaking amounts of money.

Brian Donohue [00:40:46] – Very small amounts of money. There’s some risk, but I’m happy to kind of report that things are going very well, that we do have a lot of people who are converting to Instapaper subscriptions. We are now cashflow positive, which is great. Couple thousand dollars. A lot of that was around significantly reducing our server cost, I did tons of work around that. But also just continued growth in the subscription offering. One thing that I am trying to piece together is that a lot of the subscription offerings, a lot of the new subscribers are yearly subscribers, and so we need to basically count for that revenue as we realize it. There’s an accounting practice called deferred revenue, so while we’re cashflow positive, I don’t know how we’re doing against our deferred revenue and we want to do accounting on a deferred revenue basis, meaning that we would realize the revenue from the yearly subscriptions in each month that we actually offer the service. If you subscribe for a year in August, then when you recognize $3 in August, or 30 divided by 12, and then the rest throughout the rest of the year. We’re cashflow positive. I still need to figure out on a deferred revenue basis how we’re doing as a business, because we need to spread that money over the whole year, pay for several costs–

Craig Cannon [00:42:10] – Right, make any kind of prediction.

Brian Donohue [00:42:11] – For those people over the year, we’ve been now this is our third month in business, we’re starting to set up books and do things like that. Still early scrappy days of the new Instapaper.

Craig Cannon [00:42:24] – This is cool, man!

Brian Donohue [00:42:25] – Yeah.

Craig Cannon [00:42:26] – You got some questions, too. Let’s see if there’s anything that are specifically Pinterest-related. Alright, so yeah, let’s do this one from Jiro, who it sounds like you know. What types of product integrations could Pinterest have done with Instapaper?

Brian Donohue [00:42:43] – Yeah, so there were two main ones that we talked about. I touched on one, which was taking the aggregate signals from URLS from Instapaper. How many saves we got, how many reads we got, how many likes we got. We essentially score those for Instapaper and that powers a feature called Instapaper Daily. Each day of Instapaper Daily gets rolled up into a weekly email called Instapaper Weekly. It’s kind of like the best article saved every day.

Craig Cannon [00:43:10] – Do you name all this stuff? You’re crushing it with the names.

Brian Donohue [00:43:13] – The products?

Craig Cannon [00:43:14] – Yeah, I’m kidding.

Brian Donohue [00:43:14] – So the Daily was, I think I named the Daily and the Weekly. The Daily was more a group effort, the Weekly was just kind of an obvious one. We talked about doing like a monthly thing, too.

Craig Cannon [00:43:24] – What are you going to call it?

Brian Donohue [00:43:25] – The Monthly.

Craig Cannon [00:43:26] – Oh, nice!

Brian Donohue [00:43:27] – That was the idea, yeah.

Craig Cannon [00:43:28] – Yeah, great.

Brian Donohue [00:43:28] – Pretty self-describing. Essentially we score those using something called Instarank, which is done by one of the Betaworks’ data scientists, and we essentially took all the URLS and scores from each day for Instapaper and we made them available to Pinterest with the idea of having some news based feature within Pinterest. I think one that was interesting is I looked at the interest section between URLS that we saw on Instapaper or we had signal on on Instapaper, meaning that there was some saved read like, in a given day, and then compared those to the URLS that were in Pinterest in each day. What I found is that on the first day that we saw those links, only 16% of those links were in Pinterest. We actually see a much different set of URLs on a given day. And then over time, I think within seven or eight days, Pinterest gets to like, 60, 70, 80% of the links that we’re seeing. There’s still different set of overlap there, but given the nature of the types of links that Instapaper has, which is very news based, and the types of links and the experience that we were looking to build within Pinterest, which was like some sort of news based recommendation system, by the time Pinterest gets to those links, a lot of those links are out of the news cycle. It’s kind of, the data’s difficult to use. We built some experiences around integrating those signals, around having ranking recommendations for news articles using those signals, but there were these big gaps where it took time for these to make their way onto Pinterest.

