In this episode of Startups For The Rest Of Us, Rob interviews Nathan Chan of Foundr Magazine about his journey to success and what he has learned along the way.
Items mentioned in this episode:
Rob [00:00]: In this episode of “Startups for the Rest of Us,” I interview Nathan Chan of “Foundr” magazine. “Foundr” magazine is an online magazine, and Nathan bootstrapped this completely on his own two years ago, starting in about 2013. He was sued by one of the biggest magazine publishers in the U.S. within the first four months of starting. He’s gotten interviews with folks like Richard Branson, Ariana Huffington, Tony Robbins and Seth Godin; and he’s really stair-stepped his way up from not knowing what he was doing or how to do it into building a really solid brand and a profitable online magazine. This is “Startups for the Rest of Us,” episode 261.
Rob [00:47]: “Welcome to Startups for the Rest of Us,” the podcast that helps developers, designers and entrepreneurs be awesome at launching software products, whether you’ve built you first product or you’re just thinking about it. I’m Rob, and today with Nathan Chan, we’re here to share our experiences to help you avoid the same mistakes we’ve made. So, today I’d like to welcome Nathan Chan of “Foundr” magazine. “Foundr” is a tablet-based magazine, so on your iPad, or your android; or, I’m assuming you probably get it on – can you get it on Kindle Fire as well?
Nathan [01:14]: No, you can’t.
Rob [01:15]: Okay.
Nathan [01:16]: You can’t, but you can get it on mobile, too.
Rob [01:18]: On mobile. Okay. You can download the Founder app. It’s spelled F-O-U-N-D-R, and Nathan has somehow been able to secure interviews with some pretty amazing people: Steve Blank, Richard Branson –
Nathan [01:31]: Ariana Huffington, Tony Robbins, Seth Godin –
Rob [01:34]: – very nice.
Nathan [01:35]: – various – many more.
Rob [01:36]: He’s a bootstrap startup founder, and that’s why I wanted to have him on the show, just to talk about his experiences. The magazine’s been out since 2013. He’s learned a ton on his journey, and so although listening to this podcast, you may be thinking, “Well, I’m not going to start a magazine,” there’re so many lessons that Nathan has experienced and learned through his time that we’re going to dive into over the next 30 minutes.
Thank you so much for joining me today, Nathan.
Nathan [02:00]: Thank you so much for having me, Rob. It’s an absolute pleasure. I’m a massive fan of the show.
Rob [02:04]: Very cool. Talk to us a little bit about “Foundr” magazine: why’d you start it, and maybe give us maybe a little background about what it is and what the goal is.
Nathan [02:12]: Yeah, sure thing. I started, actually, Foundr while I was working my full-time job. I bootstrapped it, as you mentioned, from the ground up. I actually didn’t even leave my day job until I fully replaced my income, and that’s something that a lot of people don’t do. They usually go cold and just leave their job and just make it work; but for me, I’m a very risk-averse person. It all started because – also, you mentioned that “Foundr” is my first business. I’ve never ran a business before, and it all started from just the curiosity of always wanting to become an entrepreneur and not really knowing where to start, what it takes; and also the fact that I identified that there wasn’t really a publication out there – an entrepreneurial, business publication – that myself, as an aspiring entrepreneur, could relate to. I think magazines like “Forbes,” “Entrepreneur,” “Fast Company” – these are great magazines, and they produce great content, but I found it difficult to relate to. I think they go on the assumption that you’ve already started a business; or, you already have a business; or, you’re an experienced, accomplished entrepreneur, and I found it quite intimidating. I knew that podcasts were really not, and I also realized that there wasn’t really a magazine targeting the younger demographic as well – nothing that was known. So, I just thought to myself, “Well, let’s just give this magazine thing a try.” We launched just on the iPad while I was in my day job, and I said, “I’ll give it a good, hard crack for a year.” Then I built it up, left my job; and, yeah, here we are today. But I guess the magazine just stemmed from just my own curiosity and wanting, I think, to fill that void in the marketplace that I identified.
Rob [04:04]: Very cool. To give folks an idea of where you were at, you were basically working a full-time job. You bootstrapped this. You didn’t raise funding. Everyone who helped you work on the magazine is a contractor, you mentioned, so you have, I’m assuming, contract writers, contract photographers, contract designers and layout folks. I mean this really was the effort of one person and very doable. This type of thing is very doable by anyone – right – if you were able to pull it off?
Nathan [04:32]: Yeah, I think so, definitely. I’ll be very clear. We have a lot of people that are helping me behind the scenes, and we do have some full-time staff now; but, yeah, yeah. To pull it off it was just me, man, and just utilizing freelancers, contractors all around the world; and I think that’s the awesome thing about the Internet now.
Rob [04:50]: Yeah, for sure. This is really cool. You’re 31 episodes in. You started, it looks like, March of 2013. How did you get that initial kick-start? You probably spent months planning, designing, building that first issue; and you launch into the iOS App Store, I assume, the Android App Store at the time. What did you do? How did you try to find people and convince them to download the app?
Nathan [05:15]: Yeah. I remember the first day we launched, we had 70 downloads. I made $5, and that was the first $5 I’d ever made online [laughs].
Rob [05:24]: Wow. Very cool.
Nathan [05:27]: What I realized was I needed – I didn’t have any money, and we were bootstrapping, so I had to work out, “What is the lowest-hanging fruit?” I quickly worked out that one of the best ways for us to get more downloads – I kind of tracked it back. So, “What does it look like for someone to subscribe to the magazine?” Before that, they have to download the app. Then before that, how do they even find the app? I did all sorts of things – not too heavily, to be honest with you, Rob. I didn’t really do any social while I was in my day job, so it took me about a year to build up the magazine. For that whole year, all I focused on was shipping a monthly magazine every month and try and get as many readers as I could. I didn’t really touch social, didn’t really touch content marketing, couldn’t afford any paid customer acquisition; so, I really had to just took at my playing field and find, “What’s the lowest-hanging fruit?” “Where’s the starving crowd?” I identified if you have an app, one of the lowest-hanging fruits is App Store optimization. So, Google for the App Store, like SEO for the App Store. What I found was that there’s all these people looking for business-type magazines, and they’re searching for key search terms like “entrepreneur magazine,” “business magazine,” “startup magazine,” “startup.” So, what I got really, really good with was optimizing that whole funnel from finding the app to getting people to subscribe. I can tell you for a fact that anyone that first opens the magazine, we have a 30 percent uptake of people subscribing. Then from there, I can tell you, working backwards, that if you search for “entrepreneur magazine,” “fast company,” “Forbes,” we actually piggyback off all of those magazines. So, if you ever search for those magazines that you want to read digitally in the App Store or Google Play Store – not hardly ever our downloads come from the Google Play Store – I’ll be very clear – but in the App Store, if you search for that, any of those key terms, “Foundr” will come up. We play also on the fact that you get your free Richard Branson issue. We try and build that trust; make it a no-brainer; and, yeah, just take it from there. But App Store optimization has been massive for us, Rob.
Rob [07:47]: I like that, because I have this theory called the “stair-step approach” to bootstrapping, and typically it involves launching a small product with a single marketing channel that you get really good at, then expanding into others and moving up this ladder. Typically, it’s with different products; but it sounds like with Foundr, you launched it, and you got really good at App Store SEO and, for lack of a better term, and then you branched out from there. I’m assuming by this time, you’re doing social. You’re obviously doing podcasts to promote it and other avenues, but when you started out, just getting that single tool on your tool belt can be so valuable for a first-time entrepreneur.
Nathan [08:22]: Yeah, I agree. That’s pretty spot-on, Rob; because it was only actually when I left my job we went down the content path. We used to have a really crappy website. It was terrible. It was just a basic landing page to keep Apple happy; but, yeah, once I left my job, it actually freed me up to focus on the content marketing page, roll out the podcast and roll out social. Yeah, we’re kicking some goals with social now, like the stuff we do with Instagram. We’ve got an email database of 100,000 that we built in a year from 3,000. A lot of that traction’s come from Instagram. We’ve found a few other channels now as well.
