Episode 508 | Finding Marketing Channels, Seat-Limited Trials, Building a Brand, and More Listener Questions

Rob: In this week’s episode of Startups to the Rest of Us, I’m joined by Asia Orangio. She and I answer listener questions on finding marketing channels, seat-limited trials, building a brand, and a bunch of other topics. We had a great time doing it.
Before I dive into that, I want to read a snippet from an email from a long time listener, Josh. He said, “Hey Rob, congrats on the 500th episode. Truly an epic accomplishment. I want to say I enjoyed the new format. The recent two-part episode with you and Jordan was epic. It could just be recency bias, but I don’t recall an episode that went so far into the weeds of the later bits of company building that I’m so familiar with. I also enjoy the following episodes with founders, and the way you intro those and talk briefly about their history, so you can get to the meat so much faster. The one this week with Derrick Reimer did that really well. Your solo episode was great as well, it resonated with many thoughts I’ve been harboring for years.”
He wrote a very nice email that I’m summarizing. He ends with, “Feels like I can just rant with you and have a beer about topics like this, which would be great. What this all circles back to is that I want to commend you for your approach. As one of the listeners mentioned in the 500th episode, your authenticity is very much appreciated. Everything you do is thoughtful, pragmatic, and truly helpful to the community you and Mike have built. Here’s to 500 more.”
Thank you so much, Josh. It honestly means a ton and I really appreciate hearing that. I know that we have been getting a lot more letters, and comments, and thoughts from listeners about episode types, topics, and just different approaches. I find that the more I’m experimenting, the more that people are able to weigh in. Like the recent Twitter poll I did where I said, should we redesign the podcast logo? I believe it wound up being about 58% no and 42% yes. We’ll see here in the coming months if I get the itch to think about redesigning it.
With that, let’s dive into our listener questions today. Asia Orangio, if you’re not familiar with her, she is Asia Matos on Twitter. She is the founder and CEO of demandmaven.io, where she helps SaaS founders find their first 100 customers, first 10,000 MRR, or first10,000MRR,orfirst100,000 MRR, with the confidence and clarity of a custom growth strategy and roadmap, and she helps with implementation, too.
I have a ton of respect for Asia. She’s doing great work. She does some work with TinySeed founders, she does work with a lot of founders in the MicroConf space, and she just has a killer marketing instinct. She knows funnels, she knows how to get in, do jobs to be done at interviews, execute on marketing channels to find one that works, start to scale it up, and work with founders to do that.
Asia has a wealth of knowledge. Actually, if you haven’t been listening to the In-demand Podcast, she started it just a few months ago. It’s just her on the mic, sharing her thoughts and her wisdom. I highly recommend it. It’s called In-demand. And with that, let’s dig into our listener questions on finding marketing channels, seat-limited trials, building a brand, and a couple of other topics. I hope you enjoy it.
Asia Orangio, thank you so much for joining me on the show.

Asia: Thank you so much for having me. I always love just working with you guys in general and super excited to answer some questions.

Rob: Me too. I am stoked, and given your experience, we have some good questions about finding the right channels, about branding, and about all that kind of stuff. I’m stoked to dive in. Per our typical listener question format, voicemails go to the top of the stack. Our first voicemail is from Mike Lawler.
Mike: Hey Rob, I’m working on a modified first step of your stairstep approach. My app migrates subscriptions from whatever recurring billing software you’re using, charge fees, or Recurly, et cetera to Stripe Billing. The one-time fee that I’m considering eventually morphing into a productized service. I believe in the demand for the product. I’ve been contracted to this exact thing two different times and then contracted another time to migrate and app onto Stripe Billing. I’ve talked to some of my fellow engineering managers that I know and they’ve done something similar or have it on the roadmap.
What I’m trying to figure out is what would be the most effective way and who would be the most effective group to market my product to? I think that there’s a strong argument to market to both developers so that they can educate the CEOs if that ends up on their roadmap, and then also to the CEOs and founders of different SaaS companies. I’m unsure what would be the best channel to do this, LinkedIn, Twitter, forums, et cetera. I don’t think the SEO and SEM would be particularly effective because I’m not sure how many decision-makers are searching for things like switching from Zaura to Stripe Billing, or whatever it may be. Any suggestions you have would be awesome. Thanks so much.

