0:06

that didn't a man was going

0:08

on we i cocking

0:10

into the one only rob

0:12

walling today i'm excited

0:15

i'm excited have a feeling i haven't seen him or talk

0:17

to on and why like five years

0:19

when we last go to for hi yes

0:21

now i will micro com for it is private

0:23

like two or three years we haven't added that to my

0:25

cuffs and spend them it started but i'm pretty

0:27

sure we on to every might cough before that so

0:30

twenty nineteen

0:32

i mean what warriors yeah there's

0:34

also been on of our gas a couple times and

0:37

he's doing everything right he started since then

0:39

he started tiny seed which

0:40

is the first accelerator ver be

0:42

trap founders you still running

0:44

micro have he is

0:48

writing a book the sas playbook no

0:50

doubt about that today he also started

0:52

five or six bootstrap

0:53

companies in the past including one

0:55

that he sold for millions

0:57

presumably tens of millions of dollars drip it's

1:00

interesting talking to our because i think he's

1:02

just been around for so long that just

1:04

like the thought of rob makes me think of like all the different

1:06

phases that like tech

1:09

founder has gone through especially being and and the hacker

1:11

like

1:11

when he first started use writing start small stay small

1:14

which is basically a book to be in a d hacker well

1:16

before anybody else was like doing this in

1:19

as these kind of seen the different trends and

1:21

i feel kind of like an old man those around then

1:24

you know i like doing the stuff back then and

1:27

like the scene today's unrecognizable diva

1:29

i guess it's a guitar to keep up with like what all the changes

1:31

are and how

1:32

how the landscape is a vault i do feel

1:34

that way and i think it's the natural consequence

1:37

of starting

1:39

and the hackers and i kind of entering

1:41

this community a boot shoppers where there a bit of a

1:43

who's who right you kind of know

1:46

the the people who have been successful

1:48

but if you keep playing in that arena for long enough

1:50

like the faces change right

1:52

and like the sense of like not even

1:54

just who is doing really well but

1:57

also like what kinds of products are

1:59

the things that are gonna play well,

2:02

you just lose track of that. I mean, we've been through the crypto

2:04

phase, right? We went through like the web three phase.

2:07

Now we're sort of in this weird AI phase, the

2:09

no code phase. The creator economy phase.

2:12

And it's like, the thing is, none of these phases have gone away.

2:15

They're still there. They're just getting layered on top

2:17

of each other more and more. And each of them probably

2:19

has like its own set of superstars,

2:21

right? And it's hard for us to always be in the weeds

2:25

about who those superstars are.

2:27

Did you see Amy Hoist post on Andy

2:29

Hackers? Of course I did. A couple

2:31

days ago. I feel like I'm honored to be

2:33

one of the first commenters.

2:35

Oh yeah, you are on here. I saw a comment that had like 15

2:37

up votes or something and I looked down and it was disappointed

2:40

to see it was you. But it

2:42

was a good comment. Which she's, I mean,

2:44

I think she's feeling kind of similar. Like she's been out

2:47

of the saddle, so to speak, out of the game for a few years

2:49

due to health issues. And now she's like feeling

2:51

better. She's getting back into it. And like,

2:53

it's easy to feel like you've lost your mojo.

2:55

Especially in tech. If you're like a woodworker

2:58

and you take a break for five years and you come back, like guess

3:00

what? Like woodworking is probably the

3:03

exact same as it's been for like decades,

3:05

if not hundreds of years. But if you are in the

3:08

tech sphere and you take a break, like we

3:10

haven't been actual Andy Hackers for like six years.

3:13

And now that we are again, it's like, okay, well, like what do you, what

3:15

do we do? You know, like what do we do about AI? What

3:17

do we do about marketing channels? Like we haven't had to like

3:20

make money online in so long that it's like, I

3:23

feel like a fish out of water to some degree. I understand

3:25

that. But then I also feel like that's

3:27

the secret sauce of what makes an entrepreneur

3:29

really good. I mean, to draw it back to Rob Walling,

3:32

I remember he gave a speech and he was talking at

3:34

the microconf, one of the microconfs that we went to. And

3:37

look,

3:37

Rob Walling has done it all. He's been there.

3:40

He's written books like he's this expert. And I think that

3:42

the outside looking in perspective on

3:44

an expert on entrepreneurship is like,

3:46

this guy just has all the answers. And like when he

3:49

starts a new company, he's just going to be nothing but

3:51

like success after success and win after

3:53

win. And it's like, okay, but if you hear

3:55

him tell the story of his path,

3:57

it's like, well, here's a time that I was like,

3:59

sort of way overextended. Here's the time where I

4:02

fell into a depression. It's really just

4:05

a series of error correcting out.

4:07

I think that that's what makes someone

4:10

a really good entrepreneur because the whole

4:12

point of it is that you're venturing into some new

4:14

frontier and you're able to find

4:17

a way forward

4:19

using just basic fundamentals. Finally.

4:22

There he is. There he is. Sorry,

4:25

guys. Welcome. I've been screwing around

4:27

with my camera for the past 10 minutes. You

4:29

got to look good. You have priority. It

4:33

was just not, I was going to just be my voice

4:36

with no camera at all. I was like, this will be real good

4:38

radio. At the end

4:40

of our last episode, we were talking about like, hey,

4:42

should we do like YouTube?

4:44

Because now apparently like the distribution

4:47

is better and we're like, no, it's

4:49

always been better. YouTube has always been

4:51

better for distributing a podcast than just

4:53

being pure audio. And yet it is so

4:56

much more work. It's not like you just copy paste your

4:58

video over to YouTube and it grows. It's a lot of work.

5:00

That's what we found.

5:02

Yeah. Oh, you guys tried it? Yeah.

5:04

We tried it with the podcast. I have

5:06

a feed that is the podcast and it's

5:08

just audio. It's not a video of it.

5:11

And it has like a few hundred subscribers. And

5:13

then we even put the

5:16

micro conference talks up, which are like,

5:18

hey, this is good content. And they just get bullshit

5:20

amounts of views. You get a thousand views

5:23

for some amazing April Dunford talk. And

5:25

then we hired a consultant who was like, you're

5:27

doing it wrong. You need native YouTube content.

5:29

If you tried every time we try to repurpose

5:32

a podcast, even when we edit it and make snips, it's,

5:36

it doesn't get anything. And the ones that take off, you

5:38

know, we have videos now with, I

5:40

don't know, I recorded one that has a hundred thousand views and it's

5:42

just me talking about here are seven startup ideas.

5:44

You can get a blah, blah, blah. Right. So it's all,

5:47

it's kind of click baity stuff, but it's also,

5:49

it's, it's really YouTube native 10, 10, 12 minutes.

5:52

There's this like concept of like being

5:55

like an ancient, some ancient human tribe

5:57

where you know, you kill the Buffalo and you

5:59

use every. single part of the animal, the bones

6:02

to make your house and you use the fur

6:04

to make coats and then you eat and you just like waste nothing.

6:06

I think every indie hacker like wants

6:08

to do that for their business like if I make content in

6:11

one area I can repurpose it for every other thing

6:13

by just copy pasting it and it literally doesn't

6:15

work. Like oh it's better to just be kind of wasteful

6:17

and not

6:19

even attempt to do that sometimes. Yep. Yeah

6:21

the only thing that we've found in terms

6:23

of reuse is taking 90

6:26

second

6:28

clips and putting them on Twitter. That video

6:30

clips. Those get more, they get like five

6:33

times the engagement ish than

6:36

an audiogram of the same thing.

6:38

Anyway Rob welcome to

6:41

the show. We sort of already introduced you in our preamble

6:43

and I'm sure anyone who's listened to the show for a while also knows who

6:45

you are. How you been man? It's been a while. I've

6:48

been good. I've been

6:49

working on micro comps. I'm leaving

6:52

tomorrow for microconf Denver in

6:54

the US here and I got my book.

6:57

My book going. That's my big project. I'm heading up

6:59

right now. Channing and I were just talking about like

7:01

getting back in a game when you've been, felt like

7:03

a kind of out of the game and I know that we've been out

7:05

of the game because we haven't been doing microconf in a couple years. Part

7:08

of that is because of the pandemic but part of

7:10

that is just like you know just out of the game. So

7:12

next year Channing we should spend

7:14

our company budget to microconf. Yeah I was going to ask

7:17

if you guys were going to make it to microconf next

7:19

week.

7:20

Not next week but next year. As soon as we know

7:22

the city we'll be there because it's been a while and microconf

7:24

has like so much energy that I

7:26

miss it.

7:27

Also we're underwater like actually

7:29

becoming a real business again. I feel like

7:31

next year we'll actually like you know have the

7:35

systems and the processes in place where we're

7:37

running it. It is nice to put everything on the stripes

7:39

tab. Yeah something I'll miss.