Rob [08:56]: That’s pretty impressive. You said you built it on Instagram. Obviously, Instagram is heavily image-based, so was that pieces taken out of the magazine, like different pages or different stories that you’re putting up there?
Nathan [09:06]: Yeah. What I’ve found with Instagram is – same with all those social channels. If you go and look at “Entrepreneur” magazine, “Fast Company,” “Forbes,” a lot of them post quotes on Twitter, or Facebook. We do the same in Instagram. We post, like, 95 percent quote; and we post a little bit about the podcast, a little bit about the magazine, a little bit – it’s a very small portion – behind-the-scenes stuff. But the quotes work really, really well because they have that virality where people tag their friends. They share it. They screen-shot it. They repost it; and that’s worked very, very well for us.
Rob [09:39]: Yeah. See, I like this because anyone can take lessons away from this. Again, if you’re listening this, you’re not starting a magazine, per se, you hear what Nathan’s done as a first-time entrepreneur: a) he shipped. He just said, “I’m going to ship for a year, and I’m going to get 12 issues out, and I’m going to figure it out along the way. Then he focused on a single tool in his tool belt – it was this App Store optimization – and then expanded out from there. You’re now talking virality, which is how you went from 3,000 to 100,000 email addresses; and although Instagram may not be the particular channel if you’re running a B-to-B app, or if you’re doing other things there’s always byproducts. You’re basically taking byproducts of something you’ve already produced, which are quotes out of the magazine, which is your finished product that you’re selling. You’re taking these byproducts and figuring out where they’re going to catch. In your case, it is Instagram; but I can imagine for other apps there’re going to be other approaches. This is good stuff.
Nathan [10:29]: Yeah, I think it’s all about just, yeah, shipping every – producing something consistently every, single week; every, single day; every, single month and just focusing on it and just having a relentless ability to attack whatever it is you’re focusing on if you get a little bit of traction and just scaling that up.
Rob [10:48]: Speaking of scale, at this point, how many monthly readers to you have at this point?
Nathan [10:51]: We have 25,000 monthly readers.
Rob [10:53]: Got it. Looks like you have multiple channels now. You have the magazine, which is obviously your flagship. You’ve started a podcast. Are you interviewing folks that are also appearing in the magazine?
Nathan [11:05]: Yes. What we do with the magazine – and I didn’t realize this until later, but one thing we do is we do these interviews on Skype, just like me and you are doing, for the feature interviews in the magazine. Now, we’re actually repurposing – because we actually imbed those interviews within the magazine. What I realized after a year was I’ve got all these amazing interviews with all these super successful founders and hard-to-reach founders. Why not just get our best ones and put it out into the world with the podcasts? I know it’s a great tool, a great platform. I always said I didn’t want to do a podcast, and that was how we were going to differentiate ourself, and the podcast has really taken off. It’s been an amazing trust builder, so now it’s just like another, I guess, latch on our tool belt to build our platform, to build our reach and to spread the mission and the word of just really promoting entrepreneurship and showing people what it takes.
Rob [12:00]: Very cool. I’m curious. Do you do much of the writing in the magazine yourself? Or, is it all hired writers?
Nathan [12:05]: Yeah, no. We have a part-time editor who now helps with all of our content that goes out, because we’re pumping out a lot of content now, man. So, yeah, Tate, he’s from Boston. He manages all that, and then we have tons of contractor writers – you know, 15, 20 contract writers. I only write the “Editor’s Letter” –
Rob [12:24]: Got it.
Nathan [12:25]: – but in the early days when I first started and it was costing, like … oh, my God, man. It’s funny, thinking back. Operating costs to produce the first few issues was under $500 –
Rob [12:37]: Wow.
Nathan [12:38]: – and, yeah, I had to do some of the writing. I was getting my mom to help me do some stuff.
Rob [12:42]: Sure.
Nathan [12:42]: I was getting friends to help me do some stuff; but, yeah. No, long away from the writing and touching that now.
Rob [12:47]: Yeah, you were scrappy and lean at one point, and now you have to be –
Nathan [12:51]: [Laughs]
Rob [12:52]: – no, you have to be sane. You can’t work 80-hour weeks anymore. So, very cool. And then you’ve also branched out. I think folks will find this interesting. You’ve also branched in now to creating a couple of knowledge products, or information products. One is about marketing on Instagram.
Nathan [13:06]: Yeah, we have a crowd funding guide, but that’s just like an eBook that is very well-curated.
Rob [13:11]: Right, so you’re taking a little bit of a push into that area, right? What made you decide to start selling info products as well?
Nathan [13:18]: Yeah. What I realized was – the magazine was doing well, you know, a profitable, six-figure business – just the magazine alone. What I realized was a lot of people started asking me – because we were using Instagram as an amazing channel to grow the magazine and to build our awareness and reach and email database. What was interesting was I wrote this blog post and, still, to this day, it’s one of the most successful blog posts on our site. It was titled “How to Get 10,000 Followers in Two Weeks on Instagram,” and that just crushed it, man. Neil Patel always references it, all sorts of things. All these people would come up to me, and they found that blog post. What happened very quickly was a lot of people started asking me how I was doing this stuff, and then a lot of people started asking me to do consulting. I was like, “I don’t really have time.” “I don’t really want to focus on that.” I thought, “Why don’t I just create a course?” So, I just put out to our email list an email saying, “Guys, would this be something you’re interested in?” Even though our database was around 5,000, 7,000 at the time – this was very early, because we got some really great traction early on with Instagram within the first couple weeks. People were just like, “Yeah, I’d love” – hundreds and hundreds of responses from people writing back to me in our community. So, this was something our community as asking for. I launched a beta, and then we relaunched the full course, and then it’s been really, really lucrative for the business and also just the community that have signed up to the course, it’s amazing some of the results our students are getting. It was something that I was just like, “Wow! Okay, so this is something that our community wants. It’s something our community is asking for. They’re asking for more help,” and I’m constantly getting asked about all these other things around starting a business, how to scale – all these other things. So, what I’ve realized is “Foundr” is the front end of the business, and then we can further monetize and build it up for the back end. I’ll be very clear, Rob. I won’t be doing the teaching. I’ll have many other experts coming in, and we’ll be doing curated courses using the publishing model, where I offer somebody an opportunity to either white-light all their content, or their video course that they have existingly. Then we package it up in the Foundr way with our tools, with our platform, with our systems. Then we do a deal, like an ongoing profit split. That’s the model we’re going to scale up. So, “Foundr,” podcast, blog content, social content, all on the front end. Right now, 95 percent of our content is free; and then if people want more help, it is there. I speak to a lot of people in our community. I actually jump on the phone whenever I can and just find out what their biggest problems, frustrations, desires are. A lot of things I’m hearing is people are saying, “Nathan, we love the stuff you’re producing. We love the free stuff, everything you’re doing; but sometimes we just need more help,” “Need more help.” Like, “I want to try this.” “I want to do this.” “I want to do this.” People always love that handheld content if they don’t have time to stuff around, or – you know, a lot of people just want their hand held. So, I think this industry, the online education industry is a multi-billion-dollar industry; and I think we’re now better equipped, then, to tap into that.
Rob [16:44]: What I like about the approach that you’ve taken is the common approach for building an audience these days is to start a blog or a podcast; and then you build the audience up, you find out what they need, and then you build products for them. You’ve taken a different approach and started a magazine, then made that profitable and then are looking at basically these content upsells. I’ve seen a few others. I know “Entrepreneur” magazine has their book line, and they have some events that they throw. I guess a lot of magazines wind up throwing events in order to do it, but I do like this hybrid model; because – let’s be honest – just purely publishing a magazine or a newspaper these days, even online, is not a growth business, per se. People expect the content to be free. I know they do pay for yours; but it’s going to be very, very difficult to build that into, let’s say, a $10 million business, or a $20 million-dollar – I mean you just can’t get to the scale. Whereas, adding these upsells and actually charging money for really valuable information and being able to charge a premium for these courses that are put behind your brand name – because your brand name obviously has a lot of equity with the folks that are reading our magazine and respect what you’re doing. Then, if you can place that on front of some $19 eBooks at this point, and then maybe it’s a $100, $200 video course, maybe at some point you throw an event – that’s where you’re going to be able to really grow this business and increase your revenue.