Brian Donohue [00:45:16] – Whereas on Instapaper, we kind of have all these people distributed on the internet who are saving this stuff to their accounts and doing it very fast as the news breaks. And so that was one reason that product integration I think didn’t work. I think Pinterest is also this algorithmic recommendation engine that’s heavily based around things that are kind of more longterm evergreen, like recipes, fashion. Fashion has cycles, but home decor. Whereas there’s a much different cadence for news, right? It kind of changes like the way we do recommendations.

Craig Cannon [00:45:53] – Wait, so were a lot of people just saving short form news articles to Instapaper? Is that common? I would just assume you would read those and then anything that’s long you would actually save.

Brian Donohue [00:46:05] – There’s two big use cases for Instapaper. There’s the long form one, which I think is what you’re describing. But there’s also the like, “I want to be able to find that stuff again.”

Craig Cannon [00:46:15] – It’s more of a searchable archive?

Brian Donohue [00:46:17] – Yeah.

Craig Cannon [00:46:18] – Yeah, okay.

Brian Donohue [00:46:18] – People will save things that they have read, and I do this too, I save even pretty small things, like I’ve saved things like campfire recipes, so if I go backpacking or camping somewhere, just so I can kind of get to it really easily, and it’s offline, which in nature you might be offline. Those are the two key use cases. I’ve had a lot where I’ve read this article about startups or entrepreneurship or whatever and I wanted to recall it and get the thing back, like pull up the article again. Doing a Google search, sometimes it’s like, you’re like I can’t remember which blog it was on or so on and so forth, but it’s much easier to do if you have kind of your own personal search index. If you subscribe, plug for Instapaper Premium, you can search through all articles you save and get a full text section. We do get both and we do get kind of a different cut versus what Pinterest gets at least on day zero, which is when that recommendation is most important. The only other thing that we kind of looked into was kind of doing an offline reader mode for Pinterest. For various reasons, like at the scale of Pinterest and so on and so forth, it would be very difficult to do that. People save a lot of things on Pinterest, and I think the expectations are a little bit different. People expect that all their Instapaper stuff will be available. If we built that expectation for Pinterest, we’d have to store like, tons and tons and tons of stuff.

Craig Cannon [00:47:53] – Yeah like video, massive videos, yeah.

Brian Donohue [00:47:55] – Just so much more content, because the nature of the service is actually very different. It’s something we discussed, and actually when we were talking about spinning it out, we discussed like maybe this would be a place of value. I talked to the head of product about it, and I said like, there’s so much stuff that is important for Pinterest right now, and this seems like the type of thing that seems like a nice idea but will be infinitely deprioritized behind the many other more critical things we need to do. I don’t really see that as something that’s viable. Are you going to staff people to do this project? And he was like, no. And so I said yeah, because it doesn’t really make sense to do–

Craig Cannon [00:48:38] – Yeah, and like all those super technical features, it’s funny, like I think about Overcast in this way. Overcast, I don’t have the numbers, but it seems to be very highly adopted among nerdy people who want crazy granular control over notifications per show, offline downloads per show, but the average person doesn’t care at all. For Pinterest, focus on that seems….

Brian Donohue [00:49:02] – Instapaper is actually very similar. I wouldn’t describe them as nerdy, I would say they’re very, there’s a community of people who are very particular about the features that are in a product, they want massive control over the features in a product, they’re very privacy focused. Marco has built a large audience of these people, right? So I think what’s cool about Marco is that he has his audience, and so when he launches products, he launches them directly to this audience, and they typically go and they download, buy, subscribe, use the products that he builds, and they do it because Marco is the same type of person who wants kind of that control, those privacy settings and so on and so forth.

Craig Cannon [00:49:45] – He’s a great model. It’s very cool. A lot of people look up to him. So got some silly questions in here. Alright, here we go. Ryan Hoover from Product Hunt, he asks, “I’m curious how he and the team,” very small team, “balance simplicity with new feature development and product expansion.”

