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Brutally Honest Business Advice to my Younger Self

Brutally Honest Business Advice to my Younger Self

Released Wednesday, 10th April 2024
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Brutally Honest Business Advice to my Younger Self

Brutally Honest Business Advice to my Younger Self

Brutally Honest Business Advice to my Younger Self

Brutally Honest Business Advice to my Younger Self

Wednesday, 10th April 2024
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0:02

What is up you sexy bastards? It. Is

0:04

your boy? Ice cream? sprinkles? A

0:07

rap I can't Lose aka a know

0:09

Kagan who comes up with these names

0:12

that today is the next part of

0:14

our brutally honest series. We've. Heard

0:16

amazing feedback from this and today we're

0:18

shifting from career advice in the previous

0:20

episode which you can check out to

0:22

business advice. Careers. Are like

0:24

dipping your toes in the water. But business

0:26

is where the real cash flow happens and

0:28

you know me. I like the

0:30

hustle. I like the dollar bill. Now. I'm

0:32

German back into my miata two thousand and

0:35

four time machine to know as back to

0:37

the future dose where I'm sharing my best

0:39

business advice. I wish I knew back in

0:41

the day and hey I do believe it

0:43

will help you to in present day. People

0:45

are always hustling to reinvent the wheel and

0:47

create new paths in business. But the best

0:49

path? Has already been figured out. Don't

0:51

try to be innovative nine or ten times, Copy

0:54

nine out of ten in innovate one outta ten

0:56

times. So listen up my sweet letters. Here's three

0:58

gigantic things. You can be taken away. Number One.

1:00

Should. You be following curiosity or

1:03

opportunity. Number. To.

1:05

Find. People who are already saying yes to

1:07

a sale And how do you build a business

1:09

around them? And number three. How. Do you

1:11

get balls rolling and sustain in success

1:14

were integrate those three things plus twenty

1:16

plus more your nuggets along the? If

1:19

you like this episode, any want more brutally

1:21

honest advice about getting started your career? check

1:23

out episode Three Forty Six in this feed

1:25

as well semi feedback at. Know occasion

1:27

on Twitter or Instagram. And. Let

1:29

me know you think these brutally honest episodes.

1:32

It. A spring break at App sumo.com and of

1:34

your member Spring Break if you're too old for

1:36

but you are not to the party and to

1:39

celebrate we're running some insane like deals As usual

1:41

for twelve different products, the help you run your

1:43

business on App Sumo normal monthly subscriptions. These aren't

1:45

lifetime deals so hopefully you live forever and use

1:47

a products forever and you never have to pay

1:50

for them again. Your. Solar Printer or you're running

1:52

a business you want to save money in her costs. You.

1:54

Go check them out and enjoy! Had app

1:56

sumo. Dot. Com y'all if you're not

1:58

a my mailing lists. We. Exclusive enough each and

2:00

every week. Go to know, have taken.com and sign

2:03

up today. I think you're gonna be some juicy

2:05

business nuggets for you to enjoy. Also

2:07

special pre show shuttle asserts that Sabal

2:09

fast as go. I always look forward

2:11

to my run listen to the show

2:13

with No and Death along feel good

2:16

vibes it loads of juicy insights. Thanks

2:18

bro Only from Run Seven seven.run think

2:20

you fat fall for that! Amazing feedback

2:22

and great review and thank you everyone

2:24

you Borgias listeners I love been your

2:27

ear lobes. I want to shout you out

2:29

in a future episode of you've Got a Book is gotta your

2:31

L If you're working on something, let me said you at. All.

2:33

You have to do is the the view on I tunes. Eur spotify

2:36

at what you think of this episode in the show.

2:38

Checked every single one of them letter said he out

2:40

in a future show. So.

2:44

In terms of. What mistakes

2:46

did you make before you

2:48

learned? I think a huge

2:50

mistake was not realising that

2:52

everything I was doing was

2:54

actually meeting me somewhere. So.

2:56

I was swinging all the time. almost made

2:59

too much. and I wasn't just realizing that

3:01

each of them had something to teach me.

3:03

And so as you are doing different things

3:05

in your business, And. It's not working.

3:08

Stop. For second say thank you friend for

3:10

teaching me something interesting about what's going on.

