Episode 765 | TinySeed Tales s4e9: Making the hardest decision
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Welcome to the season finale of season four of Tiny Seed Tales. This is episode nine, where we hear how it all turns out for Colleen and Hello Query.

Before we get into this episode, if you're a founder who's interested in the right amount of funding without the unicorn or bust pressure to scale your SaaS to a billion, you're probably a good fit for TinySeed. Applications just closed for our spring 2025 batch, but you can get more details about our world-class SaaS accelerator at tinyseed.com slash program and get onto our mailing list to be notified when our applications open in the fall. And with that, let's dive into the episode.

I don't want to have a five-year side project. Like this is so important to me. I have so many friends and good for them that works with their life. I have a, actually, you know what? I have a five-year side project that makes $2,000 a month, right? And it hasn't grown and it just sits there. I don't want another one of those. Like I want to outpace success.

Welcome back to Tiny Seed Tales, a series where I follow a founder through the roller coaster of building their startup. I'm your host, Rob Walling, a serial entrepreneur and co-founder of Tiny Seed, the first startup accelerator designed for bootstrappers.

For the past two years, we've been following Colleen's journey building Hello Query. When we started these conversations, we hoped to document the path to success. Instead, we captured something equally valuable, the real, raw experience of trying to get a business off the ground.

While most startup stories end quietly behind closed doors, in this final episode, Colleen gives us a candid look at one of the hardest decisions a founder can make and gives us a hint about what she's working on next. Well, Rob, the good news is I have tripled my MRR since we last spoke. And if I recall, it was like 100, 150 a month. And so you're at 540 or something.

180. So although triple your MRR sounds really amazing, $540 does not a business make. So, you know, it's been a lot of thought about what to do with this. And every single one of those three sales, so that's three new customers since we last spoke, and we last spoke a couple months ago.

Every single one was like horrendously painful. I mean, it was follow up and follow up and follow up and onboarding calls and back and forth. And I just don't see a repeatable path to getting new customers. That is sadly the truth that people, I had more people that said they were interested. Like I said, three converted of that initial list.

But every single person finding them has been just like a needle in a haystack. And I want to point out that that doesn't mean it's not a viable business, but it does conflict with the fact that we're recording this in January of 2025. And last time we spoke, which I think was October or maybe November of 24, you said, I run out of runway by the end of December 2024. So if you were in the position you are now at 540 MRR,

a year ago, two years ago, where you still had all this runway, I would say, well, you're onto something. Keep pulling this thread, you know? And if you're like, I still have 12 months of, of runway from tiny seed money or what have you consulting, I, and I have the motivation. I'm going to keep going, but you have given this now. I mean, we started recording this podcast two years ago, almost to the day, uh,

And you were working on it for six, 12 months before that. So are you, is that right? Are you almost three years into this? So I appreciate that sentiment, but I would like to point out that I completely started over a year ago. So we're talking like different business, different tech stack. So when I look at Hello Query specifically, it's really like 10 to 12 months old. Right.

And so with that in mind, we could say, well, it's only a 10 month old business. You're already a 500 MRR and you have a thread that's being pulled and some people are jumping on it, even though it's a pain to find them. So does that mean you should keep doing it?

Or is it I'm out of money and I got to be done? So that's the hard part with these kind of small businesses is making that decision. One thing that is really important to me is I don't want to have a five-year side project. Like this is so important to me. I have so many friends and good for them that works with their life. I have actually, you know what? I have a five-year side project that makes $2,000 a month. Right?

Right. And it hasn't grown and it just sits there. I don't want another one of those. Like I want to outpaced success. That's what I'm going for. And I think although Hello Query itself is only about a year old, this idea that

Because the previous business was a different iteration on this idea. This idea is three years old. And I am just not seeing the traction for the amount of marketing effort and sales effort and cold outbound I have been doing. I am just not seeing the traction I think I should be seeing.

if I was actually building something people want at the right time. And I think timing is important here too. We can get into why this business hasn't worked, but I think timing is a big part of it. So why didn't it work? That's a big question. And, you know, even making the decision to shut it down or keep going, because even you asked me this a couple months ago and we had scheduled this podcast and I asked you to push it out. Do you remember? Because I was like, I'm not ready. Like, I'm not ready to make that decision yet.

