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Show Notes
In this episode of Startups For The Rest Of Us, Rob along with co-host Tracy Osborn answer a number of listener questions on topics including two side marketplaces, automated testing, building like-minded relationships and more.
Items mentioned in this episode:
Rob: Welcome to this week’s episode of Startups for the Rest of Us. I’m your host, Rob Walling. Each week on the show we cover topics relating to building and growing startups in order to provide yourself with a better life. These are not the typical Silicon Valley startups where fundraising can be a goal on itself, where people sometimes overwork themselves, 90-hour weeks, and where building slide decks are often valued more than building real business.
On this show, we’ll talk about building software companies and that can be Software as a Service, WordPress plugins, Shopify add-ons, Photoshop add-ons, even downloadable software, mobile apps, whatever. There are many, many ways just there to step your way to a business that can provide you with a better life and better existence.
A common thread over the past nine years in the show is that your product or your company is built around being a human being and having goals around on what you want to accomplish as a human rather than the business being me and be all of all your achievement.
There are three main things that we’ve espoused for the past 449 episodes of the show. It’s things like freedom. It’s the freedom to work on what you want, when you want, without a boss breathing down your neck, or the freedom to go to your kid’s baseball game on a Thursday afternoon without asking permission.
Its purpose is the ability to work on something that fascinates you and it drives you every day to make it better. The purpose of building something that tens of thousands of people get value out of, that makes you feel great and proud of what you built, and it’s about relationships; deep, meaningful relationships with your family, your significant other, your kids, maybe even have time for friends.
That’s Startups for the Rest of Us is all about. That’s what it’s always been about. It’s the lens through which we view startups and that’s why we say, it’s for the rest of us.
We have a few formats for the show. Sometimes, we talk through a topic in detail, we work through an outline of how to do a particular tactic, sometimes it’s purely for inspiration, sometimes it’s to help you grow your business over the next week or two, something you can implement.
Sometimes more rarely, we do interviews with folks who can offer advice or inspiration. In other times like this week, we answer your questions. What I like about answering questions live on the show is not only can I directly help a founder who has an issue, not only can I directly help a founder who has a question or challenge or something they’re trying to overcome, but you as a listener, can either learn from that thought process, learn from that answer, and hear how someone thinks through hard decisions. Being a founder is about making decisions when we don’t have enough information. Took me a long time to realize that.
Being a founder is 70% mental and so much of it is about doing things that are hard, that are scary, and that you don’t have enough information to make a 100% correct decision. All of that to learning scale and it’s something that I hope you’ll be able to learn from the show over the years.
I’m here today with my co-host, Tracy Osborn. She was the founder of WeddingLovely and now she’s my colleague, friend, and program manager here at TinySeed. Welcome to the show, Tracy.
Tracy: Thanks for having me.
Rob: Excited to have you on. Beyond being a program manager at TinySeed and as I’ve mentioned having run a startup, a two-sided marketplace for wedding services called WeddingLovely, Tracy is a Python developer, she’s a gifted designer, and an author. She’s written several books that help make tech friendly for designers and design friendly for developers. Is that right? Am I saying that right?
Tracy: Pretty much, yeah. Tech is a scary subject and it’s been a fun topic to write on; what can I do to help people jump into it.
Rob: Absolutely. All of that is available, more on Tracy is available at tracyosborn.com and you’ll be hearing more from Tracy in the coming months. We’re working on a lot of fun stuff together.
Tracy: Yeah. The stuff at TinySeed has been so much fun and I’m really happy to be a part of the team.
Rob: Yeah. Us as well. We love having you. Let’s talk through some listener questions today. I know we have some voicemails and we have some text-writing questions. Typically voicemails go right to the top but today, I think we’ll start with some emails.
Tracy: Funny listening to your previous podcast on this. I was like, “Ooh. We’re going to switch up the formats, jump into one of the […] questions.”
Rob: Indeed.
Tracy: Let’s start with this one from Chris Palmer. He got a co-founder that is an experienced software engineer, and his question as a designer/product person, he wonders if there’s too much testing. How much time of the software build should go to things like unit testing, snapshot testing, et cetera, for an early-stage production product. So, he says, “Rob, when you had Drip, what did your engineering team do?”
Rob: This is a good question and what I like about this is, if you’re not technical, if you’re not a developer, it’s easy to discount unit testing. He’s talking about snapshot testing and all the types of automated testing, integration testing. There’s so much you can do and I have seen Software as a Service companies have to rewrite their entire codebase or literally run into major problems scaling because they skipped this in the early days.
Unit testing in particular, I am such a proponent of having 80%, 90%, like really extensive unit test coverage. I think if you’re a non-technical founder working with a technical co-founder who is saying “Hey, it’s going to take longer because I have to write a unit test,” that part, I’m all on board with.
Where it starts to become a gray area for me is when we talk about snapshot testing, which is taking a screenshot and comparing it from one build to the next to make sure that things aren’t going wrong, where we talk about full end-to-end integration testing, actually hitting the UI, hitting a web interface, clicking buttons, and doing all that stuff.
I would love and would have loved to have had all that testing in all of my startups but it’s very, very, time consuming and that has tended to be where I’ve drawn the line, is anything passed unit and some minor integration testing and smoke testing of API endpoints, all that stuff, we would build because it’s code and developers can get in the flow, they can hammer it out, and you get this amazing test coverage.
I used to brag about when we’re going to be acquired and then when we were hiring for new developers, I would say, “We have 2.5 lines of test code for every line of production code.” Some developers realize that’s not actually that outrageous. That’s probably where around where you should be if you really have good test coverage. But it sounds crazy to a non-developer like, “Woah. Haven’t you wasted a bunch of time?” but you haven’t. So, for me, that’s where I draw the line in the startup, where I am trying to move quickly, trying to go for end-to-end UI tests that cascade down through everything, I think is overkill. This is where it can be personal opinion.
Now, if I work for a bank, if I work at a Fortune 500 company, I would probably go to that next level because downtime and failures are catastrophic. You work at Amazon, you work at NASA, there are certain places, medical devices, where you do have to take that testing to the 99.999% non-failure rate. You can’t fail.
When you’re building a startup, you’re trying to grow, you’re trying to move fast. You can fail. You don’t want to, but you can fail a couple percent of the time. 1%, 2% of the time, where one of a hundred deployments has a bug in it. One out of even, frankly, 20 deployments will probably have some type of minor bug in it that you’re not going to catch but it’s going to save you dozens, if not hundreds and hundreds of developer hours along the way. That’s my take.
As a developer yourself, do you have a take on it?
Tracy: Yeah. It’s funny because my background is on design and I picked up Python programming. When I was building my first few web apps, I never did any testing at all, because I was like, “Oh. Why should I do this? I can just poke through the website and figure things out.”
But a little bit of time spent on writing those tests in the beginning, will hopefully prevent any kind of horribly stressful terrible moment later on when things go down, when the bug is found and everything. You don’t want to have that happen in the middle of the night. So, a little bit of time is going to save you a ton of time later. It’s just not going to feel like that in the beginning.