3:12

So I was swinging a lot you know

3:15

I swung each of D Consulting do in

3:17

marketing for college campuses while I graduated I

3:19

didn't injure card or com a discount card

3:21

or which was a swing at a college

3:23

up.org which was another swing which has Craig's

3:25

list for people Edu email addresses college students

3:28

that I swung with entrepreneur twenty seven which

3:30

was just meet up some hangouts of other

3:32

people. And. Then I swung on Community

3:34

next because I wanted a conference for social networking

3:36

and there wasn't one. And co

3:39

that three next than led

3:41

me to mint.com. And. Mint or

3:43

com Let me to do pick flip. Which. Was

3:45

face for games and kick flipped Led me to

3:47

do gambit which is payments face or games. And

3:49

Gambit Them led me to ultimately end up

3:51

doing up Simmer which has become my life's

3:53

work. and so on the swings are

3:56

actually a great learning opportunities if i just

3:58

looked at them as learning moment And

4:00

there's just a lot of things that I hated

4:03

along the way that all were learning moments too.

4:05

You know, I did the payments for Facebook games

4:08

and I learned about the power of

4:10

partners, right? Like who are you really

4:12

marrying? When we talk about business and we're like I

4:14

need a co-founder I'm like do you really want a

4:16

co-founder if you don't find the right person? It's gonna

4:18

be a big pain in the ass or as my

4:21

grandma Mima would say they need to talk us So

4:24

that was a great learning opportunity where me and the

4:26

partners each thought we were more important than each other

4:28

and it turns out We're all the most

4:30

important just maybe not all together and so that was

4:32

a great learning moment Another part from

4:35

gambit as well even just breaking down

4:37

more specific examples was it was a

4:39

really great sale cycle So the business

4:41

model matters so specifically with gambit

4:43

It was a really cool business model where we

4:45

built this payments engine and literally you plug it

4:47

into the games and instantly we made cash So

4:50

from a business model perspective is really

4:52

powerful to realize about getting paid upfront

4:55

being close to the money is important

4:57

But there's also an opposite side of that which

4:59

was some of the sales cycles for larger clients

5:01

like Zingas of the world Disney of the world

5:03

play them of the world storm into the world

5:06

could take six to twelve months a Lot

5:08

of ass kissing they would put us in we'd

5:10

start getting rich and then they would take us

5:12

out two weeks later And it really

5:14

helped teach me in business the value of what's

5:17

most important to my customer And if you're gonna

5:19

do a long sales cycle, it's got to be

5:21

a long reward Short

5:23

sales cycles quick reward and those

5:25

were really valuable lessons along the

5:27

way that kept teaching me different

5:29

pieces Same thing from the conference

5:32

stuff that I was talking about earlier as

5:34

I was doing entrepreneur 27 as I was

5:36

doing these conferences I was looking up through

5:38

some photos on Flickr. I know y'all don't

5:40

know about Flickr anymore I had hair when

5:43

there's Flickr and I was like, holy shit.

5:45

I did wine meetups. I did chess meetups

5:47

I did ping-pong meetups. I met

5:49

you know, the founder of Firefox and I was

5:52

connecting with Michael Arrington from pet crunch and

5:55

You Know those swings were really great at getting

5:57

me just to be around other interesting people. And.

6:00

So I your lot of people Noah were you have

6:03

an audience now and I love my audience. I love

6:05

each of you. You're all my favorites! But.

6:07

It was starting the same way that everyone elses the

6:09

don't have an audience by going out there and and

6:11

trying to meet people. Maybe. One hype

6:13

piece of business advice brutally honest that

6:16

I think I did correctly that I

6:18

would do again is really follow your

6:20

curiosity and really go after problems you're

6:22

excited about. When I ceased opportunities when

6:24

I chased, let's say today Ai are

6:27

furious. Goes Crypto or Lazarus era shopify

6:29

are you know, like And I don't

6:31

think it's bad. I definitely have chase

6:33

but when I've chased the opportunity I

6:35

flamed out. And when I chased my

6:37

curiosity and when I taste the problem

6:40

solving I stuck with. So. Content

6:42

creation, him, blogging and all this parts

6:44

was hugely advantageous. My love doing it

6:46

and I've stuck with a twenty four

6:48

years. Whereas and I did face or

6:50

games can like wanted to get the hell out

6:52

of mint.com or I would you know as I

6:54

chased payments for these games same kind of vain

6:56

or as i chase affiliate side and built free

6:58

calls to.com. It. Was really easy to give up.

7:01

And. So I've just be mindful. the proms you're

7:03

chasing acknowledge the chase and be okay with it

7:05

and really be thinking. It's. A chase and

7:07

I'm just here learning business skills. It's a cheese

7:09

and using repetition to improve my skills to get

7:11

me to the point of what I want. Now.