Asia: I love this question because my honest first thought was why not SEO and SEM? Purely because, well, a couple of things to be thinking about from a more strategic perspective, and then what I would actually do, which is I think that from a questions perspective, to be thinking about and mulling over is, who is the person who is ultimately going to live a better life because the product or the thing, and the service or whatever it is it’s solving that problem for, is that ultimately the CEO, or is that ultimately the developer?
I think that something to explore, but my guess is that, while it might not be the fastest channel in the world, if this is enough of a pain or problem, someone is probably searching it somewhere. I think the SEO and SEM route is actually what I would start with. I would do the research, of course, and that wouldn’t be necessarily a thing. I would just double down immediately.
I think you’d have to use a tool like Moz or Ahrefs to come see are people actually searching this. Based on the result that Google is serving up, in theory, if the search results are relevant to what you guys ultimately do, then that actually might be a very valid channel. That was my first impression. I’m curious though, Rob, what your thoughts were.

Rob: I was thinking that SEO might be the longer-term play, so it’s something I would get in quick, but I think to run quickly for that, I would start looking at Quora and Stack Overflow. My gut is that, as you said, founders and CEOs, if it’s a 100- or 200-person company probably don’t care, but if it’s a founder CEO of a five-person startup, they’re still involved in the Stripe Billing or the charge fee migrations.
That’s one place, but I really think that in general, it’ll be the developer. It will be some kind of developer who winds up doing this. When they go to Google to search, migrate from any of these places to Stripe, Quora should rank pretty high.
Shouldn’t there be (I’m guessing) a question like, how do I move from Chargebee to Stripe Billing? I would Google that now and see what’s in the top 10, or any of those places where you can contribute. Any of those are kind of user-contributable forums or whatever, Stack Overflow is the other one because (again) developers are going to use that.
I think if you wrote an article about that today in a brand new blog, I don’t think it’s going to rank immediately. That’s where I like Quora, Stack Overflow, even LinkedIn, Facebook groups, Twitter. Twitter is not going to come up every day, but having a search for some type of monitor on this, sure, chime in on those conversations, maybe once a week you wind up with a customer, once a month. I don’t think that’s going to be some massive influx, but I do think that you have a bit of learning to do right now. You want to talk to as many people as you can and people with the burning pain point are just so much more willing to talk to you. That’s what I love about it
To your point, I love the idea. I’ve always loved the comparison, SEO approach, where you say, it’s in the old days, 10 years ago, it was like, here is Drip versus all of the other email providers. It was a big grid, a big matrix. Well, now, it’s Drip versus MailChimp, Drip versus AWeber, each of these individual pages. You do a bunch of long-form content, such that when someone says, comparing Drip versus MailChimp, either your page or MailChimp, or maybe Quora, I bet one of those three ranks at the top for that question. I feel like this could be a little similar.
My concern is, again, if I didn’t have a blog with any type of domain authority and I wrote 10 blog posts today, or 10 essays or articles, do you think those would rank anytime soon or do you think you’d have to build up that domain’s authority first?

Asia: No, it would definitely take some time. I’m actually kind of curious if SEM would be something that would be a little of a faster route, even if it’s not the most infinitely scalable channel today, just depending on, of course, the pricing model that you have, but SEM could actually be a way that you evaluate just the quality of some of those searches, if of course there’s enough traffic volume in general for that. That’s definitely what I would use to test ideas and also just to test the funnel overall, in terms of who is actually searching this and who is actually coming to the marketing side and converting, signing up, or asking questions. I completely agree with going wherever people are talking about this problem and this pain.
It sounds like it’s a very common behavior, which makes me think it’s something that people are talking about in some kind of capacity somewhere. Like what you’re saying, Rob, I would go there and join that conversation if I can. I didn’t even think about Stack Exchange, but yes, that would absolutely be another place or another channel. This may even be a stretch, but Quora could also be a place where you test the advertising platform as well. Quora ads also exist, and if I’m not mistaken, depending on the query, you can get some pretty qualified traffic industry engagement overall. It’s definitely a test channel, definitely something to just try with a limited budget, if you have an advertising budget in any kind of way.
I would be looking at what are the most intent-driven channels that you can identify, related to that behavior, and related to that person. I would put SEM in there, Google ads. I would put Quora in there, the same thing for Stack Exchange where people are intentionally looking for a way to solve a problem.