Rob: That’s the way to think about it. At a certain point, when we hit scale, and I believe it was post acquisitions, we had thousands of paying customers and I think, if we have the free plan, it was tens of thousands of people using it. This is Drip, of course.
We did talk about implementing end-to-end, front end snapshot testing in that sense, but it was only going to be for one or two flows. It was going to be the sign-up flow and something else critical, like sending a broadcast email because we knew that those two flows people use all the time, and if one of those failed, then we have a real problem.
Tracy: That’s a good point, actually. If you look at what are the critical flows are, when it comes to payments, or registration, or whatnot because when you’re launching new features later on, you want to make sure when you add those features, you can run those tests and make sure you didn’t inadvertently break those flaws.
Rob: Exactly and that’s the thing. For Chris, the original question asker, the thing to think about is how well do you know your co-founder? Does your co-founder tend to be extremely conservative? Does he or she come from a Fortune 500 company, or a bank, or NASA, or Lockheed, or somewhere where they had to have ridiculous test coverage that can never fail? Or have they worked a lot on startup environments? And what’s their personality like? Did they take it fast and lose? Did they hack stuff together? Their PHP hacker used to do it on the weekend and they never do the official stuff. They’re really tight knit unit testing ideas, or are they somewhere in the middle?
I think that almost counts for a lot and to be honest, I trusted my co-founder, Derek, a lot in the early days. I said, “Look, right unit test. Of course, we need them, we’re absolutely doing it,” but I let him go from there. I didn’t come in and say, “Oh, we should have this tested and that not tested.” I trusted his judgement that he’s conservative enough, that he was stressed that things are going to break about the same amount that I was. He wasn’t overly stressed nor too lax […] to cool with it. So that wound up being a pretty good relationship there.
Tracy: Cool. Should we move on to the next question?
Rob: Indeed.
Tracy: All right. This question comes from Tom, the founder of Tom’s Planner. He started working on this in 2007 and though the current design of the product itself dates back to that year, though it had a significant update years years ago, but starting to feel outdated again. So, he’s looking at doing another redesign.
He says, “Now, I have four designs to choose from. Each has their own strengths and weaknesses. I really like one of them. I decided to be a good idea to pull my most active users about it as well. That’s where the problem started. The users prefer another design than I do. Even worse, they scored the design I like the lowest. So, now what?”
He says, “Going with the majority would make sense but there’s a couple things to consider.” He really likes the other design. The design that the other users scored best, looks most like the current design that we have now and I’m guessing that’s part of the reason why it’s doing so well. People don’t like change. The design that he likes most has a timeless quality to it, which he believes, which is important to hand but the users probably don’t take that into account and the users are quite divided over it. Even though there’s a winner, no design had a bad finished. “Am I inclined to, despite the results of the poll, choose the design I like best and think this most future proof, but since it is the design users like least, I am still in doubt. Any advice?”
Rob: This is a tough situation you’ve gotten yourself into, Tom. I feel bad for you because I feel like asking users their opinion is pretty much not something that I would recommend overall. Tracy, you run a wedding marketplace, for wedding services. You had consumers like brides and grooms who are buying from service providers. Did you ever ask or poll your users for specific opinions like this?
Tracy: I did not for the site itself but there was an aspect of WeddingLovely where people could have their own wedding websites. I let users have the choice of emailing me and asking me for a custom design and that was a terrible, terrible thing to do. I end up ripping that out because I got overwhelmed to feedback and people were choosing and asking for things that I thought were bad design and didn’t reflect the brand. I end up actually removing that feature entirely.
So, I’m very strongly in the camp that I would prefer not to talk to my users about designs because, as Tom mentions, it can make things really complicated and I also worry about what would happen if you launch a design and it’s not the ones that someone wants. What would happen with the person who voted for the design? What would they feel? It’s a very sticky situation.
Ro: Yeah. People can be really opinionated about things that they’re not experts in. That’s an issue. Design is not something that we all have a training in. I don’t hire the person down the street to correct my back or to do surgery on my knee when I had knee surgery. I hire people with expertise. I don’t go down the street and hire a 15-year-old kid to write code for my website, although, he probably could. I hire people who have experience, and expertise, and training, and knowledge in the space. Design is the same thing.
Everybody has opinions but do they have taste? It’s an interesting thing and I don’t want to make it out like being snooty like, “Oh, I have taste because I only drink refined wines and these very pretentious single source origin coffees,” which my brother does and I say, “We’re going to go to the pretentious coffee place or go to the cheap one?” Of course, the pretentious coffee taste better but it’s $15 a cup.
I think if it’s all designers and you really want to get opinions and feedback, then do that. I think it’s more trouble than it’s worth, and I think it will create problems every time because what’s funny, as Tom said, that his users picked the one that’s most similar to what they already have because people don’t really like change and they don’t like using new software.
If you know that in 2007, 12 years ago, that you designed this thing, that design probably isn’t going to last in another 10 years. You want this one to at least another 5 or 10 years. If I had been in Tom shoes, I would not have done this. We would ask for opinions about, “Hey, we have some features. What do you think about this or what feature doesn’t this software do?” Those are interesting things because those are actual things that they’re doing in day-to-day business and they are experts on their own work flow and on their own needs for a product. But asking what color the button should be, or how a page should look, or showing three designs for a page, aside from just pure use ability things, like “Wow. I’m totally lost. I can navigate this,” that makes sense, but there are opinion on whether there should be a drop shadow or not, or a font. That’s why I hire experts or become an expert yourself, I guess.
Tracy: There is another piece of this puzzle that’s missing, which is that in a redesign, […] the user experience, not just the interface. When you’re asking people, it doesn’t really say about how we ask for feedback on the design and presuming it’s screenshots and that’s leaving out how the interaction actually is.
The users might be choosing something that looks like the old design because they don’t want the placement of buttons and how things work underneath the change. The thing that I struggle with new design is I’m trying to figure out how things are going to work and who might be scared about changing the system.
When one is doing a redesign, I think it’s important to include how things work and try to improve those flows about how someone uses the website, how someone signs up, or ask for payment information, whatnot. You don’t get feedback on those things when you’re sharing screenshots. So, that could be another thing for Tom to do, is do another round of feedback but not by users but go cray away of testing out the interactions about how things are working and see if his new design does better on that aspect. Does that make sense?
Rob: Yeah, it does. He did do screenshots. He included a link way at the bottom that has a link to the screenshots. One of them doesn’t work but the other one says he has all four designs and frankly, they’re all pretty similar. I actually don’t think it matters which one he goes with.
Tom, my advice would be don’t do this again because having trying to do it by democracy. If you have a product, you should have a pretty strong opinion and a vision for your product, I think. If you want to do a fun contest or a competition, that’s fine. But if really, it’s something as fundamental as the design of your product, that’s where you have to be.