Nathan [18:03]: Yeah, I agree. Look, don’t get me wrong, Rob. I’ve got my eyes on building an eight-figure business. I think we can do it, do be honest with you, probably in a couple of years. That’s my goal. Now, it’s all about just finding out further ways to serve our community; just keep producing epic content; and, yeah, just rolling out and serving as many of our people in our community as we can and just producing more epic content, whether that’s paid or free.
Rob [18:28]: Very cool. I’m interested to hear how – you started this magazine from scratch. You were, in essence, kind of an unknown, I’ll say; and within eight months, your eighth issue, you have Richard Branson on the cover. In fact, your sixth issue has Neil Patel. You got Ed Dale in issue two. You got some big names early on. How did you possibly pull that off?
Nathan [18:51]: Yeah. One thing I realized, Rob – I didn’t know this when I started, but having a magazine is very, very powerful for building authority; and people take you really seriously. Some of the people we’ve got lined up for 2016 for our covers is crazy, like really, really hard-to-reach founders. I don’t know if I can say, but we’re talking to billionaires and stuff like that to get on our front covers – more billionaires, not just Richard Branson. Yeah, people take you really seriously, Rob; and you have a little bit more weight as opposed to having a blog or a podcast. I didn’t realize this until – it took me a few months to work this out, because if you actually look at the front cover of the first issue, Rob, I didn’t even have a successful person on the front cover. I had a stock image [laughs], and that’s kind of funny, looking back; because now we don’t have any problem. The reason we had that stock image was because no one would get back to me, but I just kept pitching, man. I just kept hustling, and within the first four months, I realized, “Richard Branson’s been on the front cover of every, single business magazine. Why can’t he be on the front cover of ours?” I just went down this path of finding out how to contact him, and I made a lot of phone calls. One thing: if you want to get any ambassadors for your brand, well, here’s a few, quick hacks for people that I know all you guys that are listening are going to love. One, make phone calls. I found that they get so much better cut-through, if you want to find ambassadors for your brand, if they’re an influence in whatever niche you’re in. If they have a book, try and contact the publishers. Find out who publishes that book, like Random House. Find their PR team. Speak to them and then try and find either the company’s PR team, or the agency that represents that person or company’s brand – their PR team. Then just try and find those people, because they’re actually paid to find press, so they can make you look good whatever kind of mutually beneficial exchange in value you come up with. Then I found myself about four months into the magazine on the phone to Sir Richard Branson’s head of PR. I pitched her over the phone. I remember I was so nervous. I was stumbling, and she said, “Look, please understand we get, like, ten requests a day; but shoot me an email. I promise I will get back to you. It might be a while, but I will get back to you.” I pitched for a Skype interview, and she said, “Sir Richard’s really busy, but he can do an email interview.” Then from there, his team worked with me to get the photos, and we come up with a feature, and we ask the questions. We get the answers. Then we come to a story, an angle; and then from there, to be honest, Rob, that was Richard Branson. Then I’ve just used that as a springboard to gain influence in the space. Yeah, just keep pitching, man. I’m just very, very relentless and very organized now, too. We’ve got up until June 2016 covers booked with some very cool, hard-to-reach founders. They’re going to be amazing interviews, hard. It’s going to be really solid content. Yeah, I’ve just played on that springboard. Another good tool that I use in my arsenal, if you are pitching over email, is a Gmail plugin called “Rebump.” Because you come from an email marketing background, you might know of it. It’s amazing. It allows you pretty much to just “set and forget.” When you are pitching business development style, you send an email. You get the Gmail plugin installed on your Gmail, and then you tick that little box. Then there’ll be literally, like, templated emails that will follow up; and it knows, because it’s connected to your Gmail, if somebody writes back and just flat-out follows up for you. That works very, very well.
Rob [22:39]: Yeah, I use Boomerang for that –
Nathan [22:41]: Yeah.
Rob [22:42]: – but it doesn’t automatically follow up. It just boomerangs it back in, and then I have to do another reply; but that’s what I commonly use. I think that’s a really good tip. That ties back in with something Steli Efti was saying. He’s kind of the master of startup sales, and he was saying that at MicroConf last April – basically, that you just have to follow up. Oftentimes, he wouldn’t get a sale, or wouldn’t get an answer until he followed up 15, 20, 30 times; but the people who are doing that are the ones that probably are the ones that are getting Richard Branson and Daymond John and Seth Godin and Tony Robbins like you are. I’d imagine these days, though, with all the issues you have and with all the people you can mention that you’ve already interviewed, you just have such credibility that I bet – when you emailed Seth Godin, was it even that big of a deal? Or, did he say, “Sure, I’ll just come into the magazine”?
Nathan [23:27]: Yeah, you got it spot-on, Rob. I just had to build it up, just build up that credibility and just keep – I used Richard Branson as a springboard. Yeah, with Seth Godin, it was pretty much I emailed him; and then he emailed me back in the morning, saying, “Can you do it in two hours?” I was like, “Yeah, [?].”
Rob [23:43]: That’s great.
Nathan [23:43]: So, we had the podcast interview; and, yeah, it was really cool; really, really fun. Great guy.
Rob [23:48]: Yep, that’s what I’ve heard.
I want to wrap us up on this final topic. You told me offline that you were sued by one of the biggest magazines in the first four months of your starting. Obviously, you lived to tell about it. Talk to us a little bit about what happened there and how you recovered. I’m definitely interested to hear how you felt during that time.
Nathan [24:09]: What happened was – it’s funny, looking back. We were just talking about this offline. It is not a very nice feeling to be sued, especially when it’s your first-ever business, and especially when you have no money and you don’t never, ever in the world ever expect that to happen. Just always play it really smart. Don’t ever think it won’t happen to you, because it might. You just never know. What happened to me was the magazine actually wasn’t called “Foundr.” We had to change it four months in. I remember we’d just locked down the interview with Richard Branson, and I was just thinking, “Wow. We’re kicking some [grows?].” Then I woke up in the morning about 7 a.m., about to go to my day job, and I checked my email. I got this email from this lawyer saying, “Hey, Nathan. I’m from so-and-so. I just want to know if you weren’t aware. You’re being sued by this company. They’re one of the biggest print magazines in the States.” He said, “Yeah, I just wanted to let you know you’re being state in Dallas, State [of] Texas. You’re being sued by this company.” He’s like, “You probably want to move fast.” He’s like, “I actually have a really good relationship with the judge on this case, so you should totally get me to represent you.” [Laughs] And I was just like – 7 a.m. in the morning, I was freaking out. I was like, “Is this sophisticated spam?” I haven’t been served. I didn’t know what the hell was going on, man. You know, it was crazy! A long story short, I had to change the name. I’m so glad that it happened now when it did, because we got a ten times better name, ten times better branding. It was such a blessing in disguise; but at the time, Rob, I was so stressed out. It was really, really crazy. I was lucky enough I didn’t even have to pay any money just because I had some amazing mentors that helped me through that whole process. Some of my mentors had been sued before. We just changed the name, and they left us alone. It was, yeah, really a blessing in disguise, [a] great lesson to be learned early on. But for the audience, when it comes to trademark infringement, if you’re erring on the side of caution, just don’t even do it. Make sure that your name, your branding is very individual and unique. If you think to yourself that it might be a little bit similar, or it might be a concern, just, yeah, go down the path of making sure you protect yourself. I think that’s really important.