And do you watch Ted Lasso, Rob? It's the hope that kills you, man. Like every month, like starting in November, I was like, I'm going to shut it down at the end of November. And then I'd get a new customer. December, I'm going to shut it down. Got a new customer. So it's just like, it's the hope that kills you. Ask anyone who started a business and eventually had to close up shop and they'll tell you it's hard.

You put so much time, money, and effort into making something work that walking away is a really difficult decision to make. It was such a hard decision to make. But I think when I look at the opportunity cost of continuing this, one customer a month, I mean, that's not going to be outpaced returns. That's a never-ending slog. And...

And that's kind of I've been doing that for three years. That's what I have been doing. So when I think about shutting it down, I think part of it is just my own like exhaustion with this idea. And you know, part of it is all the things that happened to get me to this point. Why it didn't work is a different question. And I have been thinking about that a lot. I often get asked, how do I know when to quit? And the answer is,

I don't know, but I have guidelines is really my answer. And part of my answer that I give is, are you just done with the business? Are you just exhausted? Are you, you don't have any new ideas. You kind of don't care about it anymore. There's no track. And you're just like,

I don't want to keep doing this. That's one factor. There's a bunch of other factors. How much traction are you getting? What are your mastermind, your co-founder, your spouse, your coach, you know, whatever, what are they saying? How long have you been doing it? Like, do you normally stick with things longer than you should? Or do you normally quit things too early? What's your personal band? There's a bunch of factors. But to hear you say, I'm kind of

It's felt like a never ending slog and it's been that for a year or two, three years. It's like, okay, I haven't heard you put it in those terms before, but that tells me you are kind of like quote unquote done, you know? Yeah. What is so hard about this? It almost feels like it might be starting to work and you always worry, right? You always worry. You're like, am I just one quarter away? I had three cold inbound this month.

I've had zero cold inbound for like six months and three people. One guy came through intercom and actually is paying me now. I'm like, oh my gosh. Yeah. Is it working? I don't know. It's so hard because if I, if I knew if I had a crystal ball and I was like, I'm one quarter turn away, like I'm on the right path, but I'm too early. I would slog along, man. I'm great at slogging. Like I can slog forever. What is so hard about this decision is that

it actually might kind of sort of be working, but it's working at this like glacial pace. But you have to hold that in comparison to starting something new, where to start something new would take me another year, right? You have to build product, you have to build all these marketing systems, you have to build, you know, there's so much other stuff around a business. So this is why this was such a hard decision is because I have come so far, but also like sunk cost fallacy, like,

I can make a lot of more money doing other things. And that's become so obvious to me recently that it's like, do I really want to continue to pour my heart and soul and my time into this thing when people kind of sort of seem interested? Mm-hmm.

If you recall from our earlier episodes, Colleen and her co-founder split. I wondered how much she thought that impacted the success or failure of the business. ♪

He was a database expert. And sometimes I wonder if he was still working with me, we would have his kind of like database clout to be like, he said it's safe and everyone trusts him when it comes to databases. I think that was huge. I think he was building the tech. And so when he left, we literally lost everything.

anything he had created. Like I was, I wasn't, I was completely starting over from scratch. I didn't have a half build application. I didn't have a design. Like I was just starting over completely from scratch. So honestly, I think it was a huge, huge blow. And, um, Hello Query is my thing. And I take responsibility for like how it hasn't worked out. I don't want to place blame on

But I do think it is a big reason. Like, it's hard not to think what if, like, what if he had stuck it out? Could we have made this work together? I still kind of think we could have, which is kind of sad. But unfortunately, it didn't go that way. And then you told me offline, you use this phrase, nerd famous, in quotes, as a potential contributing factor to, you know, the business not working. Describe what you mean by that term.

This is something actually you speak about frequently, but both my co-founder and I were very well known in our respective communities. We both spoke at conferences. We had a podcast. People loved us. And I think that brought us false positive signals because the reason after he quit, the reason I kept going with this idea is because it

It felt like we had all of these people who had said they were really interested. But looking back at those conversations, I'm not saying those people weren't interested casually, but I think that was more they just kind of wanted to be part of something, which is awesome and exciting. And I super appreciate their support. But that doesn't help us like build a product business. Look at his success in courses.

directly ties to his popularity in his community, right? Like if you're popular in your community, you do courses, you do coaching, right? Like that's how you capitalize on popularity. And we were trying to build a SaaS and popularity doesn't matter when you build a SaaS. Ta-da, build your network, not your audience if you're gonna build a SaaS. It's like, oh, like someone has said this before. I've never heard this before, yeah. I think...