You’re the founder, you’re in charge. You can certainly ask some opinions with people that you trust. You can get two or three designers together at your company. You can get people who have expertise to weigh in. When I was designing or having the TinySeed website designed, I asked a couple people that I know that are really good designers, that have a really good eye for fonts, and this and that, and I trust their opinions. But I didn’t go post it somewhere and ask for the opinions of everyone on my email list because I just don’t think that’s that productive.
Tracy: It’s just going to be a lot of noise and a lot of confusion, probably a lot of stress. It’s such a qualitative product. You don’t have any numbers to bring it back on to and that could be something. Also, when you’re choosing in a redesign, if you can do A/B testing of some sort, maybe on smaller elements, you’ll be able to say, “Okay, this one definitely works better.” More people are signing up or doing something that you want them to do because you can tie that to numbers but with just asking someone’s opinion about what looks better is not going to give that much useful feedback.
Rob: I hope that was helpful, Tom.
Tracy: Sorry, Tom.
Rob: Good luck. Our next question is a voicemail about which side to focus on when building a two-sided marketplace.
Chris: Hey, Mike and Rob. This is Chris Bowles from Kentucky. One of the […] for TinySeed, first batch. My question is relating to chicken or the egg with SaaS B2C/B2B. Got a startup concept that I’ll actually be providing free trial on the B2C side with a very small revenue figure to help support the B2B side.
Without going into a bunch of detail, basically I’m in stealth mode right now. How do you know whenever you recruit the majority of your revenue through the B2B side or you provide the trials to the B2B side versus beginning free trials on the B2C side? How do you know who to market to first and to who to set up on the website prior to launch to be sure everybody […] on […] day? Thanks for all you do. I’ve learned a lot. Have a good one.
Rob: Okay. It’s an interesting one. I think you’ve gone a little into the wood with the free trial and that kind of stuff. I just think about this as a two-sided marketplace, and there’s a business and a consumer side. My translation of his question is which side do I need to bring to the site first? You’ve built a two-sided marketplace?
Tracy: Yeah. The chicken and egg problem is tough because you need to have enough on both sides of the equation for your website to be useful for both. With WeddingLovely, it was a marketplace for wedding businesses and that was the primary focus. There was a consumer side where there’s a planning application. My recommendation is to focus on the businesses.
My personal experience with WeddingLovely is I actually the site very early on which is a few businesses because I needed to have something online for these businesses to say, “Okay. This is launched.” I’ve seen other people using it and I even told those businesses like, “Hey, this is something that’s going to be a slow growth thing.”
In the beginning we might not be able to send them a bunch of consumers, but I was live and they’re listing to the site for free. By focusing on the businesses, they actually help my marketing a ton because I was able to work directly with the people that were on the website with WeddingLovely. They had their own network, social media, blogs, and whatnot. So, they helped build up that consumer side of the business while I focus most of my effort and intention on the business side.
It was a […]. Market places take a long time to build up both sides but I’m a fan of working, I mean, businesses are also easier to work with, by far. I think there’s going to be a lot more benefit through focusing on the business side. What do you think?
Rob: I would focus on the business side first, in that case. I would basically have a landing page somewhere, or a social media account, an Instagram account, or something that is posting amazing stuff and trying to forget this consumer side. Some type of traction so that I don’t have to start from zero. Once I have 10, 20, 30 businesses lined up, I at least have an email list of a hundred people, or I have a thousand Instagram followers, or something there.
Typically, what I say when people ask about how to setup a market place is focus on one side first and in almost all cases, it’s pretty obvious which side you need. If you had a bunch of consumers with WeddingLovely, and you’re like, “All right. I have 5000 people who wants services,” and you have zero services, you have zero businesses, there’s no business there. So, you have to bring the businesses first.
The challenge is, of course, you have to bring the businesses to a place where you don’t have any consumer audience. You could then step back and say, “Well, should I start a blog, or a podcast, or an Instagram following, or an email list, or something that gets the brides- and grooms-to-be?” then from there, say, “Well now, I have this email list of 20,000. Now, I go recruit businesses?” That could be one way to do it. That’s another way to think about it. But you’re starting on a cold stop on both ends, right?
Tracy: Yeah. Chris mentioned that he was in stealth mode. I think that’s something that should depend on what he’s working on, but I feel it needs to be something that you have to get out of stealth mode so you can start recruiting people on either side of the audience.
Rob: Yeah, I would agree. Everytime I hear stealth mode, there’s certain yellow flags, red flags are probably stronger, but stealth mode is one here, “I want to raise money from you. Sign an NDA. I’m building a startup that targets every small business in the United States. It’s any business and there’s 60 million of them, that’s my target audience.” There’s just certain things that’s like, “Yeah. You’re making a basic mistake,” in almost every case.
Typically, the people who make stealth mode work are these really experienced founders. Ev Williams can do stealth mode. He’s done Blogger, and Twitter, and Medium, and on and on. He can do what he wants and break the rules. Steve Jobs can do stealth mode. There’s a handful of people that can do it, pull it off, and it works. But honestly, if it’s your first one and trying to figure stuff how, don’t do that. Just get out there. You need to start generating interest on both sides of this. I agree. I would start at looking at getting businesses on board and having conversations.
Here’s the thing I would do. Whatever it is, if I can bring you 500 customers a year or 10 inquiries a month, or whatever that number is, is this of interest to you and is this worth $99 a month for you to subscribe? That’s your customer development. You have to do it in theoretical because you don’t have that other side of it yet. If they say yes, then awesome. Get on the waiting list, there’s no commitment now, let me get your info, and then you go to the other side and you either start running ads, or you start SEO, or you start social, or you start whatever it is that’s going to bring that consumer side, and you start funneling them somewhere.
You don’t need to write a bunch of code to do this. You can funnel them to a blog, funnel them to a landing page, you can funnel them to a hacked together WordPress site that has a couple of listings that you literally put together by hand. I mean, all this stuff can be done with just hustle. You don’t need to go pay $50,000 for developers to go build anything. You’re just trying to test it out. You’re trying to push it forward a piece at a time.
Tracy: This is a great place to things that don’t scale. For those businesses, what can you do by hand for each of those businesses in the beginning just to start getting the ball rolling.
Rob: Indeed. Thanks for the question Chris. Hope that was helpful.
Next question is another voicemail. It’s about connecting with other founders to build relationships and he’s referring back to a comment I made a few episodes ago.
Michael: Hey Rob and Mike. This is Mike Whitbeck, one of the co-founders of UberWriter. We worked in the mortgage space and we built some income calculation software. We’re on our 5th year of business and I’ve listened to hundreds of your episodes. One of the co-founders, David Stamm, and myself have used a lot of your advice of the podcast to help reguide and redirect our business in very successful ways. Our website is www.uber-writer.com.
On episode 444, I believe you mentioned that you and your wife, for about the feelings of isolation, have other entrepreneur couples over maybe once a month or have dinner with somebody just to talk to people that you relate with. Though it’s probably a little bit weird and just trying to figure this out is, I know I’ve run in the past where you introduce yourself to another couple, just basically go out to dinner, a movie, or a common event with them, and maybe you just don’t kind of hit it off. I guess the awkward question is, when you meet up with these people, is it generally an expectation that you’re going to meet again or you just let the friendship go or not go where it goes? How do you handle that? Enjoyed the podcast. Please keep it up. Have a great one guys.