Rob: I like that you’ve just defined that because I think some folks might not know what intent-driven ads versus (I guess) demographically-based. That’s like the Facebook ads, where this person likes Dungeons and Dragons and they live in Minneapolis, versus this person just said, how can I migrate to Stripe? That’s intent versus just who they are. The platforms you named—Google and Quora—would be really good in 10 months.
You threw out a term, SEM, which you and I both know that means, but I’m imagining someone maybe listening to it, wondering how is that different than SEO? SEM, Search Engine Marketing, is just kind of a synonym for buying ads on search engines. It’s usually pay-per-click ads on Google is how I think of it, but of course, it could be. There is SEM in Amazon.
You can buy ads if you have a book or product up on Amazon and you see the sponsored ranking there. Obviously, you can buy on Bing, YouTube, Google, and Yahoo, I guess anymore, I don’t even know at this point.
I also really like the question that you asked at the start which was, who will live a better life because of your service or product? That’s such a good thing to be thinking about as you get out and try to launch this. Thanks, Mike, for the question. I hope that was helpful. Our next question is from Cole Huey.
Cole: Hey Rob, Cole in Minneapolis here. I’m working on an app that facilitates HR employee onboarding processes. The set-up takes a medium amount of effort. It’s not integral to the business but definitely takes some intentionality to set up. I had the idea of allowing them to create an account for free as a single user and take as much time as they want to set it up and have them pay once they start adding other users. Because of the nature of the app, they can’t get value out of it on their own, so I think it prevents any way to abuse it. Any pitfalls or drawbacks that I’m not seeing in this approach? Thanks.

Rob: Interesting question. Asia, do you have thoughts on this?

Asia: I have so many follow-up questions.

Rob: Let’s do it. We’ll just go. I’ll just answer your questions. We’ll make it up as we go along.

Asia: Okay. This is a tough one because, for me, I think so much of how you think about the onboarding process in general and then also how much do you give away and how much time do you give someone to start making a decision. I think so much of it does depend on just your overall positioning in the market from a product perspective. How white glove is your approach, for example, from a product perspective? Just how much friction is there naturally before time-to-value is ultimately met?
Those are all things that we don’t necessarily have all the information on, but I would say if there’s a lot more (for lack of a better word) friction to get to aha moment and the product, if it takes just more time, in general, to configure things, to get things set up, part of me wonders is ultimately possible to speed that journey up? Without forsaking, of course, the overall customer experience, and also just getting to that time to aha moment.
I will say that no time limit depending on, just again, that positioning in the product space and then how complex the product is. On the one hand, I think that can actually be incredibly beneficial, but I also think it just ultimately depends on the user at the end of the day. It’s unclear to me at least who exactly we’re selling to, but I’m thinking, if it’s getting sold to an HR manager, that person is in a million different directions. With a no time limit kind of scenario, unless you just had some really intentional onboarding, whether it’s a white-glove approach or a fully self-serve kind of scenario, I think that you might end up getting forgotten. That’s what would concern me.
Maybe in the no time limit scenario, I don’t know. I could see pluses and minuses for both. I would be much more concerned about just the HR person or whoever is ultimately using the product just completely getting distracted at the end of the day.

Rob: That was my thought when I initially saw this or started thinking through it. Without some kind of time pressure, some type of demo where they either see you face-to-face, or they’re on a call, they see the product working, then you follow-up with them, and there’s some type of personal relationship, just not sure how an HR product works. Again, I’m under the same assumption that a busy HR professional is running this and that they’re the ones that would be purchasing.
I don’t see drawbacks to giving them a free single-user trial that they can’t do anything with, but I do think that personally upfront, it would be demo only because the learnings you’re going to get from doing demos are going to show you the pitfalls of the product, the questions they ask. You’re going to learn 10 times more than you will from someone just kind of tooling around in the app on their own and then bailing, which is what most people will do. That’s the first thing,
I don’t know that I would keep demo-only forever, but selling it to HR like this, I would price it such that you can because my guess is it will be high-touch sales. You’re trying to build a 20 a month HR product, selling to orgs is, how do I say, unless it’s20amonthHRproduct,sellingtoorgsis,howdoIsay,unlessit′s10 per seat or something, per employee that’s onboarded, permanently which doesn’t make a ton of sense, you need to have a high ticket price. I think you need to justify the demo only.
The time pressure thing is a little different. This is not going to be a self-service app. I don’t know of any HR apps like this that are just sign it and forget it. People sign up, they onboard, and it happens. It sounds like we’re in agreement, do you have other thoughts on it?