I continued down this path because I thought I had a list of 20 people ready to buy. Literally in close, I have this list of 20 people that says ready to buy. Do you know how many of those people actually bought?

One. One. Five percent close rate on your ready to buy list. Right. And I mean, these are people I think what kind of amazes me about this whole thing is these people get on a call with me and I've done so many of these calls now. I feel like I'm pretty good at filtering through BS, like why someone wouldn't actually buy the thing. And I mean, like I just get ghosted hard. They get on a freaking call with me and then they ghost me. And so I

You know, it's the curse of the audience, but I feel like it's a double edged sword because you wouldn't have any initial interest if we didn't have those audiences. So it's hard to know. But I do think that's part of the reason I when Aaron quit. Part of the reason I kept with this idea, even though this was not my idea and I'm not a database expert, was because I thought, oh, I got that list of 20 people that are ready to buy. So that was really where it kind of got me.

Given everything that happened, I couldn't help but wonder what kind of regrets Colleen had about Hello Query. I guess I have regrets about the way I ran the business. I don't have regrets about doing the business. I mean, I quit a job, like a really good job, Rob, to do this business. It was a really good job. Oops. To do this. I mean, I regret how things worked out with my co-founder.

I wish we had both been honest about what we wanted earlier. And that is a, you know, that's a lesson. My next business, I want a co-founder because I don't really like doing it alone. I'm super lonely. So that's a lesson I'll take with me. I'll be like, you know, Aaron and I made this mistake. I think we would both agree. We made a mistake by kind of getting caught up in all the things.

and not taking a step back and being like, what do we each need? And what do we each want? So I've learned a lot about like what I want in a future co-founder. I regret we didn't handle our issues earlier. But you know, I made some

I made some really big decisions that have put me in this position. Like a big one is you might remember I had that like quarter million dollar contract when we joined Tiny Seed, which is probably why we got into Tiny Seed. But anyway, and I killed that a year in. You remember, we talked about it, which seemed like I don't regret that at all. Because the whole point of going through Tiny Seed was to put ourselves in a position to go big or go home. It wasn't to ride this

you know, kind of comfortable productized consulting situation. So I don't regret that. So I don't have a lot of regrets. Just a few. That's good. I think if you build a business or do any type of risky effort that doesn't work out, you're probably always going to have some regrets. And I think it's important to not think that just because it didn't work, that you made the wrong decision. The outcome is actually separate.

from the inputs, right? Yes. And there's this great book by the winningest football coach of all time, Bill Walsh. And the title of the book is The Score Takes Care of Itself. And throughout the book, he says things like, and then I'd win a Super Bowl. And everyone's like, you're going to win next year. And he was like, good God, this is brutal. And he said, no matter what we did, no matter how hard we trained, we controlled what we could control.

And we let the score take care of itself. And some years, he said, we had an amazing team and I was still a great coach. And we had Montana and Rice and we would lose the Super Bowl. And then other years we would win it. And I controlled what I could control and let the score take care of itself. So I think separating inputs from outputs is something that I think is often a more healthy way to look at it.

I like to think like that. I like to think, I mean, to be clear, this totally sucks. Like, I don't want to sugarcoat that. But I do like to think about it like I went all in and...

Not only did I go all in, Rob, I'm now doing it publicly on your podcast. So that's fun for me. Only 10,000 of your closest friends. I know, only 10,000 of my closest friends. Sorry, tens of thousands. I misspoke there. Oh my goodness. So when Aaron quit, we had even talked about like pulling this podcast. Remember? We were like, should we just shut this down? And then we were like, no, we're going to ride it to the bitter end. We want to tell the real story. I'm happy I went all in on this. And...

You know, I think you're right. Like I controlled everything I could control. I did all the things, right? I did the marketing and the sales and the content and the following up and the freaking cold calling. Like I built the product, like I fixed the product. I controlled everything I could control for.

And, um, I can't control how many people sign up. I can't control my MRR. And that's a super bummer because I have worked so hard by myself toiling in my office. Um, and so it's a super bummer, but I, I ultimately can't control, control that. And all I can say is like, I think there has to be an aspect of luck, a small aspect of luck here. And I didn't get lucky, but maybe next time I will.