7:42

To not burn ten grand a

7:44

month. Your business

7:46

it's like yeah I could pay this this could be my salary

7:48

you know so you got to be way more judicious with business expenses

7:50

but microconf of all expenses I think it's worth

7:52

it. You are writing

7:55

a book or have written a book how far are you in your new

7:57

book it's called the SAS playbook. It's all done. I

7:59

finished that.

7:59

months ago, four or five months. Yeah. It's

8:02

a, I have a hard copy. Got

8:05

some digital. Yeah. It's a hard

8:07

back, which is like, that's a, that's a gorgeous book.

8:09

That's a beautiful book. I paid

8:12

a lot for this. This

8:14

is one, I mean, my first book, you

8:16

know, it starts must say small as a black cover. I don't know

8:18

if you've seen it. It's an ugly as hell because

8:20

I had no budget,

8:22

no money, designed it myself. This one,

8:24

I was like, all right, I'm going to, you know, I'm going to go all

8:26

out and hire, hire a legit designer,

8:28

legit layout person, actual,

8:31

actually get an editor this time and, you

8:33

know, not edit my own work. So, so you, so

8:35

you put that together yourself. I

8:37

was curious about the publishing process. This is sounds

8:40

like independently published and you kind of put together

8:42

a team of the editor and the designer

8:45

and all that stuff. I didn't remember how much work

8:47

it was, but I knew it was going to be a lot. So

8:49

I went and found a book project manager

8:52

who used to work for a publishing project manager.

8:54

Isn't that crazy? It's very niche, but I was

8:56

like, I want, I went out just seeking if

8:58

I can find any type of project manager, I'm sure

9:00

they can do this. And if they have publishing experience,

9:03

great. And turns out she had worked for a publisher

9:05

for three years. So she knew everything. She's

9:07

like, Oh, you can buy 10 ISBNs for the price too.

9:09

So you should, you know, just all the little internals.

9:12

Oh, and I'm, I already know like four different printers

9:15

in Hong Kong and in the U S and I'm going to tell you, you know, is that type

9:17

of stuff. So it really took a lot

9:19

of load off of me.

9:21

How much money does it cost to

9:23

basically do a book, right?

9:25

Self publishing. You're hiring a book project

9:27

manager. You're hiring an editor. You're hiring someone

9:29

to, you know, design the cover to make a video

9:31

for you on Kickstarter, like how much all in

9:34

is it cost to produce a book in 2023?

9:36

At this point, I bet I'm in 30 grand, 20

9:39

to 30 grand for all the labor. Right.

9:44

That's before printing costs. Right. Fulfillment.

9:47

Yeah. It's a trick. And so that's all mostly up

9:49

front, like to get the thing produced by the different

9:51

people and then. That's right. And that doesn't

9:53

include, you know, obviously I spent a bunch of time writing

9:56

it and I had a writing coach who was busting my chops.

9:58

I haven't included her.

11:59

who wrote The Subtle Art of Not Giving a Fuck. And

12:02

they both did the same thing, where instead of

12:04

repurposing their podcast, they repurposed their blog

12:07

posts, and then just sort of edited it and put it together

12:09

in a book. And that actually works. And it

12:11

doesn't make the book any worse, it makes the book better, because you're picking

12:13

the best ideas that you've already put out into

12:15

the world, already tested it on an audience, now

12:17

you're just putting them in print format where they'll just live forever.

12:20

That's right. And I did that, so my second book,

12:22

so I've written four books, right? Start Small, Stay Small. My

12:24

second book is exactly that. It's a collection of

12:26

blog posts, and it's called Start Marketing the Day You Start

12:29

Coding. I give that one away for free on my site.

12:31

Third one I co-wrote with Sherry, entrepreneurs got to keeping

12:33

your shit together, and then

12:34

this one. But the second one is

12:36

exactly that. It's like my favorite blog

12:38

post, because I had like almost 200 blog posts at

12:41

one point, essays and such, and compiling

12:43

that into like a best of was, I

12:45

still get positive feedback about it.

12:47

I just had a conversation actually

12:50

with Josh Kaufman, who wrote the

12:52

personal NBA. He's sort of a regular

12:55

at these microconf events. And

12:58

he specifically mentioned that he's struggling,

13:00

he's working on a new book. It's gonna be a follow up to

13:03

personal NBA. And he's like, well, you

13:05

know, I've got a lot of other stuff, a lot of other

13:07

balls in the air as well. He's like working on a website

13:10

where he's gonna like have courses, and he wants

13:12

to like keep in touch with his email

13:14

list. And he's like, yeah, it's kind of hard to figure out a

13:17

way to work on any of these individual projects.

13:19

And that idea of like, well,

13:21

why don't

13:22

you figure out the topics? Just don't brainstorming

13:25

for his book. Why don't you figure out the topics that are gonna go

13:27

into your book by testing things out,

13:29

going out to your email list and kind of getting information.

13:32

So it's not just a way to like save

13:34

time once you decide you wanna put the book together, but

13:36

it's also a useful way to

13:38

like figure out what goes in the book, of course.

13:41

What resonates. And that's something big thing that

13:43

I did. I mean, we really leaned into YouTube

13:46

about a year ago on microconf. And

13:49

so I've been putting out a YouTube video every week

13:51

of unique content and it's a grind.

13:54

It's a ton of work in addition to the podcast

13:57

and all that, but the topics that resonated the most there.

13:59

I was.

13:59

pulling those in

14:01

to this book and the other

14:03

book that I haven't mentioned to anyone yet that I accidentally

14:05

wrote, there is also 40,000 words and it's like

14:08

a prequel to this. So now I got to figure out if I'm going to

14:10

publish another book later this year, but it's, you

14:12

know. Before you came on, we were talking

14:15

about your accolades and I was like, Cortland was just going down

14:17

this long laundry list and I was like, it's easier

14:19

just to start from the negative. What hasn't he

14:21

done? And now we get to add to that list that you

14:24

accidentally wrote a book? Like

14:26

what does that even mean? So,

14:29

yeah, so I had this outline,

14:31

right? And I'm like, I want to cover everything in this

14:33

ass playbook. And it's like all the way from like, I

14:35

don't even have an idea all the way to talking

14:37

about exits and mindset, you know, the whole life

14:39

cycle. So I start at the beginning

14:41

and I'm writing about ideas and how to come up with them and how to validate

14:44

and how to evaluate and how to find your

14:46

first customers and how to, you know, just all that pre-product market

14:48

fit.

14:49

And eventually the book, it was

14:51

just too damn big.

14:52

And I didn't want, I realized the more amorphous

14:55

part of it where it's kind of hard

14:58

to be super prescriptive is everything before

15:00

product market fit. Because product market fit onward,

15:02

that's what I do every day. That's

15:04

Tiny Seed, that's a lot of the higher end

15:07

microcom founders. And that's what the SAS playbook focuses on. At

15:09

least like some weak product market fit, 1 to

15:11

5K, 1 to 10K MRR. And like, how

15:13

do you then go from there? You know, rocket

15:15

ship. Everything before

15:18

that I had about 25,000 words and I was like, this

15:20

just doesn't belong here. So I just put it in a Google

15:22

doc somewhere. And then when we got done,

15:25

my writing coach and I got done writing SAS playbook, she's like,

15:27

do you want to circle back on this stuff? And I was like, yeah,

15:30

we could flush that out. Let's just add it. I think we

15:32

had a few thousand words, you know, it'll be, it'll be

15:34

done. And now it's like 40, 45,000. And

15:36

so it is, I mean, that's a 210 page book. That's,

15:39

you know, right now that tentative title is idea

15:41

to traction.

15:42

And I don't know, I don't know what I'll

15:44

do with it. Maybe I'll publish it later this year,

15:46

early next year. Well,

15:47

you did something with this book that I rarely

15:50

see and

15:51

sort of our niche, which is you launched a Kickstarter.

15:53

Yeah. You're only the second Kickstarter

15:55

that I've ever backed. Like you and one other project

15:58

in like the last 10 years and it's crushed. I

16:00

mean, you've got like, I think another week to go on

16:02

the Kickstarter and it's already at $80,000. So

16:05

it's more than recouped your initial investment. It's

16:08

basically like you've paid yourself in advance

16:11

that an author would have to go beg a publisher for

16:13

usually, but you've done it through Kickstarter, which is super

16:15

cool. And I'm wondering like why you did that? Because

16:18

I

16:18

had just never seen anyone do that. Usually people launch

16:20

on their email list or they just like host their

16:23

own sort of presale, but you've used like

16:25

this platform

16:26

that is super popular, but like what's

16:28

the advantage? Why launch on Kickstarter?

16:30

Yeah, it's a good question because I

16:32

really went back and forth on it all the way up until

16:34

the week we launched because all the books I've launched

16:36

prior have been exactly what you're saying. Set

16:39

up a landing page. Put a striped by now

16:41

link, you know, and have a few tiers, right?

16:43

There's one with a video and one with a blog. It's more expensive.