Rob: This is an interesting question. I think there’s a couple of things. One for me, when I was younger, I felt like I had the need to be best friends with people or not friends at all. It’s just a very binary thing. I’m talking like junior high and then high school. That’s how I was raised. That’s how my family did stuff. It wasn’t until probably after college where I realized, “Oh, having other friends who you just hang out with and aren’t necessarily your best friend or it’s not this binary thing, but you can hang out with them now and again, once a month, once every other month, you see them. It’s nice, but that’s it,” is a good thing. I think it’s a good thing for all of us to have larger networks than just one or two people. Not a requirement, but it gives me accessibility to more people to go see Avengers: Endgame when I need to and I’m not just relying on one or two people. That’s the first thing.
The second thing is when we invite people over, we literally just say, “Hey, we’re having a couple of people over that we know. We’re all startup founders and we’d love to have you over.” That’s the expectation. In addition, we tend to invite two couples or three couples over. That helps it not be awkward if, for some reason, there is one person in the group can be whatever. Talk too much, not talk enough, be a train wreck, whatever, and that won’t ruin the thing because you have six or eight people there. Whereas, when it’s just a double date, you really are reliant on the personalities of the folks around you, and that, of course, can be a wildcard.
So, there’s strength and numbers there and there’s really no expectations beyond that. We say, “Hey, we do this a few times a year and we have people over blah, blah, blah,” and that winds up being the situation. It worked out well for us. So far, we haven’t had any of those situations where it’s actually been bad or awkward. We haven’t become best friends with everyone, but that’s okay. That wasn’t the expectation up front anyway, neither from us nor the other side. It’s just a natural conversation about random stuff.
What’s been interesting is some of the funniest conversations have not been about our companies, have not been about our businesses. It’s been topics surrounding fact. Just that startup founders tend to be creative, driven, motivated, smart people, who are perpetually learning, and just being in a room with those kinds of people and asking what shows they’re watching, what kombucha you’re drinking, what’s the best coffee place you go to, what conferences you like right now, what books are you interested in, what podcasts do you listen to.
This stuff is all tangentially related to work but we’re not sitting there analyzing each other’s businesses, giving us advice on pay-per-click ads and positioning. It’s much more this almost social conversation. What I find is that when I’m talking to, again, interesting, driven, smart people who are shipping things, it just tends to be better conversation no matter what we’re talking about.
Tracy: This question really resonates with me. I don’t know if you had the same issue when you moved to Minneapolis. I’ve moved to Toronto about three years ago and I left all my old friends behind. When I moved here, I wanted to jump in and make friends that I think also do the same thing I do so we can have conversations. It’s been a hard slog. It’s really hard to make friends as an adult. Tying it to a business is even harder. So, I really like your suggestions and I think I learned something from this. I’m going to try to do a little bit more social stuff.
One thing I wanted to mention was, one of the best parts about just meeting up with people, not having a lot of expectations, and just hanging out, especially if you’re a founder. You’ll probably going to see them at the networking events in your city or around the world, or wherever you go, and just making those small connections. They’re not going to be best friends, like you said, but then making these small connections can be really fun because you’re going to see them later on. You’re in continually reinforces connections overtime and I think it’s really great to have these people.
For me in Toronto, I have people I see. Probably it’s just simply at events and they’ve been over at my house one or two times. It’s been really fun to start making those relationships and for a few people it has. Eventually, it’s going to move into, “Okay. Cool. Let’s talk business. Maybe I can tell you a problem I’m having. Maybe get some advice.” Just starting out and meeting people for the first time, don’t worry about talking business. Just see if they’re a good fit for you and not that everyone’s going to be.
Rob: I completely second the notion of how hard it is to make friends as adults and I don’t know that anyone ever told me that when I was growing up, but it just seems like you made friends in school, then you made friends in college. Shortly after college, if you’re still around those friends it was easy, but moving to a new place or relocating is hard.
I’m actually thankful because Sherry is pretty deliberate about wanting to find a community in various aspects of our lives. That has caused her to essentially just start making lists of people that we meet anywhere. We go to a meet-up, I did a little talk here locally a few weeks ago or any of the mirative startup events. Anybody we find that’s interesting, she’s like, “Get their names, get their email, and we’ll put them on this list.” We have this Google Doc of people now that is literally just a grab bag of some people we know relatively well and others we don’t, but we’re interested in getting together with them. We introduce them to one another often, which is cool. It’s not like our goal is to get everybody to network, but that at least there’s some value to everybody.
Tracy: Yeah. Think about talking to your 15-year-old self, being like, “When you’re an adult, you’re going to have spreadsheet of potential friends.”
Rob: And you’re going to have to invite them over for dinner. That’s just how it goes.
Tracy: I just have one more thing. Another thing when I moved to Toronto is that I insisted on working from a coworking space. That was also to get more business friends by working together and being around these people. There’s a lot of people at this coworking space after the last year, so have I grown into friends, we’re talking of business ethics because we’re there working together. I used to work at home in an office and this has been really great for me socially. It’s been really great for me careerwise, just to be around people while I’m working and then you have that little back-and-forth chit-chat. Then it grows into who am I going to invite over for dinner and doing dinner party or whatnot.
Another option that I usually recommend to a lot of people who are working solely from home is if there is a place so they can also try to make friends through coworking spaces, you might be able to build those relationships.
Rob: Literally, once a month, once every two months, it’s not that big of a burden. Frankly, you can couch it as, “Do you want to come over? We will literally order take out.” You really don’t have to cook for them. There isn’t an excuse. I’m talking to the listeners more than you Tracy.
There’s literally no excuse not to do this because when we brought this up before, I’ve had people say, “Wow. That sounds like a lot of work. I don’t think I have time for that.” We have three kids who go to three different schools. We homeschool one of them. Talk about not having time, my wife and I both work full time and do that. And yet we do this. It’s because we prioritize it. It’s not because it’s easy. Sometimes, we’ll do take out or we did potluck last time, where we provided the main thing that I grilled and people brought a salad, and this and that. It’s very little work for us.
The other thing is everybody brought their kids and they all played in our basement. Nobody needed to get sitters because that’s another hassle and expense. Frankly, it is finding sitters who are reliable and all that. There are ways to do this if it’s something that you’re motivated to do and that you think is valuable.
Tracy: Just like setting up a whole dinner party. Even just being proactive about inviting people to lunch. Maybe you said it personal goal of that twice a week, you invite a person to go on a lunch with you. Maybe you’re already at work, you don’t need to get a sitter for that, it’s a very low stress situation. That’s something my husband does and he does it way better than me. Every week, he has a different person he goes to lunch with. That’s how he creates and also build those connections.
Rob: Yep. So, thanks for the question. I hope that was some helpful food for that.