Probably heard me say, I feel like success is hard work, luck and skill in different components. And luck is a factor. It's not the only factor. And I don't even believe it's the biggest factor, but I do believe that it absolutely is. And I also think the hard work,

is something we all can control and put in the hours. There's a skill set that you develop over the years that I think develops even faster once you've been part of a successful venture. Once you've done it once, you kind of learn some things. It's not that you can then apply that to the next thing directly, but it does build that skill muscle up. And until you have that, it can be hard...

you can have a lot of hard work. And if you don't have any luck, and your skills are, you're developing them, but they're not quite at the level of, you know, someone who's done this two, three times, like it can be really hard to get past those uncertain days. The early days are so uncertain. Yeah. And I think, you know, you look back again, trying to figure out why it didn't work. And for me, it's like, did I not pivot enough? Did I pivot too many times? Like,

I thought I would be able to pivot myself to this working, right? I thought it was ship, modify, ship, modify. And as we talked about at the top of the hour, like if I'd started this two months ago, we'd be like, this is going great. So there's a lot of just a lot of sunk cost and emotion. You know, it's kind of a mess, this whole business. After months of going back and forth, Colleen had finally made her decision. I asked her what that felt like. On one hand, it's nice to have made the decision.

Because there were many, many times this year when I was thinking about it. Should I? Should I? Shouldn't I? Should I? Shouldn't I? Right. So it's nice to have decided. And I think that's important to move forward. I mean, it totally sucks. Like, like, it is awful. I feel awful. So I wanted this to work so badly. And so it not working is a big disappointment.

But I also know that I'll get to try again, right? Like I'll get to take all of these lessons I've learned and try again. And it's not like the end, it's not like I'm 65 and I'm like, oh, I don't have the energy. Like I'm good. I could do it again. And it's hard to connect the dots. You know, you can't connect the dots going forward. You can only connect them going backwards. But I did start this thing, you know, this SaaS marketing gym, which has been awesome. And I think, you know, it was funny because

I started SaaS Marketing Gym with Leanna Patch, who is a brilliant copywriter. And we made a lot of money in a very short period of time. Like, and I don't mean that to be like, oh, we're so great. I mean, compared to my SaaS, like comparing this coaching, like I was like, my SaaS has made $1,200 in the past year. This thing made $12,000 in four days. Like clearly this is not doing something right here. So there was a bit of that where it was like,

oh, maybe this isn't, you know, this thing that I don't love. It's not really a passion project for me. You know, maybe it is time to walk away. It's still hard, though. It's still hard, Rob. Like, it's still very hard. And that's the thing that I want to call out here is like, obviously, we're going to end this season on a high note or looking ahead, you know, at the future that you have as you ride off into the sunset.

But I don't think either of us want to sugarcoat how much of a bummer it is to have to shut down a business, you know, and to not succeed at what you've been trying to do for one, two, three years. But also...

I've heard some aspiring entrepreneurs, usually it's like a developer working a day job who's doing just fine, says, well, what if I start something and it doesn't work? What if I quit my day job and it doesn't work? And I often say, well, what is the worst case in that scenario? Do you probably get another job at the end, right? Or maybe you've learned enough that someone will acquihire you, or maybe you've learned enough that someone will just hire you because of the experience you have there. Or maybe you start your next thing because you met someone, you know, there's like all these things that can happen that...

that are positives coming out of a failure. So I want to call that out of, for you, six months ago, if we would have said, what's the worst that can happen? Or even let's go back three years ago when you quit your job. I would say, well, the worst that happens probably is you just get another job. But now you're at a place where that's not actually, you're not going back to get another job. You've done the SaaS marketing jam, which people, if they go to Google, type in SaaS marketing jam, they'll see you and Leanne's smiling face there.

So you have this new business already that you're excited about. I would venture to say that part of the reason that that's going to be a thing is because of the relationships, the audience, the network that you've cultivated over the past couple of years in building relationships.

And so I don't know, I like to think of each thing usually as if I'm going to fail at it, at least can it level me up along the way? Yeah. And before we joined TinySeed, we weren't really doing any marketing. I mean, I have leveled up from a marketing perspective so much. And that's going to be tremendously valuable, you know, with all the things I do next. Is there anything, as you think back, that you would have done differently before?

during this journey? Ooh, that's tough. So practically speaking, I don't think we executed fast enough that first year. And that's a very practical thing, but we didn't execute on the code front. We were building this list of people who wanted the thing and we didn't ship the thing fast enough. So I think shipping fast, I mean, that's what everyone says, but it's still true. Shipping faster, I would do differently.