16:46

And that's how I've always done it. This time

16:48

around, there

16:49

were a couple reasons. One, I

16:52

really wanted to be able to offer a

16:54

bunch of tiers, like seven

16:56

different things. There's a live talk to Rob

16:58

option. And that starts to feel weird

17:01

on a landing page. But in Kickstarter, it's native.

17:03

It was just really obvious that I can, because like I don't

17:05

do one-on-one consulting ever, one-on-one advising

17:07

outside of Tiny Seat, but I was able to offer, I

17:09

don't know, I remember five, six,

17:11

seven slots of that. Dude, you sold out.

17:14

I know. Hundreds of dollars. You sold out immediately. So

17:16

that charged thousands. I think I should have just

17:18

offered more slots. So

17:21

I really did want to have that option of just doing

17:23

it, you know, of

17:24

seeing what happened. The second thing was, I like

17:27

learning. I like doing new stuff that I've never

17:29

done. And doing yet another launch to my

17:31

email list, that's fine. I've

17:33

done that a lot. But actually trying

17:35

to do a Kickstarter, I was like, I don't know. What does this entail? How

17:38

hard is it? What goes into it? And the learning

17:40

that I've had from that, I think, has been really cool. So

17:42

there's a bit of personal satisfaction there. The

17:45

other reason is, I've never had a hardback

17:47

book. It's always been softcover,

17:49

because hardbacks, you got to order 1,000, 2,000,

17:52

3,000, ship them over. It's

17:55

like a bunch of work. And oftentimes,

17:57

it's a four to six month delay. And

17:59

so.

17:59

Kickstarter's kind of designed for that. It is

18:02

a pre-order thing, right? I could have ordered two or 3000

18:04

books and paid for them, but I didn't want them sitting in my

18:06

garage. So this is a way

18:08

to do that. And lastly, I

18:10

view Kickstarter as a community slash

18:13

it's not quite a social network, but it's a kind of, and

18:16

I really wanted, I have exposure on Twitter. I

18:18

have exposure in podcasts. You know, I have exposure

18:20

on YouTube. I've never, I've backed 275

18:23

Kickstarter's, but I've never run one. Whoa. And

18:26

I want, yeah, dude, go to my page. It's embarrassing.

18:28

Good Lord. It is nerdy as hell though.

18:30

It's all like

18:31

video, not video games. It's like tabletop

18:34

gaming and like stuff I blew up with my kids

18:36

and there's certain slider belts

18:38

and watches that I back to, but it's a lot of nerdy

18:40

stuff. What's the, your favorite thing you bought on

18:42

Kickstarter? Ooh. Um,

18:45

you know, there's a game.

18:47

I think it was a kick, it was a crowdfunding. I'm not

18:49

sure it was on Kickstarter, but it's a game called Kingdom

18:51

Rush Rift in time that is based on Kingdom

18:53

Rush is like one of the, one of the best iPad

18:55

games and it is a tabletop version

18:58

of that with these, it's like 125 bucks when I backed it. And

19:00

it's these great minis and not messing

19:02

around endless. Just, and my kid

19:05

painted him, my 16 year old painted him and we've just had endless

19:07

hours of fun playing with that one.

19:09

You have, you have kids that you can have an excuse

19:11

for you to get those things, but I would just get them and just be

19:13

a 36 year old man. Totally. I

19:16

know. I'm

19:18

so glad that it's like having kids

19:20

is tough, but this is the best time was when my

19:22

oldest was exactly, it's

19:24

an excuse to like, I'm going to learn to play Dungeons

19:26

and Dragons again. I haven't played it since the eighties. I'm

19:28

going to get into comic books and like Star Wars. So

19:31

I would never make time for that.

19:32

I wonder thinking about Kickstarter. I wonder if there's like,

19:34

if you look at our niche, like kind of like Andy hackers,

19:37

bootstrap founders, like there's not that many places

19:39

where we launch products, you know,

19:41

it's like Hacker news, Twitter, our own email

19:43

list, product hunt, there's like only like a few.

19:45

And I feel like that number hasn't changed.

19:48

And years it's kind of just the same, you

19:50

know, especially like if you want to launch your customers,

19:53

of course, there's like lots of different channels. Like some people

19:55

are really good at SEO. Some are good on YouTube. Some are good on

19:57

TikTok, but like internally, we want

19:59

people on our own.

19:59

needs to support us. Like there's like those four places.

20:02

I wonder if there's like room for another one. Like almost like

20:05

Channing, maybe we should build this like a Kickstarter for

20:07

bootstrap founders. That's slightly different

20:09

than product hunt that has a different model, but something

20:11

that people understand. So we can kind of like support each

20:13

other and invest in each other's launches.

20:16

Yeah, and just have more surface area for like discovery

20:18

for like the discovery function. Yeah. And

20:21

I like this idea of like putting a credit card into it. Like one

20:23

of the reasons why Kickstarter is good is because people like

20:25

Rob, who've already backed hundreds of Kickstarters when there's

20:27

a new one, there's an all this friction of like, okay, I

20:29

got to sign

20:29

up and create another account and yet another

20:32

website, et cetera. It's just like, boom, click

20:34

a button,

20:35

click pledge, already in there,

20:37

payments gone. And it's like super simple.

20:39

Yep. I think that's a really intriguing idea.

20:42

There's obviously all the logistics of like, well, what if

20:44

they don't deliver and all the same crap Kickstarter has to

20:46

deal with, but the idea of bringing it

20:48

to our space, I think is a, it's kind

20:50

of a novel,

20:51

novel way of thinking about it.

20:53

I have to say, Rob, also the idea

20:56

of you going into Kickstarter is

20:58

really smart, especially, so we just had Wes

21:00

Cowell on, she runs Maven, the online

21:03

course platform, and she had this

21:05

idea where she's like, look, there's like a pyramid of

21:09

ways that you can deliver content to

21:11

your audience. And like the higher up the pyramid

21:13

you go, the more high touch and like profitable

21:16

you can get. And obviously there's higher stakes.

21:19

And she placed a book sort of toward the top of

21:21

the pyramid. You know, like the bottom is maybe like,

21:23

you know, sending a quick tweet where you don't have to defend

21:25

the things that you say. But above book,

21:27

you know, it's like an online course or you know, you're

21:30

actually live with your audience. And

21:32

with your Kickstarter, you actually get

21:35

to segment out, like you don't

21:37

just have to have this book, that's, you know, something

21:39

you've already written, there's nothing you can really add. You

21:41

get the ability to have those tiers. So

21:43

I really liked that idea as well.

21:45

Yeah, there was a microconf talk

21:47

by Ryan Delk years ago, who used to work at Gumroad

21:50

and he had the whole, the typical

21:52

launch for a book like this, is

21:55

you price it at, you have a 1X, 2.2X, and

21:58

5X price points. So if your 1X is 40 bucks, 2.2 is

22:01

what about 90-ish or 100, and

22:05

then 5X is gonna be around 200 and maybe do 250. And

22:09

then you figure out what's worth 40 bucks,

22:12

what's worth 100 and what's worth 200, right? And

22:15

that is kind of how I approached it, but also

22:17

I realized I don't wanna get

22:19

on a one-on-one call for 200 bucks, I just

22:22

gotta justify that. So yeah, there's an $800 tier, and

22:24

then there is a $5,000 tier to

22:27

come for two days to Minneapolis this summer, right? which

22:31

I think in your pyramid would just stack on top of that.

22:34

It would just be up. I've never done one of those

22:36

aside from MicroConf, so it's

22:38

certainly gonna

22:39

be an adventure, but. Are you open to

22:41

sharing how many people have taken you up on those

22:43

offers? Like how are we doing so far? So

22:46

I had five slots, and I think three are booked

22:48

for five grand a piece, which would

22:50

be a great, I mean, anywhere between three and five is like a good

22:52

number. My fear was A, it would be zero

22:54

or one. It's like, oh,

22:57

me and this person are just staring at each other for three

22:59

days in Minneapolis, but.

23:01

Do you know who the backers are? Like who got those slots?

23:03

No, I don't think we are. Total mystery. I know, it's a

23:06

trip. And you know, what's funny is my brother, who

23:08

is out in California, sent me a text, and

23:10

he's like, hey man, if I bought back one of

23:12

these in-person retreats, does that include a trip to Parlor

23:15

Burger, which is like a famous Minneapolis place? And

23:17

I was like, heck yes, it does. So I honestly

23:19

don't know if, like, one of them might be him. I

23:21

have no idea. So. It could be us.

23:24

It could be you. It could be anyone. I'll know

23:26

in nine days, I guess.

23:28

Let's talk about the book itself. You described it

23:30

as kind of what to do once

23:33

you have product market fit.