Rob [26:34]: Right. Then the other lesson – because I’ve heard from several folks who’ve had run-ins like this – is that when you’re contacted – in an ideal world, they wouldn’t have just sued you. They would have sent you a letter letting you know about the issue, and then – you know what I’m saying – and then send a [?] – I’ve had a friend who’s had a couple different WordPress plugins, and as it turns out, it accidentally infringed on trademarks of company names, because they were helping people use that company through WordPress. So, it’s a natural thing to include the name in there. But they’ve been nice enough not to just sue him. They sent him a letter. Typically, it’s an email. It says, “Hey, I’m in the so-and-so department. This has come to our attention. We want to work with you to help you transition,” you know? They don’t give some hardline. There’s two ways to go about this, right? You can come in swinging and be like, “My lawyer will be in touch!” Or, you can say, “Let’s work with you on this.” That’s the way that I think so many of these cases turn out, and I think it’s such a better approach to just be able to resolve it without going to court; because let’s be honest. If you actually go to court, the only people that win there are the lawyers. They get paid a lot of money, and even if you win in –
Nathan [27:39]: [Laughs] That’s right.
Rob [27:39]: – court, you almost never really win in court. There’s just not that much money that comes out of it for either side.
Nathan [27:45]: Yeah, that’s exactly right. And, look, dude, I had no money at all. So, [laughs] you know.
Rob [27:49]: Wasn’t gonna happen, yeah.
Nathan [27:50]: [Laughs] Yeah, that’s right. We weren’t really making much money at all, anyways.
Rob [27:55]: Yeah. Well, very cool. Thanks again for coming on the show. If folks want to keep up with you online, where should they look?
Nathan [28:01]: You’re welcome, Rob. Best place is just hit up our website: foundrmag.com, F-O-U-N-D-Rmag.com. Now you know why we spell it “Foundr” without the “e,” because there was no one in the world that had that name, so we can be protected.
Rob [28:19]: Very cool. Thanks again.
Nathan [28:21]: You’re welcome. Absolute pleasure.
Rob [28:23]: If you have a question for us, call our voicemail at 888.801.9690, or email us at: firstname.lastname@example.org. Our theme music is an excerpt from “We’re Outta Control” by MoOt, used under Creative Commons. Subscribe to us on iTunes by searching for “startups” and visit startupsfortherestofus.com for a full transcript of each episode. Thanks for listening, and we’ll see you next tim
In this episode of Startups For The Rest Of Us, Sherry Walling and Ali Taber discuss what it’s like being married to a founder and share their experiences on how they balance work and family life.
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Sherry [00:00:22]: In this episode of “Startups for the Rest of Us,” Ali Taber and I discuss what it’s like to be married to a founder. This is “Startups for the Rest of Us,” episode 230, the five-year anniversary edition.
Welcome to “Startups for the Rest of Us,” the podcast that helps developers, designers and entrepreneurs be awesome at launching software products whether you’ve built your first product or you’re just thinking about it. I’m Sherry.
Ali [00:00:34]: And I’m Ali.
Sherry [00:00:35]: And we’re here to share our experiences to help you avoid the same mistakes we and our husbands have made. So, what’s the word this week, Ali?
Ali [00:00:44]: Well, my name is Ali Taber, and I’m married to Mr. Mike Taber, and I am currently a group exercise fitness instructor, a personal trainer, and a small fitness studio owner. And we have two boys, six and-a-half and eight, and Mike and I just celebrated our tenth wedding anniversary in October.
Sherry [00:01:08]: Woo-hoo. Congratulations.
Ali [00:01:09]: Yeah. Yeah, we made it ten years. Whoo. A decade.
Sherry [00:01:11]: Double digits.
Ali [00:01:13]: Yeah.
Sherry [00:01:15]: And I am Sherry Walling. I am married to Mr. Rob Walling. I’m a clinical psychologist, and I have a private practice and teach. I’m at a couple of different graduate-level programs. I’m the mother of two sons as well, and Rob and I are coming up on our fifteenth anniversary in about a month.
Ali [00:01:38]: Wow.
Sherry [00:01:39]: I think –
Ali [00:01:39]: Congratulations.
Sherry [00:01:40]: – hopefully, he listens to this, and it reminds him to begin shopping now.
Ali [00:02:01]: MicroConf Europe has been in October the last two years, and he was looking at dates or whatever, and he’s like, “How about this weekend,” and I’m like, “You know that’s our anniversary weekend, right?” And he’s got that look like, “Oh, right. Right. Ten years. Okay. So, looking for different dates now.”
Sherry [00:02:06]: I’m surprised he just didn’t roll over and say, “But I’m giving you a trip to Europe”
Ali [00:02:12]: Yeah. I’ve never been to a MicroConf, and that is something I hope to remedy soon, but we shall see.
Sherry [00:02:20]: Yeah. What’s the story with that? I wasn’t quite sure I really believed that Mike was married.
Ali [00:02:26]: It just doesn’t seem to work out with our schedules and with the kids’ schedules, and we don’t really have family nearby. His parents are in Upstate New York, and my mom’s not that far way, but she works full-time, still. It’s either been a scheduling conflict or a “I really can’t afford to fly the whole family to Europe for a week,” or whatever, “or two weeks,” or what have you. And there’s always a huge time difference. I mean even the Vegas, it’s a three-hour time –
Sherry [00:03:00]: Yeah, it’s a –
Ali [00:03:00]: – difference for us.
Sherry [00:03:01]: – pretty big disruption with your family.
Ali [00:03:03]: Yeah, and it’s a ten-hour travel. Between the connecting flights and the time difference, it just never really has seemed to work out.
Sherry [00:03:11]: Well, maybe someday.
Ali [00:03:30]: Someday. I’m hoping someday. He really wants me to come. He was really disappointed a few years ago, and he was like, “I want you to come.” And I’m like, “What am I supposed to do with the kids?” It’s just like leave them with a cell phone and say, “Call us if you need anything. We’ll be back in three days.” It doesn’t really work that way when they’re four and five. They’re older now, so it’s a little bit easier. But someday.
Sherry [00:03:33]: I bet they’d have a lot of fun in Vegas.
Ali [00:04:01]: We were trying to do it this year. We talked about bringing both of the kids out to Vegas and making it a family vacation, trying to do it the week of spring break so I wouldn’t have to get the phone call from the principal like, “Hey, you know you’re not supposed to take your kids out for vacation other than school vacation weeks.” But so much goes into booking the hotel and which hotel they can get and which week they can get, and nothing seemed to match up in our favor. So, that was kind of a bummer. Whatever.
Sherry [00:04:009]: Yeah, there should be some perks. Since you’re the wife, you should be able to schedule MicroConf around your schedule, but it doesn’t really work that way. Does it?
Ali [00:04:11]: Yeah, it doesn’t really work that way.
Sherry [00:04:12]: We’re not that powerful.
Ali [00:04:19]: No. No. I’m like, “Just schedule it this week.” He’s like, “It doesn’t work that way.” Why not? It should.
Sherry [00:04:19]: Make it work.
Ali [00:04:25]: Make it work. Tell those Vegas hotel people they need to make this work because you have an angry wife.
Sherry [00:04:50]: That’s sort of a nice commentary on what it’s like to be married to a founder, though. In a sense, you’re married to somebody who has a lot of autonomy and flexibility in their life, but it doesn’t always translate to being that simple and easy once you add in the other dynamics of family and other commitments that you have.
What have you enjoyed about being married to a founder, or, to Mike, specifically?
Ali [00:05:42]: Well, I never probably would’ve started my own fitness studio if Mike wasn’t involved in being a founder and being an entrepreneur and starting his own business and coming up with product ideas. He really kind of gave me that confidence to do it, not to be afraid of failure, because I never wanted to be a business owner. I never thought I was going to be a business owner. It wasn’t something like, “Yeah, I want to own my own business someday.” I was like, “No. I don’t want to own my own business.” Both sides of my family had had family businesses, and I’m just like, “Ugh. I’ve seen what that looks like, and I don’t want anything to do with it. I want to show up to work. I want to do my job. I want to get my paycheck, and I want to go home and leave office at the office.” And that was fine when I was a graphic designer. That’s what I did before motherhood. I was a graphic designer, and I had a career before graphic design, too. I’m on my third career.