7:14

On the other side of the taste was really

7:16

great proms as excited about. When. I got

7:18

the job at face because only because I

7:20

was using Facebook a lot in my consulting

7:22

business h of T to do marketing college

7:24

students. And I was using it to like

7:27

communicate with people and saw like man I love this

7:29

site so if I'm it's either going to be quit

7:31

my job, it in full surround business or go work

7:33

here. So same thing with mint.com where I was like

7:35

oh my god I love this let's go do this

7:37

one. Now in your own life

7:39

when I encourage you to reflect on is

7:41

what are you using data day. Or.

7:44

What problems are you excited to work on?

7:46

And. I think that such a great way to spend your

7:48

life. What? Are the things you're using Data Day

7:50

that you would like to be more part of? or

7:53

what proms would you want to spend your life on

7:55

and i i i do think i've made really good

7:57

decisions because of that and it's lead mean a path

7:59

where at now my job is to promote

8:01

software products or promote how people can start entrepreneurship

8:03

or make content and figure out how people can

8:05

consume and take action on that content. And those

8:08

are all problems that I've been really excited to

8:10

be doing. Learn personal finance. This is,

8:12

you know, we'll talk about relationships and another brilliant

8:15

advice, but if you can just learn about your

8:17

money better, like such a game changer, you know,

8:19

back in the day, and I still use the

8:21

same spreadsheet, which is assets, liabilities, net worth. And

8:24

then if you can start looking at other

8:26

businesses' P&Ls, and there's a lot

8:28

of companies these days, like Buffer, who share a

8:30

lot of their P&Ls publicly. I think

8:32

Bear Metrics also used to share a lot of the

8:34

finances of these different companies, or you can go to

8:36

indyhackers.com, but just learn about your own

8:38

personal finance and learn about business finance. So I

8:40

went to college for business in undergrad, I didn't

8:43

learn shit there. But starting a

8:45

business, the experience of business, and understanding the

8:47

finances of business really teach you

8:49

that, holy shit, taxes are crazy, so

8:51

how do I minimize that? Maybe you create an LLC. Holy

8:54

shit, my day job is fixed, right? There's

8:56

a limited cap on that, so maybe I

8:58

need to create other ways of optimizing my

9:00

revenue streams. I'm running this business

9:02

and it's not super profitable, well, that's interesting, what's

9:04

really going on there? And so just having a

9:06

deeper understanding of personal finance and business finance is

9:08

something that I definitely did well. And maybe, let's

9:10

separate this talk in things I did that I'm

9:13

glad I fucking did and things that I highly

9:15

regret in business. In business, I'd

9:17

say find someone to hate. I

9:20

know this is, I'm an optimistic, joyful person,

9:22

which is a learned skills, but I definitely

9:24

have frustrations. But I would say the

9:26

hate and anger of Facebook really had a good decade,

9:29

I got a good decade of squeeze out of that

9:31

one. So find someone to hate, let

9:33

your hate motivate. And I reflect

9:35

on the business that I approached in

9:37

my 20s, and I

9:40

wonder, candidly, how did I not give up?

9:42

I was joking earlier this morning about how I

9:45

applied for a job at Yahoo, it was a

9:47

six-figure job, after Facebook, and I remember thinking, I

9:49

just can't do it. Like, one, Yahoo's dumb

9:52

for hiring me, let's just start there, we

9:54

even use Yahoo nowadays. But I just can't

9:56

do it, I'm so angry, and I need

9:58

a chance to show my. that I

10:00

can prove them wrong. And I

10:02

would say in my 30s, especially in my 40s, proving

10:04

myself right. But find an enemy

10:06

to really motivate you. And maybe it's not

10:08

this hate part, but I will tell you

10:11

that fucking got me going in business where

10:13

I was just like, I'm gonna keep going

10:15

until I finally prove them wrong. And

10:17

what you realize in that business experience, because you

10:19

need to have something to motivate you. Like when

10:21

people ask, what motivates you? I was like, myself,

10:23

because I'm fucking angry. You can even hear my

10:25

voice how it brings up a trigger in me.

10:28

And over time you realize that these people

10:30

don't care that you hate them or that

10:32

you motivate them. And over time

10:34

you realize that maybe you wanna be motivated out

10:37

of excitement and optimism. And that's how it will

10:39

shift over time. Or who you're working

10:41

with, the problems you're working on, the things you're

10:43

spending time on. And you will get that shift.