23:35

And like, obviously you have like a pretty good perspective on

23:37

this. You run Tiny Seed. You see dozens

23:40

and dozens of companies that you work with personally

23:42

every day to help them basically grow

23:44

their startups. How do you figure out what goes

23:47

into this book? Because I'm sure there's a lot of people listening, us

23:49

included, don't even want to know. Like, what do you do

23:51

once you have a big audience and your product just like

23:54

struck the market? And you kind

23:56

of have this elusive product market fit and what now?

23:58

Yeah, no, it's a really.

23:59

a good question. And it's one I'm, you know, I had

24:02

only been through once or twice before

24:04

running TinySeed. And I had been in

24:06

conversations and affiliated with folks at microconf.

24:08

But you're right, I'm really inside a bunch

24:11

of businesses now. And so I'm seeing the patterns. The

24:13

book really starts off talking

24:16

about, hey, even if you have weaker product market

24:18

fit, like here's how to think about talking

24:20

to customers and strengthening that. And you

24:22

know, it's some stuff people have heard before.

24:25

And it's also some of kind of my unique thinking.

24:28

But

24:28

then I really, I

24:30

went through all the advice

24:32

that I have emailed to founders post

24:34

I every time I would post to indie hackers,

24:37

I would take that post if it was

24:39

a response to someone's question. And I was throwing

24:41

it all this all in in a Google Doc. And

24:43

I realized there were patterns, right? There were talk

24:45

about content reuse. There were patterns

24:48

to what people were asking like, should I compete

24:50

in a really competitive niche? Like, how do I compete with

24:52

big competitors? That's a topic in the book, right? Pricing,

24:56

that's the number two chapter after

24:58

market is pricing because most founders

25:00

screw it up, right? We under price our product.

25:02

And I talked through my psychology of pricing, how

25:04

I see what I see people doing well, what I

25:06

see them doing poorly. And

25:08

then of course, marketing is

25:10

a huge one, a little different for indie hackers, because

25:12

your community much like microconf, like I don't

25:14

necessarily think about marketing beyond the content

25:16

we produce. But if you're a sass app, a B2B

25:18

sass app, like the

25:19

hardest thing is like, what do I do? What

25:21

do I try? What do I try in what order,

25:24

right? And that I have a whole chapter on that is I

25:26

have a three factor framework of like, what

25:28

is it is speed, scalability, and

25:30

cost. It's a whole mental map that

25:33

I've developed of like,

25:33

hey, there are only about 20 B2B sass

25:35

marketing approaches. These are the ones

25:37

you should try in this order based on what you

25:40

want to accomplish. Right? So it's it's

25:42

a and then I talk about hiring building your team tracking

25:44

metrics that I mean, that's kind of a high level.

25:47

So I have a friend who's an investor who

25:49

was telling me this sort of theory that it's it's

25:52

basically becoming harder and harder to build a successful

25:55

sass business. And his his idea is here's

25:57

why. There's more competition than

25:59

ever.

26:00

10 years ago, not that many people

26:02

were building SaaS businesses, not that many people knew how to

26:04

code. Tech startups seemed like a difficult

26:06

thing to bust into, especially if you're self-funded. Today,

26:09

there are like dozens of businesses

26:11

for every product idea. The playbook

26:14

for starting SaaS businesses is out, right? You

26:16

literally wrote the playbook. Other people have written

26:18

the playbooks. Like people have mapped this out,

26:21

and they kind of know how to attack a different distribution

26:23

channel, et cetera. But he argues, even

26:26

as there's more and more competition and more people starting

26:28

things, the number of channels for

26:30

marketing your product is not

26:32

really growing as quickly as

26:34

the number of people who are trying to do this thing. So everything's

26:37

becoming more competitive. Ads are becoming more

26:39

expensive. The bar is getting higher and higher

26:41

to do good SEO. Every

26:43

company is inundated with sales calls because there's

26:45

so many people doing sales.

26:47

And your experience, is this true, is it getting harder to

26:49

start a SaaS company? I

26:52

would say yes. But

26:55

it's not hopeless. Is

26:58

it slightly harder than a few years ago? Yeah,

27:01

I honestly think

27:03

everything that you're saying is accurate. The

27:05

content bar, especially with AI now, but

27:09

even before that, like 10, 15 years

27:11

ago, I could hire

27:13

someone to put out articles and just build

27:15

links, like almost buy links from

27:18

the blog networks or whatever, and you could rank in Google,

27:20

and you can't do that anymore, right? So it is more challenging. I

27:23

do think that's where raising

27:25

a bit of funding has become more

27:28

and more in my head. I think if you get traction,

27:30

it's probably something you want to think about. Even

27:32

if you're a hardcore bootstrapper like myself, yet

27:36

it just becomes hard to organically

27:38

grow business

27:40

in the ways that we used to. With that

27:42

said, there's a flip side to this. We still

27:44

see tons of companies apply to Tiny

27:46

Seed that are

27:49

competing in spaces where it's

27:51

just, the competition is much less, right? So

27:53

like Builder Prime is a CRM for

27:57

home improvement contractors. And

27:59

when I...

28:48

at

30:00

this new price point. And so I kind of feel like one

30:02

easy way to miss out is to

30:04

go, oh, well, you know, sort of, we can't build a SaaS

30:07

in this space because it's so overcrowded because

30:09

you're just looking at the market as

30:11

it's been designated by everyone who's come before.

30:14

Yeah, and that's, I just

30:16

recorded, or I think I released a podcast episode this week

30:18

about positioning. And I was talking

30:20

about like positioning really is figuring

30:23

out where there's a gap in the market. Where is

30:25

the corner of the market between, sometimes

30:28

it's like, oh, there's tools out

30:30

there, but they're too expensive and they're hard to use. Is

30:32

there an opportunity for a drip or a convert

30:34

kit to come in and kind of swoop in

30:36

under, right? And we both got a lot of traction

30:39

because of that. Or another

30:41

electronic signature tool,

30:42

isn't that a solved problem? And yet, Seinwell's

30:44

crushing it, right? And there are reasons

30:47

because he found out some unique angles, but

30:49

also because he positioned

30:51

himself well against the incumbents and people

30:54

are a little tired of them, you know? So I

30:56

think the other thing too is

30:58

it is more competitive, but the markets

31:00

are all growing. Like the market

31:02

for email service providers compared to 10 years

31:05

ago is gotta be two or three times

31:07

what it is. So there are more customers in these spaces,

31:09

even though the marketing is

31:12

more competitive, the channels are

31:14

competitive. But I think that's where people

31:16

need to have some

31:19

type of differentiation.

31:20

The biggest mistake I see is someone trying to

31:22

build the exact same thing as a bigger competitor. And they'll be like,

31:24

well, the market's huge. I just need 1% of it. It's like,

31:26

no, no one's gonna send it for you. You have

31:29

to be opinionated and either have unique

31:31

feature set or unique positioning and be like, we are really

31:33

good for this subset and not good

31:35

for everyone else, right?

31:37

I watched your video on Kickstarter where you're sort of marketing

31:39

the book and you go through like a list of different things that

31:41

are included. I wanna talk about a few of them. You know, you

31:43

have mindset, you have product market fit, you

31:45

have marketing, you have new ways to differentiate and compete.

31:48

You just mentioned that last one, new ways to differentiate

31:51

and compete. So how do you do that, right? You

31:53

said have an opinion. You can't just be the same

31:55

as the incumbent. What works

31:57

in terms of differentiating yourself and what doesn't work?

31:59

Usually early

32:02

on, everyone says, we're the simpler

32:04

version of this. And that, what

32:06

are that? Was no feature. Kind of a cop out. Exactly.

32:09

It's We're the cheaper. Right. We're cheaper

32:11

or simpler. And it's

32:12

like, okay, maybe, maybe

32:14

for now, but really that's not an, you know,

32:16

a durable advantage. Um, the

32:19

there's a couple of angles, right? The one we most

32:21

of us think of is a, to pick a vertical

32:23

is to, I'm going to be scheduling software

32:25

for these types of, for air salons

32:28

or for gyms, instead of scheduling software for everyone.

32:30

That's kind of the most obvious. Um, if

32:32

you're in a big space with kind of hated competitors,

32:35

what

32:36

you're trying to look for is where

32:38

are

32:39

their Achilles heels or where are their weaknesses?

32:41

Okay. So I'm going to use drip as an example,

32:43

even though it's, it's older, because

32:45

I did exactly this. We were undifferentiated

32:48

and we were plateaued. We did not

32:50

have strong product market fit.

32:52

And then what I found out was there at these marketing automation

32:54

providers were

32:56

pretty expensive and they were hard

32:58

to use and their

33:00

sales process sucked. They made

33:02

you go through multiple calls. They made you pay a $2,000 onboarding

33:05

upfront. A lot of them made you pay

33:07

annually. And so I kept

33:09

saying, is there a way to make

33:11

not simpler software, but much

33:13

easier to use software to remove that frustration?