Thanks for listening to this week’s episode. Hope that was helpful to hear. Tracy and I talking through listener questions. If you have a question for us, you can call it into our voicemail number. It’s 888-801-9690. You can always email us at questions@startupsfortherestofus.com. We’ll talk to you soon. Thanks for listening.
On this show, we’ll talk about building software companies and that can be Software as a Service, WordPress plugins, Shopify add-ons, Photoshop add-ons, even downloadable software, mobile apps, whatever. There are many, many ways just there to step your way to a business that can provide you with a better life and better existence.
A common thread over the past nine years in the show is that your product or your company is built around being a human being and having goals around on what you want to accomplish as a human rather than the business being me and be all of all your achievement.
There are three main things that we’ve espoused for the past 449 episodes of the show. It’s things like freedom. It’s the freedom to work on what you want, when you want, without a boss breathing down your neck, or the freedom to go to your kid’s baseball game on a Thursday afternoon without asking permission.
Its purpose is the ability to work on something that fascinates you and it drives you every day to make it better. The purpose of building something that tens of thousands of people get value out of, that makes you feel great and proud of what you built, and it’s about relationships; deep, meaningful relationships with your family, your significant other, your kids, maybe even have time for friends.
That’s Startups for the Rest of Us is all about. That’s what it’s always been about. It’s the lens through which we view startups and that’s why we say, it’s for the rest of us.
We have a few formats for the show. Sometimes, we talk through a topic in detail, we work through an outline of how to do a particular tactic, sometimes it’s purely for inspiration, sometimes it’s to help you grow your business over the next week or two, something you can implement.
Sometimes more rarely, we do interviews with folks who can offer advice or inspiration. In other times like this week, we answer your questions. What I like about answering questions live on the show is not only can I directly help a founder who has an issue, not only can I directly help a founder who has a question or challenge or something they’re trying to overcome, but you as a listener, can either learn from that thought process, learn from that answer, and hear how someone thinks through hard decisions. Being a founder is about making decisions when we don’t have enough information. Took me a long time to realize that.
Being a founder is 70% mental and so much of it is about doing things that are hard, that are scary, and that you don’t have enough information to make a 100% correct decision. All of that to learning scale and it’s something that I hope you’ll be able to learn from the show over the years.
I’m here today with my co-host, Tracy Osborn. She was the founder of WeddingLovely and now she’s my colleague, friend, and program manager here at TinySeed. Welcome to the show, Tracy.
Tracy: Thanks for having me.
Rob: Excited to have you on. Beyond being a program manager at TinySeed and as I’ve mentioned having run a startup, a two-sided marketplace for wedding services called WeddingLovely, Tracy is a Python developer, she’s a gifted designer, and an author. She’s written several books that help make tech friendly for designers and design friendly for developers. Is that right? Am I saying that right?
Tracy: Pretty much, yeah. Tech is a scary subject and it’s been a fun topic to write on; what can I do to help people jump into it.
Rob: Absolutely. All of that is available, more on Tracy is available at tracyosborn.com and you’ll be hearing more from Tracy in the coming months. We’re working on a lot of fun stuff together.
Tracy: Yeah. The stuff at TinySeed has been so much fun and I’m really happy to be a part of the team.
Rob: Yeah. Us as well. We love having you. Let’s talk through some listener questions today. I know we have some voicemails and we have some text-writing questions. Typically voicemails go right to the top but today, I think we’ll start with some emails.
Tracy: Funny listening to your previous podcast on this. I was like, “Ooh. We’re going to switch up the formats, jump into one of the […] questions.”
Rob: Indeed.
Tracy: Let’s start with this one from Chris Palmer. He got a co-founder that is an experienced software engineer, and his question as a designer/product person, he wonders if there’s too much testing. How much time of the software build should go to things like unit testing, snapshot testing, et cetera, for an early-stage production product. So, he says, “Rob, when you had Drip, what did your engineering team do?”
Rob: This is a good question and what I like about this is, if you’re not technical, if you’re not a developer, it’s easy to discount unit testing. He’s talking about snapshot testing and all the types of automated testing, integration testing. There’s so much you can do and I have seen Software as a Service companies have to rewrite their entire codebase or literally run into major problems scaling because they skipped this in the early days.
Unit testing in particular, I am such a proponent of having 80%, 90%, like really extensive unit test coverage. I think if you’re a non-technical founder working with a technical co-founder who is saying “Hey, it’s going to take longer because I have to write a unit test,” that part, I’m all on board with.
Where it starts to become a gray area for me is when we talk about snapshot testing, which is taking a screenshot and comparing it from one build to the next to make sure that things aren’t going wrong, where we talk about full end-to-end integration testing, actually hitting the UI, hitting a web interface, clicking buttons, and doing all that stuff.
I would love and would have loved to have had all that testing in all of my startups but it’s very, very, time consuming and that has tended to be where I’ve drawn the line, is anything passed unit and some minor integration testing and smoke testing of API endpoints, all that stuff, we would build because it’s code and developers can get in the flow, they can hammer it out, and you get this amazing test coverage.
I used to brag about when we’re going to be acquired and then when we were hiring for new developers, I would say, “We have 2.5 lines of test code for every line of production code.” Some developers realize that’s not actually that outrageous. That’s probably where around where you should be if you really have good test coverage. But it sounds crazy to a non-developer like, “Woah. Haven’t you wasted a bunch of time?” but you haven’t. So, for me, that’s where I draw the line in the startup, where I am trying to move quickly, trying to go for end-to-end UI tests that cascade down through everything, I think is overkill. This is where it can be personal opinion.
Now, if I work for a bank, if I work at a Fortune 500 company, I would probably go to that next level because downtime and failures are catastrophic. You work at Amazon, you work at NASA, there are certain places, medical devices, where you do have to take that testing to the 99.999% non-failure rate. You can’t fail.
When you’re building a startup, you’re trying to grow, you’re trying to move fast. You can fail. You don’t want to, but you can fail a couple percent of the time. 1%, 2% of the time, where one of a hundred deployments has a bug in it. One out of even, frankly, 20 deployments will probably have some type of minor bug in it that you’re not going to catch but it’s going to save you dozens, if not hundreds and hundreds of developer hours along the way. That’s my take.
As a developer yourself, do you have a take on it?
Tracy: Yeah. It’s funny because my background is on design and I picked up Python programming. When I was building my first few web apps, I never did any testing at all, because I was like, “Oh. Why should I do this? I can just poke through the website and figure things out.”
But a little bit of time spent on writing those tests in the beginning, will hopefully prevent any kind of horribly stressful terrible moment later on when things go down, when the bug is found and everything. You don’t want to have that happen in the middle of the night. So, a little bit of time is going to save you a ton of time later. It’s just not going to feel like that in the beginning.
Rob: That’s the way to think about it. At a certain point, when we hit scale, and I believe it was post acquisitions, we had thousands of paying customers and I think, if we have the free plan, it was tens of thousands of people using it. This is Drip, of course.