Asia: I completely agree. I think the only other thing I thought of as you’re kind of chatting about, who you’re ultimately selling to in the HR world at least. I’m just reminded of all the most popular HR platforms in general. What are the other SaaS tools an HR person might actually be using (like on any given day) today? I’m thinking about the experience that they have whenever they sign up for a product. Usually, they’re talking to someone at some point.
I just think it’s so rare to let an HR person, a professional, go willy-nilly into a product. I think if anything, in many ways, your experience will be compared to other product experiences, too. If a lot of other product experiences in this HR space is very much that personal touch, white-glove approach, then in a way, I would say, you’re literally competing with those experiences, but there might actually already be a standard that a demo can ultimately help you meet. Just from creating that personal touchpoint, but yes, I totally agree.

Rob: That’s one of the advantages you have as a founder, is in the early days and even as you go on, when you get on a call, it’s like, I’m the founder of this. I’m the lead developer and I’m going to make it great for you. There’s a little connection there. Now, that can scare some people off, so you’re not going to get Target or Best Buy to sign up with you the first day, but do you get a 5% or 10% percent target to be willing to invest in your solution? It’s possible. Thank you for the question. I hope that was helpful.
Our next question is about branding, it’s from Robert Brandl, and he’s from websitetooltester.com. He says, “Hello, Startups for the Rest of Us. As a longtime listener, I have a question for the show. I have become pretty decent at SEO and content marketing, but I was wondering if I should start investing in brand building at some point. I have a feeling this could accelerate our growth further.” Then he asks, “Can you maybe share a bit of the process of building the Drip brand or any other brands you’ve been involved with? Did you work with an agency? What were your goals and how did you measure them? Many thanks. Robert.”
Again, websitetooltester.com. What do you think, Asia?

Asia: I also love this because maybe it’s splitting hairs, just a tiny bit. I’m super curious to hear what you think also, Rob. There’s brand and then there’s branding. Branding is very much the colors and the fonts, and typefaces, and just things that you would leverage visually to represent your brand. Then there’s building a brand. I will say I am not a brand expert, but from the brand experts that I do know, many of them would say that brand is so much beyond just the colors, and the fonts, and logos, and things that you have in the graphics that you’re using, so much of it has to do with the overall culture of your business.
Culture (I think) is a word that can get sliced and diced in a million different ways, especially today. It might actually be very overused, but ultimately the core values of a particular business. Ultimately, when you think about building a brand, those core values are experienced by your customers, by your users, and people who look to your brand for guidance, wherever it is that you’re an expert in from an industry perspective, and then even beyond to where you get to the very highbrow Apple and Steve Jobs-level brand.
I think from building a brand perspective, I think what could be a different way to think about it would be, there’s a building that brand in that capacity, and then there’s also either generating more word of mouth from a channel perspective. I’d be curious if maybe how we think about and how we realize brand is really just looking to expand on the word-of-mouth piece as an extra channel to continue to just double down on, and what can we do around word-of-mouth to expand that, or is it literally, let’s actually build a brand, something that means something to someone. I would say that building a brand from a process perspective is much harder because it is so long-term, at least in my highbrow brand definition.