You know, so much of this is kind of a, I don't wanna say a crapshoot, but like in the very beginning, right? You're just trying things to see if they work. I probably also would have started cold outreach a year earlier. Those two things together, I would have done. Usually when people ask me about regrets with things, I often say, I wish I would have done X sooner. That's usually- Always, right? It's like, no, now that I know this,

I either had, I didn't know about this approach or I didn't know that I should do that. Or I was too scared. There are some times where it's like, Rob, if you could do my whole career over, what would you do? I would have done video earlier. I didn't do video really until COVID, until 2020. I should have been doing video in 20, well, once I sold Drip 2016, you know? And I just was like, ooh, I don't know. It's a hassle. It's complicated. I'm not good on camera. Like all this stuff, I have this my own. And is it a regret or is it just a thing of like,

The lesson I learned is like, do more shit that scares you and try to educate yourself on things that you don't know about. What are your blind spots that you should be doing? So, yeah, I think for me, things, a lot of personnel, like a lot of co-founder stuff would have handled that faster earlier. I knew that was kind of a problem and I didn't push on it. And, and,

you know, for reasons. Would have done that faster, would have shipped faster, would have done cold outreach faster. Like it's so many things. Even on the tech side, you know, once I was doing all the tech myself, I found myself dragging my feet on,

it wasn't even really dragging my feet. I just feel like I still could have been faster. I still could have pushed a little bit harder. Like because of the security stuff, I was scared to launch embedding. Cause I was like, Oh, I was like, Oh, cause I'm really good at thinking of corner cases. But when you're just getting started, like corner cases, aren't your best friend. So just so much stuff. So I think, I think in general, that's, that's true, right? Do more things that scare you. When I've asked other founders, when they're after their business has shut down, you know, what are things that,

that you regret or that you would do differently. I've never once heard them say, I would have executed more. So we moved too fast. We shipped too many things too quickly. You know, we took too many risks. Yeah. Nah, it doesn't, you know, it doesn't happen. Not at least not in our world. So as, as we look ahead then to your next weeks, months, years, what is ahead for you? What are you excited about? What are you working on?

Well, I'm doing the SaaS marketing gym, which right now is kind of a founder coaching, but it's founder coaching and marketing. We just finished our first cohort. It's three month cohorts and it went really well. The people have great results. So it's amazing to help people and then have them have actual new customers because of the cold. We really focus or I really focus on the cold LinkedIn outbound and it's working. Like, I mean, it's working. So that's cool.

So I'm going to do that. But the nice thing is as Leanna and I are dialing that in, it doesn't take a ton of time. So I think I have to have some big thoughts about do I try to expand coaching into a community and become more of a content coach creator? Do I do another product business? And if so, what would that look like? How would I get into that? What can I take from what I learned about Hello Query and apply it to the next thing I do? Very nice. We'll call Leanne Schneider.

Thanks for sharing the real story. I just really appreciate you coming on here for the past two years and sharing that, you know, again, the kind of the authentic journey and not sugarcoating it. And I think it will make a good story for people who have also shared

to have success and who have maybe had a failure or shut down to hear you go through it and be like, yeah, this is a normalized thing. We've all done this, frankly. Almost all of anybody who has had some success has achieved this. Or anyone who has had some success has probably had an effort that no matter their best efforts, they've controlled what they could control and let the score take care of itself. And sometimes the score doesn't go in your favor. So thanks for doing that.

Thanks for having me, Rob. It's been a blast to record with you these past two years. Obviously, I wish it had gone differently, but I gave this business everything I have and then some. So I am proud of the effort I put in and the work and the dedication I've had towards this business. And unfortunately, it didn't go my way this time, but hopefully next time it will. And quick reminder to all your listeners that sassmarketinggym.com is my new marketing for founders coaching business website.

First founders are loving it. It's a small tight knit group of other founders would love to have you. Thank you to Colleen for sharing not just the highlights and victories, but the real messy process of building and winding down a business. I'm looking forward to seeing what she does next.

And thanks to you for listening. If you're an ambitious founder building a B2B SaaS company, you should consider applying to TinySeed. Head to tinyseed.com slash apply to get on our mailing list and get notified the next time we open applications.