We did talk about implementing end-to-end, front end snapshot testing in that sense, but it was only going to be for one or two flows. It was going to be the sign-up flow and something else critical, like sending a broadcast email because we knew that those two flows people use all the time, and if one of those failed, then we have a real problem.
Tracy: That’s a good point, actually. If you look at what are the critical flows are, when it comes to payments, or registration, or whatnot because when you’re launching new features later on, you want to make sure when you add those features, you can run those tests and make sure you didn’t inadvertently break those flaws.
Rob: Exactly and that’s the thing. For Chris, the original question asker, the thing to think about is how well do you know your co-founder? Does your co-founder tend to be extremely conservative? Does he or she come from a Fortune 500 company, or a bank, or NASA, or Lockheed, or somewhere where they had to have ridiculous test coverage that can never fail? Or have they worked a lot on startup environments? And what’s their personality like? Did they take it fast and lose? Did they hack stuff together? Their PHP hacker used to do it on the weekend and they never do the official stuff. They’re really tight knit unit testing ideas, or are they somewhere in the middle?
I think that almost counts for a lot and to be honest, I trusted my co-founder, Derek, a lot in the early days. I said, “Look, right unit test. Of course, we need them, we’re absolutely doing it,” but I let him go from there. I didn’t come in and say, “Oh, we should have this tested and that not tested.” I trusted his judgement that he’s conservative enough, that he was stressed that things are going to break about the same amount that I was. He wasn’t overly stressed nor too lax […] to cool with it. So that wound up being a pretty good relationship there.
Tracy: Cool. Should we move on to the next question?
Rob: Indeed.
Tracy: All right. This question comes from Tom, the founder of Tom’s Planner. He started working on this in 2007 and though the current design of the product itself dates back to that year, though it had a significant update years years ago, but starting to feel outdated again. So, he’s looking at doing another redesign.
He says, “Now, I have four designs to choose from. Each has their own strengths and weaknesses. I really like one of them. I decided to be a good idea to pull my most active users about it as well. That’s where the problem started. The users prefer another design than I do. Even worse, they scored the design I like the lowest. So, now what?”
He says, “Going with the majority would make sense but there’s a couple things to consider.” He really likes the other design. The design that the other users scored best, looks most like the current design that we have now and I’m guessing that’s part of the reason why it’s doing so well. People don’t like change. The design that he likes most has a timeless quality to it, which he believes, which is important to hand but the users probably don’t take that into account and the users are quite divided over it. Even though there’s a winner, no design had a bad finished. “Am I inclined to, despite the results of the poll, choose the design I like best and think this most future proof, but since it is the design users like least, I am still in doubt. Any advice?”
Rob: This is a tough situation you’ve gotten yourself into, Tom. I feel bad for you because I feel like asking users their opinion is pretty much not something that I would recommend overall. Tracy, you run a wedding marketplace, for wedding services. You had consumers like brides and grooms who are buying from service providers. Did you ever ask or poll your users for specific opinions like this?
Tracy: I did not for the site itself but there was an aspect of WeddingLovely where people could have their own wedding websites. I let users have the choice of emailing me and asking me for a custom design and that was a terrible, terrible thing to do. I end up ripping that out because I got overwhelmed to feedback and people were choosing and asking for things that I thought were bad design and didn’t reflect the brand. I end up actually removing that feature entirely.
So, I’m very strongly in the camp that I would prefer not to talk to my users about designs because, as Tom mentions, it can make things really complicated and I also worry about what would happen if you launch a design and it’s not the ones that someone wants. What would happen with the person who voted for the design? What would they feel? It’s a very sticky situation.
Ro: Yeah. People can be really opinionated about things that they’re not experts in. That’s an issue. Design is not something that we all have a training in. I don’t hire the person down the street to correct my back or to do surgery on my knee when I had knee surgery. I hire people with expertise. I don’t go down the street and hire a 15-year-old kid to write code for my website, although, he probably could. I hire people who have experience, and expertise, and training, and knowledge in the space. Design is the same thing.
Everybody has opinions but do they have taste? It’s an interesting thing and I don’t want to make it out like being snooty like, “Oh, I have taste because I only drink refined wines and these very pretentious single source origin coffees,” which my brother does and I say, “We’re going to go to the pretentious coffee place or go to the cheap one?” Of course, the pretentious coffee taste better but it’s $15 a cup.
I think if it’s all designers and you really want to get opinions and feedback, then do that. I think it’s more trouble than it’s worth, and I think it will create problems every time because what’s funny, as Tom said, that his users picked the one that’s most similar to what they already have because people don’t really like change and they don’t like using new software.
If you know that in 2007, 12 years ago, that you designed this thing, that design probably isn’t going to last in another 10 years. You want this one to at least another 5 or 10 years. If I had been in Tom shoes, I would not have done this. We would ask for opinions about, “Hey, we have some features. What do you think about this or what feature doesn’t this software do?” Those are interesting things because those are actual things that they’re doing in day-to-day business and they are experts on their own work flow and on their own needs for a product. But asking what color the button should be, or how a page should look, or showing three designs for a page, aside from just pure use ability things, like “Wow. I’m totally lost. I can navigate this,” that makes sense, but there are opinion on whether there should be a drop shadow or not, or a font. That’s why I hire experts or become an expert yourself, I guess.
Tracy: There is another piece of this puzzle that’s missing, which is that in a redesign, […] the user experience, not just the interface. When you’re asking people, it doesn’t really say about how we ask for feedback on the design and presuming it’s screenshots and that’s leaving out how the interaction actually is.
The users might be choosing something that looks like the old design because they don’t want the placement of buttons and how things work underneath the change. The thing that I struggle with new design is I’m trying to figure out how things are going to work and who might be scared about changing the system.
When one is doing a redesign, I think it’s important to include how things work and try to improve those flows about how someone uses the website, how someone signs up, or ask for payment information, whatnot. You don’t get feedback on those things when you’re sharing screenshots. So, that could be another thing for Tom to do, is do another round of feedback but not by users but go cray away of testing out the interactions about how things are working and see if his new design does better on that aspect. Does that make sense?
Rob: Yeah, it does. He did do screenshots. He included a link way at the bottom that has a link to the screenshots. One of them doesn’t work but the other one says he has all four designs and frankly, they’re all pretty similar. I actually don’t think it matters which one he goes with.
Tom, my advice would be don’t do this again because having trying to do it by democracy. If you have a product, you should have a pretty strong opinion and a vision for your product, I think. If you want to do a fun contest or a competition, that’s fine. But if really, it’s something as fundamental as the design of your product, that’s where you have to be.
You’re the founder, you’re in charge. You can certainly ask some opinions with people that you trust. You can get two or three designers together at your company. You can get people who have expertise to weigh in. When I was designing or having the TinySeed website designed, I asked a couple people that I know that are really good designers, that have a really good eye for fonts, and this and that, and I trust their opinions. But I didn’t go post it somewhere and ask for the opinions of everyone on my email list because I just don’t think that’s that productive.