Rob: I like the idea of them building a brand. I think it will take them a while and I do think it’s a gamble. When I look at their site, they basically review website builders, ecommerce platforms, and hosting platforms. I’m sure they make buckets of money on affiliate links. It’s a nice site. It’s not the typical crappy affiliate referral set-up. It almost reminds me, given the quality of the content they have here (and I’m guessing their organic rankings, I’m guessing they’re just getting most of it from organic search), if I’m going to build a long-term business, it scares me. It concerns me that if no one ‘s typing my URL into the browser, then I am always beholden to Google.
The example I think of is similar to this if I were in his shoes, wanted to expand, and wanted to (a) diversify, but (b) get more traffic, I would personally look at Wirecutter. Wirecutter is just reviews and there were a bunch of reviews of all types of electronic stuff before Wirecutter. Wirecutter really just makes their money on a bunch of affiliate links, some […] ads and stuff now, too. But they just built a really high-quality thing. I will type in wirecutter.com and then I will search for their best earbuds, Bluetooth earbuds or whatever.
Why do I do that? Because somehow, they built a brand, and the way I heard about it was people mentioning it on podcasts, or linking it to an email newsletter, or something in the ether just started Wirecutter was a thing.
I don’t think that was by accident. I don’t think Wirecutter woke up one morning and is like, oh, everybody loves us. I think they had to pick some pretty deliberate steps to do that. If I was in Robert’s shoes, I would: (a) be looking at what did Wirecutter do, try to watch interviews with their folks and figure out if they had a plan, how did they execute on it, and (b) when I think about a brand like this, I want the founder to be quoted in all the articles that are on Forbes entrepreneur magazine, even trying to get on web shows and podcasts to get quotes, snippets, and press releases like an expert. It’s like, Robert so and so, the founder of WebsiteToolTester says blah, blah, blah, here’s our quote about this. You’re almost trying to become an expert, such that your site gleans with some of your expertise. I think that’s a first thought, and now I’m just brainstorming ways to try to build a brand.
The second one is, you have a bunch of written content, have you thought of starting, since we’re like a video show or a video review show of these things, is there anyone doing that and is that the next level here, or is it a podcast? I have to guess there’s a Wirecutter podcast. I’ve never looked, but given how strong their brand is, I would assume that there is.
I would think about, are there other media ways to go whether it’s starting that YouTube channel if you don’t already have it, is there a podcast. How do you elevate yourself above the other 50 website builder ecommerce and hosting review sites that are really just affiliate links, and they’re ranking the best one, are the ones that pay the most money at the top? How do you differentiate yourself from that? From there I think it’s going beyond just the written content and really thinking about what people resonate with and what other examples have come before me.
I think I’ll finish with this. When I think of a brand, I do like your differentiation, branding versus brand. I think branding is colors, logo, visual, this and that. I’ve read this somewhere, but brand is not what you do, it’s who you are. Brand is not how you see your company, it’s how your customers see it, or your prospects, or your visitors. It’s how they see it or hear about it.
When I say Wirecutter, if other people have heard of the site, they say, oh, that’s that reputable site that reviews these things and I trust their recommendations. Somehow, they built up that brand, it’s how we see them. Those are my thoughts when I heard it. I’m curious if you have other thoughts given our back and forth.

Asia: Actually, really a question for you, in your experience, how would you recommend someone build a brand from a personal brand and separating that. Or maybe it is just the same as the actual business brand, but how do you see building that personal brand versus the business brand, or do you find it’s very much the same?

Rob: I think you can do it either way. I’ve done both. Rob Walling started becoming a personal brand in the blogging space and then the podcasting space. Then we started MicroConf and MicroConf started becoming its own brand that was affiliated with Mike and I, the co-founders of MicroConf. Now, I was really all in. MicroConf was a thing we did on the side. Startups for the Rest of Us was a thing we did on the side, and really, I was still all in on the Rob Walling brand until I started Drip, and then I just got too busy.
What you’ll notice is, the Rob Walling brand these days is really tied heavily to the podcast, MicroConf, and TinySeed. Although I am the face of it, those brands are bigger than me. I’m not doing a bunch of personal. Go to robwalling.com and there hasn’t been a new essay in years, but you go to MicroConf, Startups for the Rest of Us, and TinySeed and there’s a bunch of new content coming out. Some of it’s from me and some of it’s from other people.
In his case, in WebsiteToolTester, unless Robert wants to become a personal brand himself (which he’s given no indication he has), although he can be the founder, the expert, and lend the insight, building a personal brand would involve him going out and maybe writing blog posts under his own name and starting a podcast where his brand is put ahead of WebsiteToolTester. But if you started the WebsiteToolTester podcast, and it’s just like, hey, I’m Robert, I’m the host of WebsiteToolTester, I’m the founder as well. Then he goes into it like, WebsiteToolTester gets the brand equity in that. In his case personally, again, unless he really wants to build a personal brand, I don’t think he needs to. I think he can build the brand without having to become the celebrity founder.
People can know who you are. Like Ruben Gamez with BidSketch and DocSketch, a lot of people, especially in our space, know who Ruben is, but he’s not some big personal brand, but DocSketch and BidSketch have momentum, and they really are these apps that have a lot of revenue, have customers and such. He’s been able to do that I think while being a little bit in the background.
If you look at Castos, a TinySeed batch one company, Craig Hewitt was the face of that brand. Then, he hired Matt Medeiros within the last couple of weeks from […], who is now the director of Podcaster Success. Matt is now going to start becoming more of that voice. I think the Castos brand is still very strong, and it wasn’t tied so closely to Craig that if Craig is only the co-host of the podcast, or takes a few weeks off of their podcast, or of blogging, or whatever. I don’t think the Castos brand suffers from that. I think that’s a really nice way to do it because it means that if you’re a 50- or 100-person company, Craig Hewitt doesn’t still have to be recording the podcast every week.