33:15

Is there a way to just have self-signup if you

33:17

want it? And is there a way to still be super

33:19

profitable,

33:20

but underpriced them? Right? I'm not, I'm

33:22

not going to be Walmart, not the low price leader. But

33:25

they were charging outrageous. I mean, the cheapest

33:27

one was $400 a month and the

33:30

most of them were two grand a month and up. And

33:32

so how can we, this is a way

33:34

to do it is right. How can we take something that enterprises

33:37

are using now and paying a lot of money for and make it

33:39

more accessible to the masses?

33:41

So I think those are two. And it sounds

33:43

like if you reduce your operating expenses,

33:46

so if you have like an option

33:48

where you don't have to provide all of this onboarding,

33:50

then that's a way where you can kind of build that

33:53

into a lower price without cutting into your margins.

33:55

That's right.

33:56

It also becomes

33:58

some of the company, if you're putting against.

33:59

competing against big hated competition. Oftentimes

34:02

their cost basis for everything, including their

34:04

software. Like they were not on AWS because

34:06

they launched 15 years ago. You know, there's, there's just a lot

34:08

of, I think a lot of opportunity there. What

34:11

about mindset? This is a big topic that I

34:13

think a lot of people underestimate when they first become founders.

34:16

What have you seen that helps people have the right mindset

34:19

to basically succeed with their business? I

34:22

mean, there's a lot to it, right? It depends on your own psychology.

34:25

Like some people like me are naturally more,

34:27

um, stressed or anxious. Like I,

34:30

when I was running my last startup, it was like, I'm

34:32

stressed. Everything's going to be a deal lender. And I

34:34

had to learn to like not make speed

34:36

bumps into roadblocks. So some folks

34:38

need to hear that, that like, Hey,

34:41

is not going to end your business. Most things are not going

34:43

to end your business. Take a deep breath.

34:45

You know, we're almost trained in life

34:48

to go to school and then get a job. And

34:50

then, you know, go to, well, you go to school, go to college

34:52

and get a job. And you're not faced with crises

34:55

on a daily basis. Well, as a founder,

34:57

you kind of are. And it's sometimes I find

34:59

it's hard to pick which

35:02

of these crises are

35:03

catastrophic and which are just not that

35:05

big of a deal. Right. And so I think that's

35:07

a big thing that I help founders with these days is

35:09

I will do, do a call with a tiny seed founder and just

35:12

say, I know you're stressed and I can tell

35:14

this is a big decision.

35:15

You'll figure it out. Like, just know that you're going

35:17

to figure this out. It'll work out. You know, I

35:19

think being able to roll with things that

35:22

feel difficult, but actually realize

35:25

that they're not business sending is a big one. Where's

35:27

your mindset at nowadays? I mean, you you've

35:29

been in the game for, you know, 15, 20 years. You've

35:32

got a million things going on. Do you ever

35:34

get disillusioned? Do you feel like you have more energy?

35:36

Like, how are you feeling? I feel like I'm living

35:38

my best life and it's because I'm

35:41

working on what I want to do. So

35:44

if you look at what, I mean, and I've, I do not take

35:46

that lightly. Like I worked hard to get here. I

35:48

got a little lucky to get here, but like the

35:50

best decision I made was after

35:52

selling my last company

35:54

was to take six months off and say,

35:56

what do I really want to do? Because

35:59

I do see entrepreneur.

35:59

sell their businesses and

36:02

then start another one and do the same thing.

36:04

And they don't really want to do that. You know, it's,

36:06

and that would have been a mistake. Like if I was running hardcore

36:09

right now, pushing on a SaaS app, I

36:11

would not be happy. It's just not what I want. I

36:13

need to be doing at this stage and age and

36:16

with the age of my kids. So for me, I

36:19

looked back at like, what have I been doing for free

36:22

forever? And it was writing about

36:24

entrepreneurship and it was having a podcast about

36:26

startups and it was writing books and it was starting

36:28

a microconf, which made no money for several years,

36:31

you know, it's like,

36:32

I almost walked away from all that. At one point, we

36:34

got a cash offer for microconf and I was like, oh,

36:37

it was like 2018. I was like, oh, I could just walk

36:39

away from all of it. And then I realized, what am

36:41

I doing? That's like my legacy. Yeah. So

36:44

that's what I'm doing. I mean, that was one of the reason it was like, okay,

36:46

what if I double, I did a what if, right? What if I

36:48

double down on microconf? What if I double down on the

36:50

podcast? What if I double down on all this stuff? And that's where TinySeed

36:53

started percolating as I talked to people

36:55

of like, yeah, could you run an accelerator for bootstrappers?

36:57

And it's like, what would that look like? Right? So I

37:00

feel, I feel great these days. Quirtland, you

37:02

just, uh, you just quote tweeted someone. So

37:04

someone mentioned and, and

37:06

no, no, uh, no hate on them. They

37:08

were like, look, now that Indy hackers is independent again,

37:10

you know, if I were CS Allen and Channing

37:13

Allen, I would list,

37:14

you know, listen on microconf or

37:16

microacquire microconf and sell it again to

37:18

someone else. This time for 10 X could be a great success

37:20

story. Right. Yeah. Courtland, sheekily,

37:23

Courtland, cheekily, quote, tweets this

37:25

guy and goes, uh, the best success story

37:27

is finding work you enjoy for a lifetime. Even

37:30

if you sell and get a big, big payday, what's

37:32

next? You start experimenting and trying

37:34

to build a life you enjoy. Of course, right. That's

37:36

always the end goal. Money is a tool for that and not a destination.

37:39

There's this, um, this like,

37:41

I would describe it as a scarcity mindset around coming up

37:43

with ideas where a lot

37:45

of founders, um, myself included

37:47

for the vast majority of the time, I built stuff online, think

37:50

that like, it's very hard to come up with an idea for

37:52

something to work on that can both make money and

37:55

that can align with things that you enjoy

37:57

doing.

37:58

And so you got to choose one or the other.

37:59

And if you're a broke ass founder your first time out of the gate,

38:02

you choose the one that makes money, you

38:04

know, and you see a lot of people starting companies that they would never

38:06

want to do a second time after they sell the first

38:08

time. Do you think that that is

38:11

kind of a true dichotomy? Do you

38:13

think it's reasonable as a founder to think, okay,

38:15

what am I going to enjoy running for the rest of my life and what

38:17

will make money? Or do you think you kind of have to go out there,

38:19

build something that's successful, and then once you've got your

38:21

nest egg, then figure out what you want to do and

38:24

build a company that aligns with what

38:26

you want to do for the rest of your life? I think

38:28

that you have to enjoy the process of building

38:31

a business and

38:33

you probably want to like your customers.

38:37

But

38:37

I don't like the mindset of I have to build something

38:39

that I don't really like in order to make millions

38:42

so that I can work on what I want, right? Because

38:44

you got to enjoy the journey.

38:45

But also the journey sometimes

38:47

is not very fun.

38:48

And so what are you going to hang on to during those not

38:51

fun times when you're grinding it out or when Russian

38:54

spammers get all your IPs blacklisted

38:56

on a Sunday night has happened to us in 2014 and

38:58

I wake up and I'm like, well, guess we

39:00

had a good run. We're done. This

39:03

is true. I literally was like, I think we're done. I think we're going

39:05

to shut down. That's it. The company drip

39:07

is no more.

39:09

So like, do I love dealing

39:11

with email deliverability and IPs

39:13

and blacklists? That you dream. Yes,

39:15

no, don't. But I really

39:18

love building businesses and thinking about

39:20

them and solving hard problems creatively.

39:22

Because that was what it was constantly hard

39:24

problems that we'd have to sit down and say whether

39:27

it's like, how do we get our IPs unblacklisted or it's

39:29

how do we build like we have these 50 feature requests

39:31

and they're all kind of related, but they're all asking

39:34

for different things like how do we turn this into a

39:36

visual workflow that answers all of them? That was like a

39:38

super hard, creative, almost

39:41

engineering mindset problem to solve. That's

39:43

the part that I enjoyed the most. And so I think that's

39:46

what I'll say is like

39:48

I could have run a business for gyms or

39:51

for hair salons or whatever. It's

39:53

still creative problem solving, but I think the

39:55

two things you want to love is like

39:58

building a business, creative problem solving.

40:00

and your customers.

40:02

I think you wanna, I do enjoy working with

40:05

entrepreneurs, right? And it's like if you

40:07

don't wanna deal with hair

40:09

salon owners, then don't start

40:11

a business for them. Cause Patrick McKenzie talks about

40:13

this, right? We have a point reminder. And how Pelti-

40:16

And Bingo Card creator. And Bingo Card creator where it's like, he

40:19

did it for the money and he learned a lot. But as he

40:21

quickly learned, these are not the people

40:23

I wanna talk with every day. I think that's something that

40:25

a lot of people make

40:27

a mistake around.