Tracy: It’s just going to be a lot of noise and a lot of confusion, probably a lot of stress. It’s such a qualitative product. You don’t have any numbers to bring it back on to and that could be something. Also, when you’re choosing in a redesign, if you can do A/B testing of some sort, maybe on smaller elements, you’ll be able to say, “Okay, this one definitely works better.” More people are signing up or doing something that you want them to do because you can tie that to numbers but with just asking someone’s opinion about what looks better is not going to give that much useful feedback.
Rob: I hope that was helpful, Tom.
Tracy: Sorry, Tom.
Rob: Good luck. Our next question is a voicemail about which side to focus on when building a two-sided marketplace.
Chris: Hey, Mike and Rob. This is Chris Bowles from Kentucky. One of the […] for TinySeed, first batch. My question is relating to chicken or the egg with SaaS B2C/B2B. Got a startup concept that I’ll actually be providing free trial on the B2C side with a very small revenue figure to help support the B2B side.
Without going into a bunch of detail, basically I’m in stealth mode right now. How do you know whenever you recruit the majority of your revenue through the B2B side or you provide the trials to the B2B side versus beginning free trials on the B2C side? How do you know who to market to first and to who to set up on the website prior to launch to be sure everybody […] on […] day? Thanks for all you do. I’ve learned a lot. Have a good one.
Rob: Okay. It’s an interesting one. I think you’ve gone a little into the wood with the free trial and that kind of stuff. I just think about this as a two-sided marketplace, and there’s a business and a consumer side. My translation of his question is which side do I need to bring to the site first? You’ve built a two-sided marketplace?
Tracy: Yeah. The chicken and egg problem is tough because you need to have enough on both sides of the equation for your website to be useful for both. With WeddingLovely, it was a marketplace for wedding businesses and that was the primary focus. There was a consumer side where there’s a planning application. My recommendation is to focus on the businesses.
My personal experience with WeddingLovely is I actually the site very early on which is a few businesses because I needed to have something online for these businesses to say, “Okay. This is launched.” I’ve seen other people using it and I even told those businesses like, “Hey, this is something that’s going to be a slow growth thing.”
In the beginning we might not be able to send them a bunch of consumers, but I was live and they’re listing to the site for free. By focusing on the businesses, they actually help my marketing a ton because I was able to work directly with the people that were on the website with WeddingLovely. They had their own network, social media, blogs, and whatnot. So, they helped build up that consumer side of the business while I focus most of my effort and intention on the business side.
It was a […]. Market places take a long time to build up both sides but I’m a fan of working, I mean, businesses are also easier to work with, by far. I think there’s going to be a lot more benefit through focusing on the business side. What do you think?
Rob: I would focus on the business side first, in that case. I would basically have a landing page somewhere, or a social media account, an Instagram account, or something that is posting amazing stuff and trying to forget this consumer side. Some type of traction so that I don’t have to start from zero. Once I have 10, 20, 30 businesses lined up, I at least have an email list of a hundred people, or I have a thousand Instagram followers, or something there.
Typically, what I say when people ask about how to setup a market place is focus on one side first and in almost all cases, it’s pretty obvious which side you need. If you had a bunch of consumers with WeddingLovely, and you’re like, “All right. I have 5000 people who wants services,” and you have zero services, you have zero businesses, there’s no business there. So, you have to bring the businesses first.
The challenge is, of course, you have to bring the businesses to a place where you don’t have any consumer audience. You could then step back and say, “Well, should I start a blog, or a podcast, or an Instagram following, or an email list, or something that gets the brides- and grooms-to-be?” then from there, say, “Well now, I have this email list of 20,000. Now, I go recruit businesses?” That could be one way to do it. That’s another way to think about it. But you’re starting on a cold stop on both ends, right?
Tracy: Yeah. Chris mentioned that he was in stealth mode. I think that’s something that should depend on what he’s working on, but I feel it needs to be something that you have to get out of stealth mode so you can start recruiting people on either side of the audience.
Rob: Yeah, I would agree. Everytime I hear stealth mode, there’s certain yellow flags, red flags are probably stronger, but stealth mode is one here, “I want to raise money from you. Sign an NDA. I’m building a startup that targets every small business in the United States. It’s any business and there’s 60 million of them, that’s my target audience.” There’s just certain things that’s like, “Yeah. You’re making a basic mistake,” in almost every case.
Typically, the people who make stealth mode work are these really experienced founders. Ev Williams can do stealth mode. He’s done Blogger, and Twitter, and Medium, and on and on. He can do what he wants and break the rules. Steve Jobs can do stealth mode. There’s a handful of people that can do it, pull it off, and it works. But honestly, if it’s your first one and trying to figure stuff how, don’t do that. Just get out there. You need to start generating interest on both sides of this. I agree. I would start at looking at getting businesses on board and having conversations.
Here’s the thing I would do. Whatever it is, if I can bring you 500 customers a year or 10 inquiries a month, or whatever that number is, is this of interest to you and is this worth $99 a month for you to subscribe? That’s your customer development. You have to do it in theoretical because you don’t have that other side of it yet. If they say yes, then awesome. Get on the waiting list, there’s no commitment now, let me get your info, and then you go to the other side and you either start running ads, or you start SEO, or you start social, or you start whatever it is that’s going to bring that consumer side, and you start funneling them somewhere.
You don’t need to write a bunch of code to do this. You can funnel them to a blog, funnel them to a landing page, you can funnel them to a hacked together WordPress site that has a couple of listings that you literally put together by hand. I mean, all this stuff can be done with just hustle. You don’t need to go pay $50,000 for developers to go build anything. You’re just trying to test it out. You’re trying to push it forward a piece at a time.
Tracy: This is a great place to things that don’t scale. For those businesses, what can you do by hand for each of those businesses in the beginning just to start getting the ball rolling.
Rob: Indeed. Thanks for the question Chris. Hope that was helpful.
Next question is another voicemail. It’s about connecting with other founders to build relationships and he’s referring back to a comment I made a few episodes ago.
Michael: Hey Rob and Mike. This is Mike Whitbeck, one of the co-founders of UberWriter. We worked in the mortgage space and we built some income calculation software. We’re on our 5th year of business and I’ve listened to hundreds of your episodes. One of the co-founders, David Stamm, and myself have used a lot of your advice of the podcast to help reguide and redirect our business in very successful ways. Our website is www.uber-writer.com.
On episode 444, I believe you mentioned that you and your wife, for about the feelings of isolation, have other entrepreneur couples over maybe once a month or have dinner with somebody just to talk to people that you relate with. Though it’s probably a little bit weird and just trying to figure this out is, I know I’ve run in the past where you introduce yourself to another couple, just basically go out to dinner, a movie, or a common event with them, and maybe you just don’t kind of hit it off. I guess the awkward question is, when you meet up with these people, is it generally an expectation that you’re going to meet again or you just let the friendship go or not go where it goes? How do you handle that? Enjoyed the podcast. Please keep it up. Have a great one guys.