Brian Donohue [00:50:07] – This is a really good question. We’ve built basically our product roadmap always historically based off of user requests, so people that write in. We track all those user requests and essentially we build a model based on the most requested features. That’s always a big thing. Even going back to 2014, when I got put into the General Manager role for Instapaper, I built this little table, this three by three table, and the things that I want to evaluate features on were did users request it, does it give us a competitive advantage, can we build it into the business model? Then evaluating all of the features based on that, and we’ve essentially built our roadmap based on what users want, thinking about monetization a little bit, and then also does it give us a competitive advantage. A lot of the features that we’ve been requested are very power user features. People want to do highlights, they want to create annotations, they want to be able to export all their highlights and annotations to a third party service like Evernote or something like that.

Craig Cannon [00:51:14] – Or the amazing, Kindle Dot Amazon.

Brian Donohue [00:51:17] – Exactly. I think actually a lot of people want to take all their highlights and put them into one place. There’s this notion of like a common place book, where like all your learnings are kind of in one spot. I know Ezra Klein, who’s the editor in chief of Vox, uses Instapaper to Evernote and then puts his Kindle highlights in Evernote using some service, I think it’s called Together he kind of has them all on Evernote.

Craig Cannon [00:51:43] – Again, it’s like this searchable memory bank.

Brian Donohue [00:51:45] – Exactly, of all the things that he reads. And so many of those features are very power use features. Some of the other ones are speed reading. Text-to-speech, again, people use Instapaper in their car while they’re driving, right? So they’ll put the playlist on and just go.

Craig Cannon [00:52:03] – Use the iOS speech to text, or text-to-speech?

Brian Donohue [00:52:08] – Yeah.

Craig Cannon [00:52:09] – Default.

Brian Donohue [00:52:10] – We use the speech synthesizer. There are a couple new iOS voices that are really great. There’s one called Samantha that’s really high quality, and the one that most of our users request is called Alex. Alex I think is like a couple megabytes download, but you can kind of go into the voices in iOS settings, and if you have that downloaded, we can detect it and use that by default. Our strategy here for building that is to keep the product really simple for the majority of people. It’s already a pretty complicated product, where it’s like, “Okay, you’re going to use this thing but you’re going to find stuff elsewhere and the put it in here and then come back to it.” It’s already overly complicated.

Craig Cannon [00:52:49] – The browser extension’s like, “Whoa!”

Brian Donohue [00:52:51] – You got to install this here and then, it’s a challenge. And so our strategy for simplicity with new feature development, and it’s not a great strategy, is we just hide all the features. We put them kind of in hidden places, and I think our idea and our philosophy behind it is the people who want those features are going to go out of their way to go find them. We don’t care about moving metrics on specific features or whatever, what we care about is the overall product and keeping it simple. Most of those features like text-to-speech and speed reading, if you go into the reader view, you press the share button, they’re in the bottom sheet there, and they may be kind of pushed back based on what other things that you have there and what you’ve configured. If you scroll on the bottom sheet, you can get to the text-to-speech or the speed reading features. Many people don’t know they exist, I think there’s a question–

Craig Cannon [00:53:46] – I didn’t know it existed.

Brian Donohue [00:53:47] – There’s a question on here that says can Instapaper be voice enabled? So we can–

Craig Cannon [00:53:52] – Yeah, yeah, yeah, we can cross that one out.

Brian Donohue [00:53:52] – We can cross that one out.

Craig Cannon [00:53:54] – So that’s a yes.

Brian Donohue [00:53:55] – That’s a yes.

Craig Cannon [00:53:56] – But there was one, Raymond Dirk asked about the speed reading. “I love rapid reading mode, but would also love a voice enabled mode where the Google assistant or Siri reads it. Speaking of, I’d use it on my Google Home to listen to news, if that were–“

Brian Donohue [00:54:11] – We do have a voice enabled mode for text-to-speech. I think the home assistant one is interesting, and so I looked into creating Alexa skill for Instapaper in early 2016, and I think at the time it was very difficult to do because you can only pass 500 characters in a response in an Alexa skill at a time. Now, Amazon has more recently launched Amazon Polly, which kind of has some of the Alexa functionality for developers on AWS. More recently, Pocket has done an integration of Polly. They actually send articles to Polly, and I think what Polly returns is like an MP3. You can use Polly with your Alexa skill, I assume you can do it with Google Home, too. The challenge is Polly has some cost associated with it, and I haven’t done the math to figure out like, what percentage of users would use this and what the cost would be, but it might not be feasible for us to do, even with our existing premium model. Based on the volume of usage for each individual user, I’m not sure it would make sense. But it’s something that I’m still looking into. That’s particularly just for the Google Home and Alexa type of environment has that unique consideration.