40:29

There's this book Channing, remember you recommended to

40:31

me from strength to strength. And

40:33

it kind

40:34

of starts off by saying like, look, if you're reading this book,

40:37

you have made it. You are at the top

40:39

of your field in some area, you've been a success,

40:41

congratulations. But what

40:43

do you do now? This book is for people like you trying

40:45

to find their second peak in

40:48

life. And he studied all of these

40:50

famous people from

40:52

Charles Darwin to

40:55

Johann Sebastian Bach and kind

40:57

of recognized a certain pattern that when

40:59

people are younger and they're sort of getting their first success, that's

41:02

when they seem to have the most energy to sort of grind

41:04

it out and to do like this very

41:07

hard, often like creative

41:10

or even mathematical work to sort of figure it out,

41:12

right? You're trying to figure out how do I combat spammers? How

41:14

do I push into this new market? But once people get older,

41:16

if they keep trying to do that same thing over

41:18

and over, they

41:20

tend to meet with less success.

41:22

Like Charles Darwin, everybody knows him because he

41:25

created the theory of evolution. But people

41:27

don't know is that he died tremendously unhappy

41:29

because he kept trying to top that success when

41:32

he come up with new theories. It's just no one ever really knew anything

41:34

about when he sort of died alone and unhappy versus

41:37

others, which is tragic while you're

41:39

laughing. But I

41:41

think that's common. It's so tragic. But I

41:43

think the more successful approach that he talks about

41:46

is as we get older and we have

41:48

gained all this knowledge from our earlier

41:50

wins is to move into a much more social

41:52

role, a much more teaching role, a

41:55

role that aligns with our strengths, which

41:57

as we get older is the fact that we have a ton of experience.

41:59

and wisdom and knowledge, much more

42:02

than anyone younger has because they just haven't

42:04

been out there. Whereas at the same time our brain

42:06

power, our horsepower is slowing down quite

42:08

a little bit. We're a little bit more resting on our laurels.

42:10

And so it's not surprising to me to see this transition

42:13

of a lot of people who do this crazy

42:15

SAS startup at first and they're fighting through

42:17

all these thorny problems that aren't really their life dream. And

42:19

then later on when they look back and see what they enjoy when

42:21

they want to get started again, it's running

42:23

conferences, doing one-on-ones and office

42:26

hours and talking to people and just generally

42:28

giving back and helping other people.

42:30

And once you've sort of achieved that nest egg, like you also

42:32

have the clout to do that and to make

42:34

money from it

42:35

because people will pay you $5,000 to go on a retreat with

42:38

you because you have those wins under your belt. Yeah,

42:40

I'm really honestly impressed or surprised

42:42

by the people who do just keep starting and starting

42:45

like David Kansol's on his fifth, I think

42:47

company. And even like ADP

42:50

and R did Woo themes,

42:52

which became WooCommerce and they did Converseo

42:55

and sold that to campaign monitor. And

42:57

now it's on like his third or fourth and he had a couple that failed.

42:59

And I'm like, I respect that, but

43:02

that's not me. But I'm

43:04

also a lot older than AD,

43:05

I think. So David Kansol is just an

43:07

anomaly to me. I'm like, this guy's unbelievable. But,

43:10

or even like, I guess Jason Cohen had

43:12

three

43:12

and he had like a small

43:14

success upfront and then a bigger one. And then

43:17

WP Engine has been the last 12 years. But

43:20

I couldn't see him doing another one after WP Engine,

43:22

but maybe he would. But I see

43:24

exactly to your point, I see a lot of entrepreneurs doing

43:27

that. I mean, there's a reason the Tiny Seed mentors,

43:29

the mentor list is a lot of founders who

43:31

have exited because they want to participate

43:34

and give back and still be in the game, so

43:36

to speak. But they don't wanna be

43:38

the, they know it's like, it's

43:41

a cliche, but like, I'm too old for this shit. That's

43:44

how I feel of actually being in the heart of it. I've done it for

43:46

too many years and like, it doesn't sound fun. Could

43:48

I do it? Could I pull it off? Yeah, do I wanna

43:50

do that? No.

43:52

These days I'm curious about you. What

43:54

drives you? Are you driven by making

43:57

more money a lot?

43:59

just sort of the process. Yeah,

44:02

because I think everyone has kind of their own formula

44:04

for like what brings happiness, what motivates you. Right. Like

44:06

when I was younger, I was just like, I wanted to be a success. I

44:09

think now we're sort of talking about like the second peak in

44:11

your life. And it's like a lot more driven

44:13

for most people by like what makes me happy. What's

44:15

on what's on your checklist for what makes you happy? Yeah,

44:18

that's it's a really good question. And it's one that

44:21

like I grew up my whole life wanting

44:23

to be able to work on whatever I wanted.

44:25

I wanted freedom. Right. I never the money never mattered,

44:28

but I needed money to be free. And of course,

44:30

it's like a constraint, not a goal. It is

44:32

exactly. For me, it was doing it. Yep. And so my

44:35

goal since I was like, had my first

44:37

job, you know, when I was a teenager was like, I

44:39

want enough money that I never have to work again.

44:41

That was it. And no, and I don't need more. Some people

44:44

do need more and they've driven by the money. And I haven't

44:46

been. The money is nice. I have a, you know,

44:49

house in a car and that's great. But I

44:51

achieved that point in 2016, in essence, where

44:56

it's like, OK, I literally never have

44:58

to work at it, but I'm going to work. So what

45:00

am I going to work on? Right. And that was the big kind

45:03

of come the Jesus moment, so to speak of like, I

45:05

went on a founder retreat and was like, I

45:07

think I'm going to step away from all this. And I actually started talking

45:10

to the number two

45:11

board game slash tabletop

45:13

gaming website in the world in terms of traffic

45:16

and reach. And I was going to acquire it from him. And

45:18

I

45:18

was like, how much revenue do you have? I

45:20

was going to go all in on tabletop games and all this. And

45:22

then I

45:23

had that moment I talked about earlier. I was like, no,

45:26

I mean, that's fine, but I'm going to regret

45:28

this if I do this. Oh,

45:30

yeah, I would get into tabletop gaming and be happy

45:33

for a couple of years. And then the margins

45:35

are terrible. You know what I mean? Money

45:38

is still a scorecard. You know, it is. That's

45:41

something I think is a pro

45:43

and a con or a strength and a weakness of me

45:45

is that I have a tough time doing things that don't involve

45:47

money, even though the money doesn't motivate

45:50

me per se. But just doing things,

45:52

even like my hobbies,

45:53

I collect, you know,

45:55

collectibles, right? I have this Beatles gold record back here

45:58

and I bought it and it's worth more than.

45:59

used to be and it's like I'm never gonna sell it so that doesn't

46:02

matter but somehow the money likes it

46:04

is a little little jolt yeah makes a

46:06

little wiggly

46:08

yeah I know my checklist one of the I've got four

46:10

or five like items on it that tell me like I'm

46:12

gonna like working on this and one of them is that there

46:14

has to be some number that goes up

46:17

I don't know why I don't know where that comes from it has

46:19

to be like if I was a writer maybe it wouldn't be money

46:21

maybe be like the number of readers or copies sold or something

46:24

but like if there is no like cumulatively

46:27

growing thing then I just get

46:29

this weird feeling in the back of my head like I'm not really building

46:32

anything like what's the purpose and so like

46:34

money in a way like when it ceases to become like the primary

46:36

motivator it's no longer like I need more money to be free

46:39

it does become like this kind of scorecard but

46:41

like there's healthy and unhealthy ways for that to happen

46:43

I think if it's you know like you're the Scrooge

46:46

McDuck character and

46:47

you're just collecting more and more money but you're unhappy because

46:49

you have no idea what you want to do with it except put it in a room

46:51

and like you know swim through your vault of gold

46:53

coins then like yeah it's like that's unhappy

46:56

and that sucks but if it's like okay well this is like a

46:58

way for me to measure my progress and feel good

47:00

like I'm accomplishing something then I think you can

47:02

be healthy

47:03

and you can always spend your money to like do other things right

47:05

invest in other entrepreneurs pay it for

47:08

help out friends and family etc because it's not about

47:10

like spending it on yourself that matters it's just

47:12

a sort of a motivational motivational thing

47:14

yeah I think that's a big one a number

47:17

going up is something I think about a lot too

47:19

and this is gonna sound

47:21

maybe contrived or cheesy or whatever but

47:23

like when I I realized at

47:25

a certain point I really like making an impact

47:28

I really like impacting people and the

47:30

more people I can help or impact the

47:32

happier I am and that's

47:35

not just bullshit talk like if you look at my history

47:38

I grow the podcast so that more people every time

47:40

I get an email that's like thank you like I get these emails

47:43

it's like you changed my life I know what I was

47:45

doing I built an MVP I just sold

47:47

it like there was a guy in Romania or somewhere very

47:50

low cost of living who's like I just sold it right half a

47:52

million dollars I can almost live the rest of my life on

47:54

that and it was basically following your advice I

47:56

made no money off of

47:57

that they've never come to a microconf I

47:59

don't care. I care that his

48:01

life is better. And I, is that a

48:03

bit of a luxury? Yeah, I have that. I don't

48:06

need to make money off him. Right. But that's

48:08

where the numbers that go up these days are,

48:11

you know, YouTube

48:13

subscribers or podcast subscribers. Like that's

48:15

where I'm if those are stagnant, I'm just like, who, so

48:17

who am I helping then? Right? What good is this?