Rob: This is an interesting question. I think there’s a couple of things. One for me, when I was younger, I felt like I had the need to be best friends with people or not friends at all. It’s just a very binary thing. I’m talking like junior high and then high school. That’s how I was raised. That’s how my family did stuff. It wasn’t until probably after college where I realized, “Oh, having other friends who you just hang out with and aren’t necessarily your best friend or it’s not this binary thing, but you can hang out with them now and again, once a month, once every other month, you see them. It’s nice, but that’s it,” is a good thing. I think it’s a good thing for all of us to have larger networks than just one or two people. Not a requirement, but it gives me accessibility to more people to go see Avengers: Endgame when I need to and I’m not just relying on one or two people. That’s the first thing.
The second thing is when we invite people over, we literally just say, “Hey, we’re having a couple of people over that we know. We’re all startup founders and we’d love to have you over.” That’s the expectation. In addition, we tend to invite two couples or three couples over. That helps it not be awkward if, for some reason, there is one person in the group can be whatever. Talk too much, not talk enough, be a train wreck, whatever, and that won’t ruin the thing because you have six or eight people there. Whereas, when it’s just a double date, you really are reliant on the personalities of the folks around you, and that, of course, can be a wildcard.
So, there’s strength and numbers there and there’s really no expectations beyond that. We say, “Hey, we do this a few times a year and we have people over blah, blah, blah,” and that winds up being the situation. It worked out well for us. So far, we haven’t had any of those situations where it’s actually been bad or awkward. We haven’t become best friends with everyone, but that’s okay. That wasn’t the expectation up front anyway, neither from us nor the other side. It’s just a natural conversation about random stuff.
What’s been interesting is some of the funniest conversations have not been about our companies, have not been about our businesses. It’s been topics surrounding fact. Just that startup founders tend to be creative, driven, motivated, smart people, who are perpetually learning, and just being in a room with those kinds of people and asking what shows they’re watching, what kombucha you’re drinking, what’s the best coffee place you go to, what conferences you like right now, what books are you interested in, what podcasts do you listen to.
This stuff is all tangentially related to work but we’re not sitting there analyzing each other’s businesses, giving us advice on pay-per-click ads and positioning. It’s much more this almost social conversation. What I find is that when I’m talking to, again, interesting, driven, smart people who are shipping things, it just tends to be better conversation no matter what we’re talking about.
Tracy: This question really resonates with me. I don’t know if you had the same issue when you moved to Minneapolis. I’ve moved to Toronto about three years ago and I left all my old friends behind. When I moved here, I wanted to jump in and make friends that I think also do the same thing I do so we can have conversations. It’s been a hard slog. It’s really hard to make friends as an adult. Tying it to a business is even harder. So, I really like your suggestions and I think I learned something from this. I’m going to try to do a little bit more social stuff.
One thing I wanted to mention was, one of the best parts about just meeting up with people, not having a lot of expectations, and just hanging out, especially if you’re a founder. You’ll probably going to see them at the networking events in your city or around the world, or wherever you go, and just making those small connections. They’re not going to be best friends, like you said, but then making these small connections can be really fun because you’re going to see them later on. You’re in continually reinforces connections overtime and I think it’s really great to have these people.
For me in Toronto, I have people I see. Probably it’s just simply at events and they’ve been over at my house one or two times. It’s been really fun to start making those relationships and for a few people it has. Eventually, it’s going to move into, “Okay. Cool. Let’s talk business. Maybe I can tell you a problem I’m having. Maybe get some advice.” Just starting out and meeting people for the first time, don’t worry about talking business. Just see if they’re a good fit for you and not that everyone’s going to be.
Rob: I completely second the notion of how hard it is to make friends as adults and I don’t know that anyone ever told me that when I was growing up, but it just seems like you made friends in school, then you made friends in college. Shortly after college, if you’re still around those friends it was easy, but moving to a new place or relocating is hard.
I’m actually thankful because Sherry is pretty deliberate about wanting to find a community in various aspects of our lives. That has caused her to essentially just start making lists of people that we meet anywhere. We go to a meet-up, I did a little talk here locally a few weeks ago or any of the mirative startup events. Anybody we find that’s interesting, she’s like, “Get their names, get their email, and we’ll put them on this list.” We have this Google Doc of people now that is literally just a grab bag of some people we know relatively well and others we don’t, but we’re interested in getting together with them. We introduce them to one another often, which is cool. It’s not like our goal is to get everybody to network, but that at least there’s some value to everybody.
Tracy: Yeah. Think about talking to your 15-year-old self, being like, “When you’re an adult, you’re going to have spreadsheet of potential friends.”
Rob: And you’re going to have to invite them over for dinner. That’s just how it goes.
Tracy: I just have one more thing. Another thing when I moved to Toronto is that I insisted on working from a coworking space. That was also to get more business friends by working together and being around these people. There’s a lot of people at this coworking space after the last year, so have I grown into friends, we’re talking of business ethics because we’re there working together. I used to work at home in an office and this has been really great for me socially. It’s been really great for me careerwise, just to be around people while I’m working and then you have that little back-and-forth chit-chat. Then it grows into who am I going to invite over for dinner and doing dinner party or whatnot.
Another option that I usually recommend to a lot of people who are working solely from home is if there is a place so they can also try to make friends through coworking spaces, you might be able to build those relationships.
Rob: Literally, once a month, once every two months, it’s not that big of a burden. Frankly, you can couch it as, “Do you want to come over? We will literally order take out.” You really don’t have to cook for them. There isn’t an excuse. I’m talking to the listeners more than you Tracy.
There’s literally no excuse not to do this because when we brought this up before, I’ve had people say, “Wow. That sounds like a lot of work. I don’t think I have time for that.” We have three kids who go to three different schools. We homeschool one of them. Talk about not having time, my wife and I both work full time and do that. And yet we do this. It’s because we prioritize it. It’s not because it’s easy. Sometimes, we’ll do take out or we did potluck last time, where we provided the main thing that I grilled and people brought a salad, and this and that. It’s very little work for us.
The other thing is everybody brought their kids and they all played in our basement. Nobody needed to get sitters because that’s another hassle and expense. Frankly, it is finding sitters who are reliable and all that. There are ways to do this if it’s something that you’re motivated to do and that you think is valuable.
Tracy: Just like setting up a whole dinner party. Even just being proactive about inviting people to lunch. Maybe you said it personal goal of that twice a week, you invite a person to go on a lunch with you. Maybe you’re already at work, you don’t need to get a sitter for that, it’s a very low stress situation. That’s something my husband does and he does it way better than me. Every week, he has a different person he goes to lunch with. That’s how he creates and also build those connections.
Rob: Yep. So, thanks for the question. I hope that was some helpful food for that.
Thanks for listening to this week’s episode. Hope that was helpful to hear. Tracy and I talking through listener questions. If you have a question for us, you can call it into our voicemail number. It’s 888-801-9690. You can always email us at questions@startupsfortherestofus.com. We’ll talk to you soon. Thanks for listening.
Delightful time cohosting. Thanks for having me!
Thanks for answering the question on testing. Sounds like what we are doing is as you described Rob so it’s good that we are on the right path.