Craig Cannon [00:55:35] – But I guess you could always just play it on your like, home speaker.

Brian Donohue [00:55:37] – Yeah, you could always use it on your phone and then put it wherever you want.

Craig Cannon [00:55:40] – Right, alright cool. Have you tried any of those Lyrebird type integrations where it does a straight up voice emulation?

Brian Donohue [00:55:48] – I’m not familiar with that, but we did try two different third party text-to-speech companies. There was one called IVONA, which I believe is actually an Amazon company, and there was another one we used that’s slipping me. When embedding those with the mobile application, it blew up the size of the mobile application like hundreds of megabytes, and so we looked into downloading the voices asynchronously and basically you download the app and then you download the voices separately. Kind of felt like it was a lot of work, even just actually linking the text-to-speech library just to do the functionality blew up the binary I think two times the actual download size.

Craig Cannon [00:56:34] – Does that materially affect the number of downloads you get?

Brian Donohue [00:56:38] – Only if you exceed the App Store mobile download limit. That’s changed. At the time it was 50 megabytes. I believe now it’s a hundred or perhaps more, but at the time it was 20 or 30 megs, right now it’s 50 megs. Linking these text-to-speech libraries blew it up to like 70 megs. At the time, it would’ve dropped app downloads. Now it’s a little bit easier to do on cellular networks and that the limits are higher. We’re basically looking at that, and then we have to pay for these things and trading off against this free stuff that comes with iOS devices already and we can use no problem, and it’s fairly good and probably the quality will improve over time. It was a very short lived type of experiment that we ran–

Craig Cannon [00:57:34] – Massively change the app for a short percentage.

Brian Donohue [00:57:36] – Exactly.

Craig Cannon [00:57:37] – Right, okay. Brian Kim asks, “Any growth hacks that worked well?”

Brian Donohue [00:57:45] – We didn’t focus too much on growth hacks. I think our focus has always been on delivering good products, that’s always been our best growth hack, and that’s always been–

Craig Cannon [00:57:54] – That’s the best growth hack.

Brian Donohue [00:57:55] – That’s always been basically like, when we shipped features that our users wanted that our competitors didn’t have, we were able to get more users using that. Now, I think of growth hacks in a more simple way. Growth hacks basically is when you take your product, you take a link to it, and you post it somewhere else to try to take users from another service, right? If you’re Airbnb, your growth hack is posting to Craigslist. If you’re Genius, your growth hack is making sure that your lyrics pages are at the top of Google searches for those lyrics. There’s a variety of other ones, but essentially they involve going to this other service and pulling their users. That involves kind of publishing some content, maybe their apartment listings, maybe their lyrics or so on and so forth. The content that we have on the service is saved from our users and they’re from media publishers or bloggers, and we would never republish that content, and that content is specific to that user. A lot of those types of growth hacks and tactics don’t really work for Instapaper. There is a variety of things we could do. You can publish like if you have pages of collections, so we could have some collections of articles and try to publish those. It’s just never been a big focus area for us. Probably our biggest growth hack was removing the paid download and demonstrating that that paid app download that we removed back in 2014 was a massive barrier to our growth. Today Apple actually goes out

Brian Donohue [00:59:41] – and recommends to app developers that they have subscription in their apps and they don’t do app downloads. In 2013, 2014 that was less obvious than that subscriptions were kind of a key piece here.

Craig Cannon [00:59:54] – Well it’s so much more mature now than it was back then. Alright, Gustav from YC is curious about your personal reading habits. “How do you make time for focus, catching up on everything you save, and what are your best productivity hacks related to this?”