48:20

How am I making a difference in the world? Right. So

48:22

yeah, I wanted to ask you guys about the whole Stripe

48:24

thing. Is it a word transition to, to do

48:26

this? Yeah, let's talk about, we can talk about whatever we want.

48:28

Yeah. So I love interviewing another podcast host

48:30

because you could just, because we can just turn the tables. Yeah. Exactly.

48:33

Well, I mean, so I listened to your last episode. I saw

48:35

the announcement that your indie hackers

48:37

is indie again. I listened to your last episode and

48:40

I,

48:41

I know you can't divulge details

48:43

of the, of the deal, which I'm not going to ask about, but

48:46

I totally get why you guys would do this. Cause

48:48

I would feel the same way, right? I know even

48:51

no matter how good the parent company,

48:53

that's the question. Right. Right. Why was, and

48:56

I believe that Stripe approached you about

48:58

it.

48:58

So is it a focus thing? Like I have my own theory

49:00

of like, well, you know, markets are going down. I know they

49:02

took a haircut on valuation or they just

49:04

trying to focus or what's, what's

49:06

the logic there? I think it's, it's

49:08

tricky to talk about your right. But

49:10

I think at the end of the day, like I know this also

49:13

sounds cheesy, but like people

49:15

that Stripe are just really good. They

49:18

are not very miserly. They're

49:20

not like penny pinching, trying

49:22

to save every nickel and dime. And I think Patrick

49:24

in particular is pretty wise about like the overall

49:27

sort of concept of like branding and reputation, you

49:30

know, compared to other like big unicorn startups of

49:32

its size, Stripe has remarkably small

49:35

number of like bad press stories, et cetera.

49:37

And like that's, that's like deliberate. It comes from the top

49:39

because everyone at Stripe is conscious of

49:41

like making sure like we have what's called like the front page

49:43

test, right? If what you're doing appeared on the front

49:45

page of a magazine, how would you feel about it for

49:48

the company? Right. And that takes precedent over,

49:50

okay, how much money do we save this quarter or this

49:52

half or something? And so I think for Patrick,

49:55

he's just looking at any hackers and looking at like who we are

49:57

and what we're motivated by and how we feel. and

50:00

a large part of it is like, hey, are you guys

50:02

happy? Are you doing what you want to do? You still have the

50:04

same fire, you still have the same drive? He's asked me that

50:06

question

50:07

every single year

50:09

that we've been at Stripe. And

50:11

I think we could have stayed, right? We could have

50:13

just continued doing exactly what we were doing. And

50:15

Channing and I had also go back and do some soul searching and

50:17

be like, are we happy? Would it be better if we

50:19

owned Indie Hackers? That was never an option before. What

50:22

would we do in that case? And what would we need

50:24

to feel like it was even a fair deal or a good

50:26

deal because Indie Hackers burns through a lot of cash,

50:28

right? I don't want to jump ship and then suddenly be

50:31

losing money every month. And

50:33

so I think it was just like a hodgepodge of just, it

50:36

was just convenient for both parties to figure out a

50:38

good deal for that.

50:39

And here we are in this crazy

50:41

situation where we're like, we owned,

50:44

this time last month, 0% of Indie

50:46

Hackers, right? And now we own way, way,

50:48

way more than that. Another thing from Stripe's

50:50

incentive perspective just aligns

50:53

with the weird circumstances

50:55

around them acquiring us in the first place, which is

50:57

that we inspire a lot

50:59

of new entrepreneurs and we help

51:01

to educate a lot of entrepreneurs to be more successful.

51:04

That's a common rising waterline

51:07

that lifts all the boats, right? And so that's

51:09

what we were doing at Stripe. We weren't making

51:12

a lot of revenue and then it wasn't a financial

51:15

acquisition that we were raising

51:17

their bottom line in that way. Like if we

51:19

are

51:20

healthy and happy and like inspiring

51:22

more entrepreneurs and like doing what we are

51:24

really like designed to do better

51:26

than that helps with what Stripe actually

51:29

wants from us. So

51:30

like us

51:31

being cut loose, us being independent

51:34

and like having the energy to

51:36

go 100% on Indie Hackers like

51:38

is directly in Stripe's interests. Yeah,

51:41

and that's a really mature way of thinking about

51:43

it. And I would expect that Patrick or

51:45

Stripe in general to think about it that way, right? It's

51:48

a long-term way of thinking. It's as

51:50

you said, I know they talk about, raising

51:52

the GDP of the internet. And if you're able

51:54

to do that better independently, as

51:57

I was gonna say before you said it, I'm like, I know

51:59

Stripe's not making.

51:59

and buckets of money off indie hackers. So that

52:02

was not the play. The play, as I saw

52:04

it years ago, was, hey, we

52:07

want indie hackers to stay alive. And

52:09

or I think at the time you were running ads, and I think

52:11

Patrick was like, ah, it'll grow faster without ads.

52:13

That was my mental model of why they acquired you. It

52:15

was like, they want Microconf to exist. They want

52:18

indie hackers to exist. I

52:20

don't know if you guys were there at the Microconf where

52:22

I was either talking to Patrick

52:25

or John Carlson on stage, and I said,

52:27

raise your hand if you know SaaS companies

52:29

are bounding, right? And raise your hand if you use Stripe. And

52:32

it's like 90% of the intent. It was crazy,

52:34

right? I totally get that it's

52:36

good for them. It's just such a mature. Companies

52:39

don't think that way. And that honestly

52:41

is one

52:41

of the reasons. I have respect. Collisons,

52:43

man. Tons. Just loads. They

52:46

run it. I have similar respect for

52:48

Ben Chestnut at MailChimp. There's only a handful.

52:50

Darmash at HubSpot. There's a handful that I'm like, you

52:53

are super legit and you are very wise.

52:56

And you make decisions that are very mature.

52:58

I have, I mean, a mental

53:00

model, but it's just borrowed from other things. Like

53:03

Jeff Bezos has the regret minimization framework

53:05

when you come to a decision. Which am I going to regret least?

53:07

In my head, it's usually if

53:10

I come to a hard decision, if

53:12

I pick the path that will

53:14

let me either learn more or that's riskier

53:17

within reason. Not risky like putting my house

53:20

on the line, but that kind of scares

53:22

the shit out of me. Those are the

53:24

ones that I tend to lean towards. I

53:26

wasn't able to do that in my 20s. I was too scared. And then

53:29

as I matured, I was like, oh, risk

53:31

actually brings fun. It

53:33

brings a little bit of- Stakes in there. Yeah,

53:36

so I mean, the two of you as founders,

53:38

as entrepreneurs, I feel

53:40

like you would have regretted not going

53:43

independent. I just can't imagine not

53:45

doing it. Even though it's scary and you have to work through it

53:47

as an emotional process, it doesn't

53:49

even seem like a decision to me. It's just a

53:52

foregone conclusion that you would do this.

53:55

What would you do in our situation? What do

53:57

you want to see us do? A lot of people have asked about Andy Hackers.

53:59

investing and other indie hackers.

54:02

In fact, Eric Torrenberg DMed me

54:04

like

54:05

three months ago. He started on deck, which

54:07

is sort of this like school for people in the tech industry to

54:09

sort of help each other with these different topics. And he's like, Hey,

54:11

why isn't there a way for people who love

54:13

these small indie projects to basically support each other financially

54:16

and invest in each other? And, you know, I'm

54:18

not sure how it would work, but like, why haven't you figured that out? And

54:21

it's been in the back of my mind for a long time, but I haven't

54:23

just sat down and thought like, how would that work? And

54:25

Rob, you're like the best person to talk to me about this, because

54:27

like you actually invest in like, quote

54:29

unquote bootstrapped startups, right?

54:31

Like you see like, what are the returns like? How does it actually

54:34

work? And I

54:35

think no one's really cracked this nut because like, generally

54:37

speaking, people invest in tech companies hoping

54:39

for a unicorn.

54:40

And the average any hackers not trying to make a unicorn,

54:42

right? They're trying to like,

54:43

pay their rent.