Asia: Thank you for that breakdown. I can hear that question in the back of some founder’s minds of, okay, but wait. Awesome, thank you.

Rob: Absolutely. Thanks Robert, I hope that thought process was helpful. Our next question is from Aton Efrati and he says, “Love, love, love the show, what you guys are building, and the message. Here’s my question, I got laid off because of Covid-19 and I’m looking to go back on my own. After more than five years of working for a venture capitalist, and then one of their high-growth portfolio companies, I know that I want to get involved in smaller profit-driven startups. I’m weighing a few different options of what my next steps could be.
I’ve got four kids at home, a supportive wife, and about six months of runaway. I’m trying to balance my confidence and enthusiasm with making smart decisions. I have a few options I want to layout for you and I’m curious to get your take.
Option one is high-risk, go out on my own which would start as contract work and evolve into a product type of service. I would continue to tinker on the side with other ideas and probably try to build a more substantial business in the next 1–2 years. This requires zero funding. Option number two, medium-risk. Join a fledgling startup that is inviting me to be the CEO to try to restart sales and marketing instead of closing down. They invested hundreds of thousands of dollars in angel money into building out technology, have dozens of paying customers, but it’s been several years and that company hasn’t taken off beyond break even. They have one full-time employee and two co-founders are still involved. They’d be paying me a meaningful profit sharing and equity.
Option number three is low-risk. Take a full-time job and tinker on the side with either freelance work, my own business idea, or someone else’s business idea. My market rate salary would put food on the table and then some, but I wouldn’t have much time to think or do anything outside of my full-time work. I appreciate any insight you have. Thanks in advance.”
Asia, what do you think? This is a fun one. This is an ‘it depends’ for sure, but let’s start with some thoughts.

Asia: From a decision-making framework perspective, if we really had to think about how we make decisions about just planning for our life and what’s important to us? Just looking at these options, it’s very clear that this person values entrepreneurship in some kind of way. This person wants to do something just on their own in some capacity. Going back to that statement of just becoming more independent. It’s very clear that this is a core value of this person.
From personal experience, I actually did number one. I lived option number one, which was going out on my own, starting as a contractor role, and then really building a service business over the next 1–2 years. I will say I did not quite go to the level of productized service, which I think is a step even further of the kinds of work that I do. But here’s the ‘gotcha.’ I don’t have children. I don’t have a mortgage. These are a few things about me making that choice and with the zero funding, I literally did it. I just started to do it.
The evaluation here is exactly right. It is absolutely high-risk. There is no guaranteed success for really any of these options. I’m very much someone who just doesn’t believe that job security is a thing that exists in the same way that it did 10 years ago or 20 years ago. Obviously, us even having this conversation, we’ve all got something entrepreneurial about us. I think in terms of thinking about how to make this decision, I think what I would do is a couple of things. I would try to really dig deep into what is it about being more independent and what is it about starting your own thing that gives this person the satisfaction and the fulfillment in life.
When we think about life just in general, what your goals are, and what you want to make sure that you accomplish before we exit the world. Not to make it morbid, but I think many of us, we’re motivated by something. There’s something about achieving that independence and achieving that level of independence that we’re obviously attracted to.
I think what I would maybe go back to the person asking the question with would just be, out of all the options, which one would you regret not doing? If you had to pick one, what would be the most regrettable experience out of all of them? Also out of all of these, what could you, in theory, do without? That’s how I would approach it.
I think in terms of just what I would do in this particular situation, given the context of just my family, my responsibilities, I hate to go in the middle of the road, but I actually think the medium-risk is probably the amount of risk that I would end up taking. Purely just based on my own personal values and the way that I think about what risk I would be comfortable taking.
I will say that it’s very clear that some amount of entrepreneurialism, or being a founder, or doing your own thing, or having a side hustle is very clearly important to this person. I would try to figure out what’s the minimum viable side hustle, or minimum viable foundership that this person can take and still be happy and feel fulfilled.