Sherry [00:05:44]: You’re more advanced than the rest of us.
Ali [00:05:53]: Well, I don’t know about that. Some people would call it being fickle. I don’t know. Life keeps changing, so I keep trying to change with life, I guess, and my interests.
Sherry [00:05:58]: Well, you’re sort of a serial founder, too, in that way. You’re founding different careers.
Ali [00:06:04]: I guess. Yeah, I guess that’s one way to look at it. My student loans don’t really look at it that way; but, you know. Whatever.
Sherry [00:06:21]: Well, I think you were talking about how the fact that Mike is a founder and has started a number of different things has made it more easy, or has allowed you to be more supported in your ability to start your own studio.
Ali [00:06:50]: Yeah, absolutely, because I know if I ever have any questions, and even though it’s so different than what he does in that it’s a brick-and-mortar, and I’m dealing directly with customers as opposed to developing a product that’s going to be sold to a business. So, the dynamic is a little bit different, but a lot of the same kind of marketing applies, and the time that you have to put into building a business is all relevant.
Sherry [00:07:02]: Yeah. I mean he sort of understands the process of making something and being the one who is holding all the pieces together. And so it’s helpful to have him as a partner in that, I would imagine.
Ali [00:07:06]: Yeah, it’s been really good to have him on my side. That’s for sure.
Sherry [00:08:04]: I think we’ve kind of experienced that in our family. And I think me, personally, like you, I’ve done some career shifting and started as a traditional, tenure-track professor and just really didn’t like it. I think it was because Rob had had a couple of really great jobs. High-paying, really fabulous jobs, that he left simply because he really just didn’t like them. I know that sounds sort of obvious, like, “Oh, you don’t like your job? Leave it.” But when you get a Ph.D. and do all of this work and plan to be a professor, it was a really big shift and really hard to make that decision. But because I had seen someone else do it, someone else walk away from something that on paper looks good, but in reality it wasn’t right for Rob, and in this case wasn’t right for me, it made it less scary to take that leap into a less traditional job structure. And I think we’ve –
Ali [00:08:05]: Yes.
Sherry [00:08:31]: – seen it with our kids, too. Once you step off that 9-to-5, someone-else-pays-your-paycheck path, all number of things become possible when you’re more flexible. And so we’ve done some different things educationally with our kids, and I think it’s really affected the way that we’ve structured our family, including taking them out of school for a month to go to Thailand last year.
Ali [00:08:34]: Right, yeah. Were you guys homeschooling then? I know you were doing that for a while.
Sherry [00:08:42]: We homeschooled for two years, and now, actually, my oldest son returned to traditional school. And my youngest son is going to kinder next year. He’s only four.
Ali [00:08:43]: Ah.
Sherry [00:09:13]: No, he was in school, and we just made an independent study arrangement. We kind of said, “We have these tickets, and we’re going. So, if you want him to be a student, we’ll have him do his homework.” We apologized. We didn’t ask permission. We just did it.
So, how do you two work out taking care of kids and both running very separate businesses? And Mike, he’s no longer consulting, but he was for a long time consulting and traveling a lot, right?
Ali [00:10:00]: Yes, he was. That was really tough. I didn’t really do much professionally when he was traveling a lot simply because I couldn’t with the type of business that I was in, where I had to be present for classes, or present for clients. It was really hard. He basically traveled, and I did the family stuff. I was basically a stay-at-home mom. I did all the cooking, all the cleaning, all the laundry, all the stuff that made it possible for him to just get on a plane Sunday night, be in a different city, fly home Friday night and then be home for a day and-a-half and then get on a plane. I mean there were months that it was back-to-back weeks of traveling, and he saw the kids a day and-a-half before he was back out on the road. It was really, really tough. So, I’m really –
Sherry [00:10:01]: Wow.
Ali [00:10:13]: – glad that he’s not traveling anymore. And it’s really allowed me to start to work more outside the home and develop a business for myself and for us as a family, too.
Sherry [00:10:20]: Yeah. Of the ten years that you-all have been married, how many years was he traveling like that, keeping that kind of schedule?
Ali [00:10:27]: He started traveling right after I got pregnant with Luke, and Luke’s just turned eight. So –
Sherry [00:10:28]: Wow.
Ali [00:10:42]: – I mean it wasn’t always back-to-back like that. And there were definitely some years where his travel was less than years. There was at least one year where he was gone 42 weeks of 52.
Sherry [00:10:43]: Whoa.
Ali [00:10:43]: Yeah, he was travelling. Yeah.
Sherry [00:10:56]: [For] him [to] make the transition from doing side businesses to making those his primary vocation sounds like it’s probably a game changer for your family.
Ali [00:10:58]: Moving away from the consulting and doing –
Sherry [00:11:03]: Yeah, where he’s making money and has products out at Shark and those kinds of things.
Ali [00:11:32]: – yeah, it’s really changed how our family dynamic is. He’s home. He sees the kids. We’re all more involved in each other’s lives now as opposed to being a weekend parent. It’s been a huge shift for him, too, because there’s so much more he’s involved with. He’s like, “Homework? What’s homework? I don’t know what these kids have to do for homework.” I’m like, “It’s this, this, this, this and this.” And he’s like, “How do you know all this stuff?” I’m like, “Well, I’ve been doing it forever.” So, that’s been a huge shift for him, having to be more involved as well.
Sherry [00:11:36]: It sounds like a lot of the dynamics have probably changed with that transition.
Ali [00:11:38]: Yeah, it has, but in a good way.
Sherry [00:11:42]: Yeah, and it’s allowed you to have the time and support to start your own business. Are you enjoying that?
Ali [00:12:17]: I am enjoying it. It’s been a little scary, but also really rewarding just to see progress in clients and having them tell you, “You’ve completely changed my life.” “You’ve saved my life.” I had a client who, he was on his way to a grave: high blood pressure, high cholesterol. He’s off all his meds. He’s perfectly healthy now. I was like, “See? Diet and exercise. Pretty amazing stuff.” So, just seeing that transformation for people, being able to work with them more one-on-one and being a part of that has been really amazing.
Sherry [00:12:20]: That’s great. It sounds like it’s really rewarding.
Ali [00:12:24]: It is really rewarding. It’s exhausting, too, because they can also be very needy.
Sherry [00:12:26]: Yes. Yes.
Ali [00:12:49]: “Should I eat this?” “Should I not eat this?” “What do I do with this?” “How do I do this?” But it’s good. It’s really good. And then just figuring out how to make the studio run, how to get the schedules. Do I need to bring in more instructors to help me with all of this? What can I outsource? What do I need to do myself? How do I market this? Mike’s been really helpful with giving me some ideas about how to really grow the business.
Sherry [00:13:12]: It sounds like there’s a lot of parallel process, though, in that scAling-up process that I know that Mike and Rob talk about a lot. Like, how do you decide when to hire contractors? How do you decide when you need more employees? And the pros and cons of that, and then, of course, marketing is a big conversation always. Sounds like you and Mike probably have a lot to talk about at night after the kids go to bed.
Ali [00:13:48]: Yes. Yes, we do bounce ideas off each other. He’ll help me with stuff. He’s been writing this book, too, and he needed to get the cover done. And he got it back, and I’m just like, “Do you want me to just get this done for you so you can be done,” and was able to just whip out my graphic design skills from my back pocket, from my previous life. And we stayed up one night after the kids went to bed and got that out the door. And I’m sure you and Rob go through this, too. You really have to work not just as a partnership in your marriage, but there’s a partnership with your businesses, too.
Sherry [00:13:50]: Sure, yeah.