10:45

But find that thing that really is inspiring for

10:47

yourself that you're excited to get up early in

10:49

the morning to check it, you're staying up late

10:51

to working on it, and you're motivated around it.

10:54

Another thing I would say, I don't know

10:56

if it's maybe more of a mix is that I would

10:58

just be intense. I think there's

11:00

times for different intensities where I

11:02

would just be insane on this work. So when we were

11:04

doing Gambit, I kid you not, I was probably working 16

11:06

hour days because a lot of our customers were in Europe,

11:09

and it was awesome. We got $150,000 a day in

11:11

revenue. We

11:13

were doing it at our peak. It was about $15,000

11:15

a day in profit for three people. A

11:18

lot of money. And I was

11:20

good with that intensity. And I think

11:22

the reflection on that business advice is that

11:24

if there's opportunity, sometimes it is time sensitive

11:26

and you have to run with it. And

11:29

there's also a business advice on the

11:31

other side of that about having consistency

11:33

and sustainability in your success. So

11:35

if there's intensity, run with it. And I think

11:37

maybe what I'd reflect on from a business perspective

11:39

is that it's intensity to get the ball rolling

11:42

and then it's sustainability to get the ball winning.

11:44

Another business advice, give gifts. Gifts

11:47

are the cheapest way to get people to like

11:49

you. I did a gift to

11:51

get a customer named Greg Sang. He ran tag.com.

11:54

I don't know if it's still around, but they were

11:56

like the shit back in the day. And I remember

11:58

he was a runner. So I sent him. running

12:00

shoes. Such a stupid ass way

12:02

to like get him to actually pay attention to me,

12:04

but that eventually led him to do a deal which

12:06

ended up making us tens of thousands if not hundreds

12:08

of thousands of dollars from some shoes. So

12:10

I think gift giving either before, during or

12:12

after your interactions with people and really just

12:15

be observant. From employees and teammates which I

12:17

see at AppSumo and what I see from

12:19

almost the world is we just want to

12:21

feel acknowledged and a gift is a cool

12:23

way to acknowledge and really see someone else

12:25

and I think in business it's very undervalued and it

12:27

doesn't have to be expensive. Like if you don't have

12:29

any money then make content as a gift. Make

12:32

a research as a gift. You can do

12:34

things like that but if you have even

12:36

$100 you can send someone parachutes. My

12:38

things about gift giving is you want it

12:40

to be something that they use regularly and

12:43

see regularly. So cups, coffee mugs

12:45

like an ember coffee mug I think is a cool

12:47

idea. It's something unique. I got my buddy

12:49

Lewis House some New Air Jordans they were about a

12:51

G but it was just like wow he's gonna be

12:53

like damn that's a little going for a thousand bucks.

12:55

Like it's just a cool thing to send to someone.

12:58

As well Ollie of Doll. I love Ollie of Doll.

13:00

I go get his book Feel Good Productivity. He was

13:02

so unbelievably helpful advice and just support around a million

13:04

dollar weekend. So I sent him a gift for him

13:06

and his fiance. I sent him a

13:08

cool camera that they can do for date night. Again

13:11

gift giving highly underrated.

13:16

We've got a sponsor. I've got a gift some love too

13:19

and no they didn't even pay for this. I just love

13:21

their product so much and want to give them some love

13:23

and encourage you to check them out. It is LMNT or

13:25

as some people call it Element. It is

13:27

electrolytes. It is salt. I use it almost every

13:29

single day and definitely every single time I am

13:31

cycling you probably have seen these guys on Tim

13:34

Ferriss. You've probably seen it with Lance Armstrong. Noah

13:36

Kagan. Holy. We have

13:39

a free pack with

13:41

free shipping. That's my

13:43

favorite prices at drinklmnt.com/Noah

13:45

Kagan. That's drinklmnt.com/Noah Kagan.