Brian Donohue [01:00:10] – Sure. You need to make dedicated time to do this, I learned. And I honestly save more than I read and read less often than I would like. I found that when I was offline, so for instance when I was in New York City in the subways back in 2014, 2015, there’s no internet service and so there’s nothing else to do. I would read a ton on Instapaper. That is changing rapidly. I think even in airplanes now, most of the time you’ll have wifi. I’ve gone back to New York and almost every subway station you have LTE. I live here in the bay, I take BART, there’s basically service on the entire BART line, and I find that more and more there’s less time I’m offline, where I’m going to Instapaper, and so I do need dedicated time on the weekend or nights to actually go through and read them. There is times I’ll read a little bit during lunch, especially if it’s work-specific articles. The best productivity hack I have that’s Instapaper related is on the mobile application. If you press the ellipses button in the top right, you can press, there’s a sort option, and you can sort by shortest article. Then I’ll go and I’ll just blow through a ton of short articles and just do them really, really fast, and I’ll leave kind of the bigger, meatier ones for later. Another one that I do is I’ll go through periodically and I’ll just delete a bunch of stuff that I know I’ll never get to. Especially there’s tons of Donald Trump articles in there that are like, just no–

Craig Cannon [01:01:59] – Like, thought pieces about Trump you mean?

Brian Donohue [01:02:00] – Yeah, and there’s just no longer relevant, because so much has happened between today and two or three months when I saved it that it’s just no longer interesting or relevant. I’ll go through and I’ll delete a bunch of things like that. Or like this company raised this money, I’m like oh I don’t really need this actually. Those combination of things are the best productivity hacks I have around it, but making time to actually revisit the things that you save is very difficult. We’ve thought about building features to help with that, but it’s really hard to build that type of feature and not make it massively annoying for the person using it and make them feel bad about not going back to it.

Craig Cannon [01:02:42] – It’s the same thing as exercise.

Brian Donohue [01:02:43] – Exactly.

Craig Cannon [01:02:44] – Like until you really want to do it, it doesn’t happen, it’s just guilt.

Brian Donohue [01:02:46] – Exactly.

Craig Cannon [01:02:47] – Yeah, but do you ever see, I don’t want to mess with it, I think his name’s Dan Williams in London, he made a Chrome extension that was like send to Kindle but it didn’t do anything. It was like JavaScript void, and it was like, you could just click it.

Brian Donohue [01:02:59] – That’s awesome.

Craig Cannon [01:03:00] – It would trigger that thing and I actually did install it for a while, because I realized going back to my Instapaper, Pocket or whatever I was using at the time, I could pretty easily ascertain the stories that I’m actually going to read, and having more discipline around that was what allowed me to get, I mean I’m never at inbox zero on any of this stuff, but closer to it.

Brian Donohue [01:03:22] – Right.

Craig Cannon [01:03:24] – Also grayscale, have you experimented with that on your phone?

Brian Donohue [01:03:26] – I haven’t. I know it’s like a big thing people are doing.

Craig Cannon [01:03:29] – Grayscale plus airplane mode, you get shit done. Because your phone’s just so lame after that you can actually read. The last thing I wanted to talk about is all your hiking ambitions. What’s your training strategy lately?

Brian Donohue [01:03:44] – Sure. It’s interesting. I’m from the East Coast, I was not into nature. I think if you live in New York there’s, you kind of get sucked into the city and the vibe in the Bay Area is very different. The thing that I’ve really loved about living here is the easy access to nature. I started just by exploring and hiking. I did a lot of my first hikes here, my first 10 mile hike, things like that. I think as I started pushing the upper limits on hiking and doing things like going to Yosemite and doing Half Dome and doing these 16 mile hikes, I got into more camping, backpacking, doing much longer hiking. And so I think this year I’ve done like 10 backpacking trips all over the place, which has been pretty awesome.

Craig Cannon [01:04:33] – Well you did some big ones here, not just doing casual stuff, right? Like you did Whitney, you did Shasta, right? Have you done any other big ones this year?