Ali [00:13:52]: You’ve spoke at MicroConf, right?
Sherry [00:14:30]: Yeah. Yeah, and we’re doing a podcast together now called “Zen Founder,” where we talk about actually a lot of the things that you and I are talking about today, kind of work-life balance issues and mental health, managing anxiety, all of the kind of human side of doing a startup. And so that has actually been really fun for he and I to join forces and work together in a more formal way. Our fields, of course, are very different. Although we certainly have a lot of things in common. We both supervise people, manage people. So, no, there’s a lot that we talk about that’s sort of overlapping in our two work lives, but to be able to really do something together is really fun.
Ali [00:14:35] And so how do you guys balance the family and the professional life?
Sherry [00:14:44]: It’s like playing Tetris. It’s like figuring out where all of those little boxes can go and find a little spot.
Ali [00:14:46]: Like Google Calendar on crack, right?
Sherry [00:14:48]: Exactly what it is.
Ali [00:14:55]: Who’s in charge of this? Yeah, and everything’s color-coded, and “You’re picking up, and you’re dropping off.” “And here’s the bus.” And, “Who’s making dinner tonight?”
Sherry [00:14:57]: Right. No, it is –
Ali [00:14:58]: [Crosstalk].
Sherry [00:15:38]: – very much like that. Yes, and we have this Sunday night meeting. We work on our Tetris board. We just figure out who’s going where and what help we need and what babysitters need to come when and where. Some weeks, it’s kind of crazy, like we’re both going 18 different places in a day. But it’s another way, though, that’s fun to be partners because we’re both pretty invested in the well-being of our kids, and we’re invested in each other. And so we just figure out as best we can to make sure that everybody’s getting what they need at a given day. And sometimes that’s really challenging, but mostly we problem-solve together.
Ali [00:15:41]: I like your idea about the Sunday meetings. I’m going to write that down.
Sherry [00:15:41]: Yeah.
Ali [00:15:45]: “Have Sunday meeting.” “Need Sunday meeting.”
Sherry [00:15:47]: That’s when the Google Calendar magic happens.
Ali [00:16:09]: Yeah. Usually, I just slap stuff on there and share it with him. But he doesn’t always see it, and sometimes it doesn’t always sync up. I’m like, “I put it on the calendar.” And he’s like, “Well, it’s not on my calendar,” and then that’s a whole other, like, when technology fails you. And then you’re yelling at your spouse, because it was on the calendar but they didn’t see it because it didn’t sync right, or whatever. So, it’s good to have an actual face-to-face meeting –
Sherry [00:16:10]: Totally, especially in –
Ali [00:16:12]: – to work that stuff out.
Sherry [00:16:24] – highly technology dependent families. I think if Google Calendar somehow went away, I would just wander around in circles, really unsure of where I was supposed to be and what was going on.
Ali [00:16:27]: I’d cry. I’d just be like, “I don’t know what to do.”
Sherry [00:16:28]: “I’m lost.”
Ali [00:16:34]: “I don’t have my list of my appointments and what I’m supposed to do right now.” Oh, man.
Sherry [00:16:53]: I guess since this is the five-year anniversary episode of “Startups for the Rest of Us,” maybe we could do a little bit of reflecting back about what the last five years have looked like. One thing that Mike has talked about at MicroConf and in a couple of other places is that he’s had some pretty significant health issues over the past couple of years.
Ali [00:17:57]: Yeah, he has. He’s had back issues since I met him in 2001. That’s always been an ongoing issue with him. And then more recently was his low testosterone diagnosis, which was the most recent health issue, which actually was kind of trying for both of us because he just wasn’t himself, and he didn’t know what was going on with him. He didn’t feel right, but he didn’t know what was wrong. So, I think he really struggled. He was really unmotivated, and a lot of the symptoms of depression are similar to those for low testosterone. So, I think he tried to do a lot of things to get him out of this, quote, unquote, “funk,” and none of it was working, and it was really stressful on our marriage. And when he finally went to see the doctor, the first thing she did was treat him for depression, like, “All right. I’m going to put you on antidepressants.” You know, they give you that mental health questionnaire when you go see your general practitioner. I don’t need to tell you. You know what they are.
Sherry [00:18:09]: Yeah, yeah. “Do you ever feel listless? No motivation? Tired? Like you have no appetite, or to much appetite?” Yeah. So, there was some screening, and he just marked them all because that’s what he was experiencing, but it wasn’t depression.
Ali [00:18:27]: Right. So, big, red flags when you mark “yes” to everything on there. So, she put him on antidepressants, and he took them for a while. And then he was just like, “These aren’t helping. I’m not depressed.” Of course, he just took himself off of them, which that’s another thing. You can’t just take yourself off that stuff. You need to go see your doctor. People do that kind of stuff. That must drive you [crosstalk] –
Sherry [00:18:29]: I don’t prescribe medicine, no.
Ali [00:18:29]: – okay.
Sherry [00:18:40]: No. But I work in a pretty integrated clinic, so I work very closely with psychiatrists. So, I have those same conversations with people about like, “Oh, you can’t just stop your medicine. You have to” –
Ali [00:18:40]: Yeah.
Sherry [00:18:43]: – “talk to us first. You’ll get sick.”
Ali [00:18:47]: Right. Yeah, you can’t just stop taking it. You’re supposed to wean yourself down and this and that.
Sherry [00:18:47]: Yeah.
Ali [00:19:01]: But anyway, she’s like, “All right.” She had sent him for some more tests and discovered the low testosterone and put him on a testosterone treatment, which is a gel he’s got to rub on his body.
Sherry [00:19:03]: And he’s doing much better now, right?
Ali [00:19:09]: He’s doing so much better. And it was almost like a relief. It was like, “Ah. Thank God there’s a reason I’m feeling this way.”
Sherry [00:19:27]: Oh, sure. Once there’s a problem, then you can work on figuring out what to do about it. That’s fantastic that he’s doing better.
And so the last five years, with all of the travel and the illness, there’s been a lot that’s been going on while Mike has been working on this podcast.
Ali [00:19:40]: Yeah, I guess so. It all seems kind of a blur. I mean we said, like, “God. They’ve been doing this for five years.” I’m like “It feels like a blur.” I don’t even know. It’s just so much has happened in the last five years. I’m sure everybody feels that way.
Sherry [00:19:43]: Yeah, we’re just in a time of life when time moves really fast, I think.
Ali [00:19:50]: Yeah, and you turn around and you’re like, “How’d the kids get so big?” Another year’s gone by, and –
Sherry [00:20:25]: I think the last five years, we’ve moved across the country, had a child. I changed jobs. Rob has bought and sold a couple of apps and companies and things. Started Drip. Maybe he started HitTail. No, I think we had HitTail, or, he had HitTail before then. But, yeah. So, life looks phenomenally different now than it did five years ago, both for him and for us as a family. And I guess the podcast listeners have probably walked alongside that process with Mike and Rob as their lives have changed.
Ali [00:20:30]: – absolutely. So, how do you feel about Rob’s latest product, Drip?
Sherry [00:21:53]: I think it’s cool. So, Rob and I have a little bit of an interesting arrangement. Even though we’re very connected and we do a lot of things together, even professionally, I’m pretty separate from the day-to-day running of what’s going on with the apps. So, I know that he has said over and over that he will never do this again. He will never start an app from scratch and do all of the design and architecture. I kind of ignore those statements, because I feel like I’ve heard them before. But, generally, I think Drip is kind of his mistress a little bit.
I think that’s a little bit how it is. He’s got HitTail. He’s got Drip. He’s got a couple of other things going on, and I sometimes have to vie for some attention from them. Generally, it’s gone fairly smoothly. There was a time about six months ago when he was really worried about the revenue flow, because he’d just hired several people, but, Drip wasn’t quite having the momentum that he needed it to have for the number of folks that he had hired. And he was sweating it. And it was really filtering over into our family life and our relationship, and I was getting a little Drip-angry. Like, “Get this app out of my life. This is causing too much trouble.” But since then, I’ve had more love for Drip. Drip is pulling its weight a little bit more.