Rob: I love it. You kind of covered the bases, you covered regret minimization framework, although he didn’t say which of these would you regret not doing. That’s Jeff Bezos’ thing, regret minimization. Me personally even back in the day, I did go out on my own. I started as contract work and evolved into building and buying stuff on the side. I would have done option one and I had one child at the time, I did not have four, but there is some risk there and I think there always is.
The thing that I’ve always fallen back on is, depending on your skillset and your experience, unless there’s just a massive, massive recession, the odds of you being out of work are pretty low. You’ve worked for venture capitalists and then a high growth portfolio company. It sounds like you have some skills that are unique and will probably always be in demand. Especially now, we’ll be in demand remotely. I have to work for someone where I live.
To me, the low-risk of taking a job, I don’t know that I can ever recommend that for anybody in good conscience. Obviously, I had several salary jobs and I did it in the early days, but I think given that this is a turning point for you (it sounds like), I have a tough time imagining that you would want to take the low-risk. The fact that you were even evaluating the high and the medium, it implies that you probably (to me) shouldn’t take the low-risk.
The medium-risk one sounds interesting. That’s the one of joining a fledgling startup but it’s kind of failing in a sense and it’s flattened out. The fact that they’re only going to pay a meaningful profit sharing and equity, I don’t know if he’s getting a salary there or if he has to generate profit to do it. It’s hard to turn a company around. It can be really stressful. I guess if I knew more about the specifics of that, is it in my wheelhouse to do this, or is this a flyer where it’s like taking over this company just to see what I can do versus, I see the angle, I see the path on how to turn that around, that changes that calculus right there or some specifics there.
I did a turnaround with HitTail and I thought it was amazing. It was a great experience for me. I did it with a couple of other products before that, but it was a lot of work, and I didn’t know if it was going to work each time. There’s quite a bit of risk there.
I think something else to throw out is there’s a really good book recommended to me by Ruben Gamez, who I mentioned in an earlier episode. It’s Decisive: How to Make Better Choices in Life and Work. It’s by Chip and Dan Heath, who are known for their Made to Stick and their Switch books. There’s a framework in there about a four-step process designed to counteract the biases that most of us have, the emotional biases, and the pattern matching biases, just all these biases that are built into so much of our thinking.
I don’t know if a ton of you have time to read the entire book before doing this, but that’s something. I got it on Audible myself. I listen to it, take notes, and I refer back to it every now and again just to remind myself. If you’re going to make a hard decision, there are some frameworks to do it with.

Asia: Something that you said that triggered this memory that I had of when I started my business. It was really an opportunity cost question of what is the opportunity cost of option one versus option two. When I started DemandMaven, I was absolutely terrified, if I’m being honest. It was the most high-risk thing I probably could have done with a plan, but at the same exact time, no real proof that my service had service/market fit (if you will) but something that the CEO of my previous in-house—he was actually my boss from my previous in-house role—who really encouraged me to go out on my own and to do option one. Something that he said was, what is the opportunity cost of you not doing DemandMaven?
It really came down to, you could probably go take another in-house job, which no tea, no shade on that, but then there’s also, what would an MBA, Emory University—I’m in Atlanta; I don’t know any other university here in the state—cost? I was like oh my gosh, 100,000–100,000–120,000 maybe. He was like, okay great, so you’re going to go start your business for free and basically go get your MBA, learn way more about starting a business than most MBA grads probably today. Again, no tea, no shade to those who have MBAs.
The way that he framed that opportunity cost for me was also really what helped me make the decision. I did end up going for the high-risk option. Maybe like what Rob is saying, it’s very clear you have a high-risk tolerance. You’re evaluating these opportunities, but that also could be another way to think about, does the opportunity cost of what you’re leaving on the table.

Rob: I love it. Asia, thank you so much for joining me on the show today. Folks want to keep up with you, you are @AsiaMatos on Twitter, and of course demandmaven.io if they want to check out all the work you do in helping SaaS founders reach their growth milestones. Thanks again for hanging out with me.

Asia: Thank you so much. This was great.

Rob: Thanks again to Asia for joining me today. If you love this episode, I would super appreciate a five-star rating in whatever device you use, whatever app you use to listen to podcasts. I really appreciate it even if you can’t write a full comment. Getting some type of review helps me keep going and helps us keep pushing forward with the show. Thanks for listening. I’ll talk to you next Tuesday morning.