Brian Donohue [01:04:40] – Yeah, so I think those were the two big ones. From backpacking it’s kind of been like well some of these mountains look really awesome, right? And so mountain climbing is a super dangerous thing, and so when I did Shasta, at least where it was heavily snow and ice, I went with a company that brings people up there. Yeah, I’m not trying to like, die on a mountain.

Craig Cannon [01:05:02] – Right yeah, it’s dangerous if you don’t know what you’re doing.

Brian Donohue [01:05:04] – Exactly. I did Mount Shasta, which was great. I did Mount Whitney this year, which was extremely hard. Mount Whitney is the highest peak in the lower 48. It’s in California here, it’s in the eastern Sierras near the Nevada border. I did that one basically in a day. I went up and came back, it was 13 hours, 8,000 feet of elevation gain. I had a massive headache at the top, which sucked. If I do it again, I’m definitely going to sleep overnight.

Craig Cannon [01:05:34] – Because you went from Lone Pine, right? You went from the East Side.

Brian Donohue [01:05:37] – Yeah, you start, I slept in the parking lot, like right outside the parking lot, and I think that it’s like 6,700 feet or 7,000 feet. Then you go up to 14,500. It’s a pretty big lift for one day. There was a campsite at 10,000 feet, I just didn’t get a permit for it, otherwise I’m not a masochist, I would’ve done it. And so I have been doing these pretty intense workout routines for mountain climbing specifically, and I started with just the Shasta one, it was like a 12 week mountain climbing routine heavily focused on endurance. A lot of cardio, a lot of long cardio sessions. Yesterday I did an hour on the stair master with 20 pounds in my backpack and just kind of doing things like that. What I’ve realized is like, you do hit these walls, but the more you can kind of like… feel like you want to give up. And the more you can break through them and get used to hitting the wall, breaking through it, breaking through it and doing that in the gym versus on the mountain is kind of a good strategy. And so I have some more ambitions, I don’t think I’m ever going to want to do Everest or anything like this, like that’s a little–

Craig Cannon [01:06:52] – Like real climbing.

Brian Donohue [01:06:53] – A little too extreme.

Craig Cannon [01:06:53] – Like ice climbing.

Brian Donohue [01:06:54] – I would be interested in that, I just, I’d want to balance having a good time outside with being safe, you know.

Craig Cannon [01:07:00] – Oh yeah, but there’s the whole categories of like, type two fun and yeah, I agree with you. I fall into the camp of enjoying the suffering, not the dangerous part.

Brian Donohue [01:07:10] – Yes, exactly. And I think with Everest if you need to put oxygen on in order to get up, it’s like you know. Maybe it’s just, you know, I know people that do it, but it just seems, and I know people do it without oxygen, and those people are awesome, but it just seems to me like maybe a step beyond what my ambitions are there. But I would like to do Mount Rainier, there’s a couple in South America that I’m kind of interested in doing, at least like go near. And it’s kind of been like a whole new thing for me, this whole area, and so it’s something I’ve really enjoyed living out here in California and exploring.

Craig Cannon [01:07:46] – Cool man. Well if someone wants to get in touch with you or reach out to you on the internet, what should they do?

Brian Donohue [01:07:50] – Sure, Twitter’s probably the best place. My Twitter handle’s @bthdonohue. I usually give out my email, too, but–

Craig Cannon [01:07:59] – It’s a lot of people, don’t worry about it.

Brian Donohue [01:08:01] – If you reach out to me on Twitter, I will give you my email address and we can chat, but I think that’s probably, we’ll start with Twitter.

Craig Cannon [01:08:09] – Cool man, alright. Thanks for making time.

Brian Donohue [01:08:11] – Yep, thank you.

Craig Cannon [01:08:12] – Alright, thanks for listening. As always, you can find the transcript and video at If you have a second, it would be awesome to give us a rating and review wherever you find your podcasts. See you next time.


  • Y Combinator

    Y Combinator created a new model for funding early stage startups. Twice a year we invest a small amount of money ($150k) in a large number of startups (recently 200). The startups move to Silicon