54:45

And so it's something that my noodling on is like, is there some

54:47

way to financially, because like,

54:49

partly, it's just like fun, if I could go to a giant directory

54:52

of indie hackers and see all my favorite people building their

54:54

stuff, and I could throw money at them to help them

54:56

be able to take off work and launch earlier, et cetera,

54:59

and expect like,

55:00

not some huge return, but something

55:02

that's like, it makes it somewhat worthwhile. That

55:05

would be dope. I'm not sure what the numbers

55:07

are like for that though. Like, you know, realistically,

55:09

is that even possible to get a return? There's two

55:11

complexities that I'm going to introduce. I love

55:13

this idea as well, because I would love

55:15

to go to a directory of indie hacker projects

55:18

or microconf projects and just be like, a hundred bucks,

55:20

five hundred bucks, whatever. This is great. This is super

55:22

fun.

55:23

I think there's two things that are going to get in your way. We're going

55:25

to make it complicated. Number one,

55:28

return drivers, making your

55:30

money back will be very, very difficult. Even

55:32

if you, if you go across all these indie hacker

55:34

projects, as you said, people are trying to make

55:36

their rent and maybe they make, you know, maybe

55:39

they get to 20

55:39

K or 30 K the money that's

55:41

thrown

55:42

off from there, just isn't a lot.

55:44

Right? So the valuations would have to be very,

55:46

very, I'll say they'd have to be very

55:48

reasonable compared, you know, it's

55:50

like if you raise it a million dollar valuation and you

55:53

put in a thousand dollars, you own one, one

55:55

thousandth of that company. And

55:58

so as you throw dividends off, like we can do. quick math

56:00

is nothing, right? So then it's like, so

56:02

you can't raise it a million. So you got to raise

56:05

at a, maybe a hundred thousand valuations.

56:06

So then you put it,

56:07

you know, and will people allow that,

56:10

right? Will they say I'll sell 20% of my indie

56:12

hacker project for 20 grand. Um,

56:14

so that's one thing like is to make the economics

56:16

work. It will have to be different than certainly

56:19

than Silicon Valley, but even than like the tiny

56:21

seeds in the indie. You would be

56:23

at a level. Diff,

56:26

I would say a level lower just in valuations

56:28

in order to make the economics ever work. The

56:31

other thing is on the,

56:34

my God, the laws in this country, the

56:36

securities laws, we, we

56:38

struggle. So we spend so much money

56:41

on lawyers and we are literally

56:44

lobbying Congress to try to get the 99 investor

56:46

rule changed. Right. We, we raise,

56:48

we've raised a fund. We can only have 99 investors. They

56:50

all have to be accredited.

56:51

They're already accredited. There's

56:53

a millionaires and yet I can't have more than 99 people

56:56

in that fund. It's ridiculous. Right. So we, we're

56:58

working with a group to try to get that change, but all

57:00

that said, so

57:02

we in your case with indie hackers, I think you'd

57:04

want to go more of the red CF, the crowdfunding

57:06

route, right? Right. Cause then you can just put

57:08

in a few hundred bucks because if you were to try

57:10

to raise from accredited investors, a there's just

57:13

only so many and B

57:15

if you raise a thousand dollars from an accredited investor,

57:17

like the legal fees alone to just put that together

57:20

are our cost prohibitive, right? Yeah. So

57:22

I think with crowdfunding, I

57:24

would then logistically like

57:26

want to go out to one of the crowdfunding platforms

57:28

and partner with them, almost like you'd have a

57:30

crowdfunding syndicate,

57:32

you know, like syndicate is you go on

57:34

Angel list, right? And we run this, we

57:37

get a SaaS deal and they're outside of

57:39

tiny seed, but they're in the tiny seed syndicate

57:41

and we can raise a hundred grand, 200, 300 grand

57:43

to help them kind of raise a round

57:46

from our investors now in

57:48

a syndicate, they all have to be accredited and I don't

57:51

know. That's the best

57:52

idea. I don't know that that's the best option for indie hackers,

57:54

but I've never seen a crowdfunding syndicate.

57:56

And I don't know if that could exist

57:59

because you don't. You don't want to deal

58:01

with the legal, trust me. Right, I know. It

58:03

is mind boggling how it's expensive

58:06

and time consuming. Talk about stuff we don't

58:08

want to deal with. It's the worst.

58:11

It seems like crowdfunding sidesteps

58:13

so many of those issues. You get to invest,

58:18

let's call it invest, but you're not necessarily only

58:21

just buying equity. You allow

58:23

for, say, the founder of

58:25

a company to innovate what they want

58:28

to give people such that maybe there are

58:29

way easier returns

58:32

like, hey, if you invest

58:34

this much money, they can do the tiers, right?

58:37

Then you can be someone who has

58:39

access to these features

58:41

for my product. Or you can always

58:44

have you on this page. Who knows, right?

58:46

But it just allows for some innovation

58:51

on the kinds of returns. And so

58:53

we talk about markets and the personalities that

58:56

go into markets. Well, it just so happens that if

58:58

this happens on any hackers, you're dealing with people

59:01

on the supply and the demand side who

59:03

are very, have a lot of initiative, have a lot of

59:05

creativity, and have a

59:07

lot of goodwill with one another. So

59:10

if you remove equity, it becomes a lot simpler.

59:12

And if you go to the more, you talked about doing

59:16

a crowdfunding model that is an equity, more of a

59:18

Kickstarter model built into the Exactly.

59:21

That's where you get back to,

59:22

I could see people needing, it would

59:25

be a brand like you're the most famous

59:27

indie hackers who,

59:29

it's like John Young Fook, right? He's big on the side. I'd

59:32

expect, is Peter Level's a big en-act, right? So

59:35

if they came on and we're raising, a bunch of us

59:37

would throw in money. I think people who have

59:39

done less work and who have less of a following

59:41

might struggle a bit

59:42

more, but that would be the, that would kind

59:44

of be the game, right? Yeah, that's the game. Can

59:46

you discover the diamonds in the rough? You can be

59:48

there when no one else is. Anyway,

59:51

Rob, thanks a ton. I appreciate your

59:53

ideas and your feedback. I

59:56

feel like we can work together in ways that we haven't been able

59:58

to in the past, which is kind of cool. We're just

1:00:00

in a whole different playing field now. And so, excited

1:00:03

to go to a microconf next year. Excited to stay in touch.

1:00:05

Excited to talk to you about being an investor, because I think I might be

1:00:07

an investor going forward. Tried just to their tender

1:00:10

offer. And so, my money

1:00:12

is no longer just all on paper. Just gonna say, yeah, now

1:00:14

you're rolling it. That's great. Yeah, yeah. So

1:00:16

life's exciting. I'm excited for your new book. I ordered, I think,

1:00:19

the option on Kickstarter to give me two hardcover copies.

1:00:22

So I can give one away. And then I think the audio book

1:00:24

or the e-book.

1:00:25

And then I'll probably buy whichever one I didn't get

1:00:27

afterwards, because I want every format possible.

1:00:30

Yeah. Well, and you know how I can tell that

1:00:32

we're beyond the Stripe Tinder offer? For

1:00:35

once, you're not wearing your robe. You're wearing an

1:00:37

actual shirt. I can afford

1:00:39

clothes. Or it's either the money, or

1:00:42

you just have a lot of respect for Rob, because you really

1:00:44

dress up today. He doesn't need to see your

1:00:46

hair cast. You have a whole t-shirt on.

1:00:48

I subjected Wes to my robe

1:00:50

look today. Rob, you get

1:00:52

to see me fully clothed. Thanks

1:00:54

a ton for coming on, dude.

1:00:56

What's your parting advice to people listening

1:00:58

who are trying to figure out what to do now

1:01:01

that they've hit product market fit? Is this where

1:01:03

your head's at nowadays? Besides

1:01:06

just buying your book, which of course they should go out and do, what's

1:01:08

something you want founders to take away from your learnings?

1:01:11

One thing I really regret is I didn't

1:01:14

delegate more. I did hire

1:01:18

more senior people. I hired a lot of junior people, because

1:01:20

I didn't have money. And I was always

1:01:22

the bottleneck, right? Managing junior people. And

1:01:24

I think one thing that's on my mind, these

1:01:27

days is the luxury that I have, we talked about earlier, of being able

1:01:29

to work on what I want is because we have very senior people.

1:01:31

And so the moment you can hire

1:01:34

someone who's really good, even if they're expensive,

1:01:36

and that will allow

1:01:38

you to tend to business. Feels amazing

1:01:40

hiring somebody who's good. And then suddenly all this stuff is

1:01:43

getting done, and it's getting done better than you would have done it.

1:01:45

And you're just like. It is.

1:01:47

It's crazy. That's awesome advice. Where

1:01:49

can people go to find more about you?

1:01:52

Start off with the rest of us, if they want to listen

1:01:54

to podcasts, or Twitter at Rob Walling. So

1:01:57

I was highly recommended, one of the longest running podcasts.

1:01:59

in the space, super good.

1:02:01

Rob's silky voice coming

1:02:04

through every episode. All

1:02:06

right, thanks Rob. Great to be here. Thanks

1:02:08

for watching. Bye. Bye. Bye.

1:02:12

Bye. Bye. Bye.