Ali [00:22:19]: Yeah. That is true, though, how the stress of the business can really change the dynamic of your marriage and your family. Like you said, “Ugh. I hate Drip.” or, “I hate that product, because it’s ruining my life right now.” But it’s one of those things that kind of goes with being married to an entrepreneur. It’s interesting to hear you talk about it like that, because I’m like, “Oh, all too familiar with all of what you just said.”
Sherry [00:22:28]: Yeah, like the emotional quality of your relationship rises and falls along with the AuditShark, or the Drip growth curve line.
Ali [00:22:28]: Yeah.
Sherry [00:22:34]: How are you feeling about AuditShark? Do you and AuditShark need any couples therapy?
Ali [00:23:06]: Oh, yeah. I mean Mike’s been working on AuditShark for a really long time. It’s a very complicated product, and I remember when he first told me about it, he had that little-kid gleam in his eye about how amazing it was and this and that and everything he wanted it to be able to do. And of course, I just glaze over because I’m still not tech-savvy. I’m so far from any of this stuff. So, he gets all excited and tells me stuff, and I just glaze over. My eyes just glaze over, and he’s like, “You’re not even listening to me, are you?” And I’m like, “I’m listening. I’m listening.”
Sherry [00:23:09]: “I’m trying. If I understood the words you were saying.”
Ali [00:23:34]: Yeah. I’m just like, “I don’t even know what you’re talking about.” I’ve learned more about HIPAA Laws and all this security software stuff. I’m like, “You’re speaking a different language right now, but I’m doing my best to keep up.” But he’s put a lot of blood, sweat and tears into it, so it’s hard to be “Down with AuditShark.” because I know how much nurturing of the product that he’s done.
Sherry [00:24:10]: And I think that is what’s really hard about being married to a founder. It’s not just that they have an intense or demanding job, it’s that so much of themselves is wrapped up in it. And so, really, if AuditShark, or if Drip is suffering or not doing well, I just feel like their souls or their psyche is going along with the product. I think it is, like you said, so much of them is tied up in that product, that it’s a different dynamic, even, than someone who’s a physician or a fireman and has a job that requires them to be really intense and focused. It just takes a piece of them in a different way.
Ali [00:24:26]: Absolutely. So, you mentioned earlier how Rob had left these great, salaried jobs. And was there any point at which [you] hoped he would go back to a salaried job and left all this founders stuff behind?
Sherry [00:25:34]: Not really, to be honest. Rob has done a pretty good job of, I think, assessing risk pretty well. He’s always stepped down, so when he first moved from having a salaried position to contracting, he went half-time at his salary job and did half-time consulting. And then when he moved from consulting to products, he just did this sort of slow shift. And so by the time he was all the way a consultant, or all the way an entrepreneur who was doing products, there’d been enough build-up process that I wasn’t worried about it. And I had seen that it was working before he made the leap. I think because we are so addicted to our flexible schedules, like, taking off on Fridays often, or being gone for a month when we want to, it’s been such a benefit that I enjoy so much, that I think it has helped buffer any anxiety that I might have about an instable income source or anything like that.
Ali [00:25:50]: What do you do with your patients that you see when you’re like, “Okay. I’m going away for,” because you have a very face-to-face, people rely on you, like, “Help me. I’m having an anxiety attack, and I need to talk to you right this second.” So, how do you take off time like that?
Sherry [00:25:52]: How do I abandon them?
Ali [00:25:53]: Yeah.
Sherry [00:25:53]: Yeah.
Ali [00:25:55]: Well, I didn’t mean it like that.
Sherry [00:27:02]: But they probably would think that. I try to do a really good job of just saying up front, “This is how I live my life.” I’m really committed to my work, and I’m really committed to taking care of my patients, but I am gone for four weeks, usually in the fall. And I’ve gone for a couple weeks in the summer and usually gone between Christmas and New Year’s. And I just try to tell people that when I begin to work with them, so that it’s not shocking or surprising. I also work with a really great team. I work in a clinic where there’re other therapists and other physicians, so generally the people I work with individually have at least another point of contact. So, they either have a psychiatrist, or they’re in a group therapy session, or something like that. So, I have people that help cover for me when I’m away.
Yeah, it’s hard on them. It’s hard on my patients, and it’s kind of messy. But they have consistently told me, and I believe them, I think, that they know that this is part of who I am and that they like working with me. So, they’ll deal with it.
Ali [00:27:06]: They’ll deal with it. They’ll suck it up for the month they have to talk to somebody else. Then –
Sherry [00:27:07]: Right.
Ali [00:27:09]: – as soon as you come back, they’re like, “Oh, thank God you’re back.”
Sherry [00:27:14]: It hasn’t really hurt my practice. I’ll say that. It hasn’t really hurt it.
Ali [00:27:23]: That’s good, though. That’s kind of where I’m at now. My psychologist might take two weeks off, or take a month off. We’re just like, I can’t just –
Sherry [00:27:24] I committed to these people.
Ali [00:27:33]: – Yeah. I’m like I don’t have anybody else to rely on. If I’m not there, then classes and sessions don’t run, and there’s no revenue. That’s –
Sherry [00:27:33]: Yeah.
Ali [00:27:43]: – the scary thing about being a sole proprietor. And there’s no one but me right now, so it’s all or nothing. So I’m either there making money, or I’m not.
Sherry [00:27:45]: And if you’re not there, there’s no money.
Ali [00:27:49]: There’s no money to be made. That’s kind of scary.
Sherry [00:28:30]: And it’s been interesting to see Rob and Mike do that to some extent, in that they have decided to be partners in some of these ventures. Sharing MicroConf, sharing the podcast. And I think that has been really beneficial to Rob, because he has somebody to talk nuts and bolts with that’s not me, and he has a partner in it. So, it doesn’t feel as isolating, or as scary when you have two brains. Maybe someday you’ll take on a partner or something like that, but that’s one thing that I’ve enjoyed about watching them develop over the last five years, is that they have a system of getting each other’s back and sharing the labor, certainly of planning MicroConf and things like that.
Ali [00:28:44]: Absolutely. It’s finding the right partner, too, because you just don’t want to find a partner. You want to find the right partner. I’m really thankful, too, that Mike has Rob who he can talk about all this nerd stuff with that I’m not like just “I don’t know what you’re saying.”
Sherry [00:28:45]: They speak the same language.
Ali [00:29:19]: Exactly. And I’m like, “Go talk to Rob about this stuff, because you’re speaking a different language, and I don’t know what you’re saying.” I try to do my best, but he knows I have limitations in that department. But you’re right, though. It’s nice that they have a different sounding board besides us, and it’s great that they even have built this community with MicroConf and the podcast so that there is, it’s not like a partnership in the sense that it’s two people working together, but it’s this, I don’t want to say “support group,” but it is basically a support group: “Where can I go to ask a question?” “How do I find out more about X, Y or Z?”
Sherry [00:29:35]: Both MicroConf and the Founder Café, I think, exist because people are married to people like us who are like, “I don’t know what you’re talking about.” They have filled that need and, thankfully, not had to go outside the marriage but just figured out where to find a spot to talk about these things.
You know, given that you are ten years into this relationship and so many years into being married to a founder, are there any words of wisdom that you have for other founders or their families about how to figure this life out? How to do it well?
Ali [00:30:36]: As long as I’ve known Mike, even when I first met him, he was already working on a side project. He had a full-time job, was going to grad school and was working on a product. So, I always just kind of accepted from the get-go that that was who he was. That was a part of him. That was kind of his deal. So, I think for it to work, you have to accept that about your spouse, that this isn’t just like they woke up one day and said, “Hey, I’m going to start a business today.” It’s almost ingrained in them. It’s part of who they are.
Sherry [00:30:50]: Yeah. This is who they are. And whatever business they’re working on, or dreaming up, or scheming, or doing the marketing for is like another appendage. It’s pretty intimately attached to who they are.
Ali [00:31:19]: Yeah. And asking, or expecting, or wanting them to be anything other than that is just not going to make the relationship work. And being really supportive and listening and, like you said, get that Google Calendar out and start planning how you’re going to balance everything. And communication is definitely key, because if you don’t have a good communication pattern with the person, it’s just not going to mesh. It’s not going to work, for either person –
Sherry [00:31:19]: Right.
Ali [00:31:31]: – because it isn’t going to do well, and your marriage and your family isn’t going to do well because you’re shut down from interacting or letting the other person know what you need, or what they need.
Sherry [00:32:16]: And I think, to add to that, one of the things that sounds like both Rob and Mike have done pretty well is that they have done a good job of listening to our dreams, of also using their entrepreneurial skills and their spheres of influence and investing in us the way that we have invested in them. At least in our marriage, it’s never felt one-sided. Like, Rob’s doing really cool, amazing things and has this interesting entrepreneurial life, and I’m schlepping kids around. I think both of us are really committed to the growth and well-being of each other and that my dreams are really important to him. And if I say I want to do something, he’s like, “Okay. How can I make this happen for you?”
Ali [00:32:17]: Mm-hmm, yeah.
Sherry [00:32:31]: That’s been really important, and I think that might be a little bit exceptional in the founder world, especially because the apps and starting these businesses can be so all-consuming if people aren’t doing a good job of paying attention to what’s going on with their partner.
Ali [00:32:59]: Mm-hmm. Absolutely. I would agree with everything you just said, because Mike’s been very supportive, too, of everything that I’ve wanted accomplish outside of raising kids and making dinner. Yeah, it definitely has to be a real partnership.
So, I was wondering. I know that you and Rob each take a personal retreat at least once a year each, sometimes twice a year. Is that right?
Sherry [00:32:59]: Yeah.
Ali [00:33:11]: And I was wondering how you both came up with the idea to take a personal retreat. What was the catalyst for that idea? And maybe what you guys consider a, quote, unquote, “personal retreat”?
Sherry [00:34:18]: Yeah. It’s a great question. It’s something that has been so significant in our lives. In our other podcast, on “Zen Founder,” we jus recorded, I think it’s episode 2, but it’s a whole episode about this, so you can check that out, or people can check that out if they’re interested. But, basically, we have just benefited so much from the time away from normal life. I think we started doing it when I realized that I was really unhappy in my job, and I just thought, “Oh, my gosh. I have spent years preparing for this job, and I just need to get away and sort out how am I feeling, what am I thinking and what do I want to do about it.”
So, the first retreat that was one that I went on, and it was really all about “What’s going to be my direction,” and it was so helpful, because getting away from home and stepping outside of the routine really allowed me to think pretty clearly.
We didn’t come up with this. There’s lots of material about how to do retreats. And –
Ali [00:34:22]: Yeah, I grew up Catholic, and going on retreat was just what you did.
Sherry [00:34:24]: – yeah, it’s a regular process.
Ali [00:34:24]: Yeah, yeah. But you go and pray. So, the whole idea of a personal retreat, I was just like, “Hmm. What’s that like?”
Sherry [00:34:34]: So, I go and go on walks, or –
Ali [00:34:37]: Think.
Sherry [00:34:51]: – right. But it’s the same kind of process. It’s that silence, a more quiet, subdued environment to look inside. So, it’s probably similar to your retreats as a child, but maybe less guilt-ridden.
Ali [00:34:54]: Less time on your knees, praying, maybe more of reflection.
Sherry [00:34:56]: More time drinking wine on the beach.
Ali [00:34:58]: Now you’re speaking [crosstalk].
Sherry [00:35:06]: Like that. Check out that episode. You might like it. It talks about how both of us have used them in slightly different ways.
Ali [00:35:19]: Okay. Yeah, I definitely will. So, do you have a special place that you go to do those retreats? Or, do you change the location of the retreats depending on what you need for the retreat, or what you’re looking for out of it?
Sherry [00:36:03]: Yeah. We have done different things. We live about a little over two hours from the Central Coast of California, which is a really beautiful, lovely area. So, we generally go there. The last one I went on, I went to the Santa Cruz Mountains. So, I wasn’t on the beach, I was just in the mountains in a cabin. Other times, I have just stayed in a nice hotel by myself, because I wanted a bubble bath in front of the fireplace, things I don’t get to do at home. We set aside some money and plan to do something that is really in line with whatever either of us is feeling like our vibe is at that time.
But, you certainly don’t have to spend a lot of money. You could go camping, if you like to go camping. I don’t like to go camping. That’s not restful to me.
Ali [00:36:04]: I don’t like to go camping either.
Sherry [00:36:05]: – so, no camping for us.
Ali [00:36:08]: No camping. That is not my idea of vacation or fun.
Sherry [00:36:10]: It’s a lot of work.
Ali [00:36:15]: It is a lot of work. I’m like, “This quest sucks. I’m not doing this anymore.”
Sherry [00:36:23]: Yeah. Send me to the hotel that has the wine bar and the nacho bar, and that’s pretty much what I do.
Ali [00:37:06]: That’s an awesome retreat. I can get down with that. You know, Mike and I have talked about it, and he had suggested it. I actually did one. I just checked myself into a hotel for a weekend. And Mike started doing a couple. He’s done, I think, one or two. But they really are nice. They’re just a nice break from reality, almost. I can just go and be alone and focus on what is it I want out of life, or to pursue next. Or, how am I going to build out from here? Would you say that that is really an important component to being a[n] entrepreneur, having that time?
Sherry [00:39:04]: I really think so because no one is telling you what to do. Right? No one is telling you whether to sell your app or grow your app. No one is telling you what to launch or not launch, or what features to add. And no one is telling you what kind of life you’re going to have. You’re not working for a corporation that says, “This is what’s possible for you.” Everything is possible. And so much of your life is determined by what you want, but I think the frenetic nature of doing a startup makes it very difficult to really check in and ask the question “What do I want?” “What’s going on in my life?” “What are my goals,” beyond just responding to bug fixes and customer complaints. Especially once you’ve got something going that has some momentum, you can just sort of coast on that for a long time.
And so I feel like taking a retreat as a founder is foundational. It’s essential, because how else do you know what the hell you’re doing? Like, how else do you know what your life is going to be like? And I think people who don’t have any mechanism for introspection can easily drift really far away from who they want to be and how they want to be living. And the retreats, for me, just totally reset me.
Well, we should, I guess, probably move to wrapping it up. But maybe if this isn’t too weird, I can actually say something to Rob and Mike, and that’s that we are really proud of you and really impressed with what you’ve done with the last five years and really proud of the community that you two have built together and proud of the way that you’ve handled yourselves and grateful for the good partners that you’ve been to both Ali and I.
So, congratulations on five years. We are very excited for what the next five years will bring, and whatever it brings, you know that you have partners who are super supportive and love you both very much.
Ali [00:39:07]: And we’ll, hopefully, make it to MicroConf someday.
Sherry [00:39:12]: And maybe all four of us will meet at some point in person.
Ali [00:39:13]: That’d be nice.
Sherry [00:39:15]: That could be your five-year goal, Ali.
Ali [00:39:28]: That is my five-year goal. You know? That’s my five-year goal is to make it to MicroConf and actually meet Rob and Sherry face-to-face so I have some faces to go with the names that I hear so much about.
Sherry [00:39:33]: That would be fun. Cool. Well, you want to
Ali [00:39:39]: And then we can all tell embarrassing stories about what Rob and Mike were like in their younger years, and that’s always a good time.
Sherry [00:39:46]: If we come on again in the next five years, we’ll just make it a total roast, like, all of the embarrassing stories that we don’t want to say yet.
Ali [00:39:49]: Oh, so fun. So fun. I’m in.
Sherry [00:39:52]: Sounds good.
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