13:48

My favorite flavor is

13:50

raspberry and I hate raspberry. Like

14:01

if you haven't gotten a dollar, $3 million we cannot give

14:03

you a dollar, but I still get excited making a first

14:06

dollar. What I'm learning and noticing about

14:08

business in general is that most people never get the

14:10

dollar, and then when they get the dollar, they're looking

14:12

for a separate dollar, and I'm like, no, just look

14:14

for dollar number two. And so

14:16

how I've shifted my perspective over time is like once

14:18

you get the first dollar and you get the second

14:20

dollar, like stick with these things. That's a powerful one

14:23

that maybe you're not really recognizing, which is get the

14:25

first dollar, and then get a second dollar and a

14:27

third dollar. Don't try to get brand new dollars in

14:29

a separate category. Just keep working around that. Another

14:31

business advice I'm seeing from a lot of other people

14:34

is that they have a day job and they have

14:36

a network and an X skill. They're trying to get

14:38

their startup and their business in Y network and Y

14:40

skill, which is a very hard

14:42

thing to cross over, and we see these

14:44

stories about it, which doesn't mean it's impossible,

14:46

but it's just more challenging. And

14:48

so a lot of people have day jobs and they're like, I wanna

14:51

be a content creator. And it's like, it's the same as your day

14:53

job. It's the same, it's a job. And so

14:55

instead of making it such a big jump from

14:57

totally different industries, can you start smaller on this

14:59

stuff? And if you wanna be in content

15:01

creation or if you wanna build stuff for content creators, this is

15:03

like the exact thing. I wanna build stuff for content creators. Do

15:05

you make content? No. Do you know a lot of

15:07

content creators? No. Okay, that's

15:10

gonna be hard. Doesn't mean you can't do

15:12

it. It's just gonna be a little harder. So how do

15:14

you approach that for yourself in a small way, just

15:17

like getting a few pieces of twigs? One

15:19

of the thoughts I was having was like in my 20s, my

15:22

regret was I was just trying all these businesses

15:24

and in my 40s, I'm saying no a lot

15:26

more. So I'm selling most of my real estate.

15:28

I think it's really thinking about the lifestyle you

15:31

want to live. And in my

15:33

20s, I think it's like, oh, you're supposed to do

15:35

real estate, you're supposed to have a job, you're supposed

15:37

to live these things. And to me, I felt frantic.

15:39

And so I have regrets of how frantic I felt.

15:41

And then it's kind of pulling back from that franticity

15:44

and really dialing in and thinking more

15:47

about what's the life I wanna work backwards from.

15:50

I'll tell you one of the things in business that was the most

15:52

helpful was getting cheated on. I

15:54

was working at Intel and I got cheated on. and

15:58

my mom put her arm around me and she's like, it's gonna be okay.

16:01

And everything ultimately actually is always okay. But

16:04

what that sparked me to do was really just map

16:06

out, like I think I wrote 30, 90, 365, 10.

16:11

And it was just working backwards from where I

16:13

wanted to go. And I still think one of

16:15

the best books of all time is Stephen Covey,

16:17

seven habits of highly effective people. It doesn't say

16:19

successful. And that was a great reminder of

16:21

working backwards from where you wanna go. I think

16:23

I always knew I wanted to be an entrepreneur, make a lot

16:25

of money, live my life away. I just didn't know how I

16:28

was gonna get there. And so actually being a little more concrete

16:30

with that, saying, all right, how do I get $1,000 in a

16:32

year? And I remember by 30,

16:34

I wanted to be a millionaire, which I think I got to

16:36

that. I wanted to have my own house, I did not have

16:38

that. I wanted to have a wife, kids and dog did not

16:40

have that. But at least it gave me somewhere to shoot for.

16:43

So working backwards from some of your goals. You

16:45

know, some of the business advice, I was very

16:47

good at getting focused on something to accomplish, maybe

16:50

to a fault. So Zuckerberg taught me

16:52

about focusing on one goal. And so the good about

16:54

that is I would get, we talked about working backwards,

16:56

I would get obsessed to get to the goal at

16:58

all costs. And then I would kind of

17:00

stop right after I got the goal because I was so

17:02

fucking tired. And I was like burnt of these different areas.

17:04

And so it's great to have one goal, but make it

17:06

a more achievable goal that you can, if you, when you

17:08

hit it, you can sustain that

17:10

for a longer period of time. What

17:12

I learned at Mint was the best marketing is a

17:14

great product. And it was so

17:17

exciting to work on it for myself because I

17:19

loved the problem. And the marketing

17:22

was just easy. You know, Aaron, the

17:24

founder came over two days ago for some tea at my

17:26

house. And he was just like, I've never seen one market

17:28

like you did. And I wonder from time, like if I

17:30

didn't do it in the marketing or I hired someone else,

17:32

like what would have happened for Mint? Would it have been

17:35

where it is? Maybe. And so I do think there's a

17:37

balance. Like if you make a great product and tell no

17:39

one, you know, I think that's the fantasy people trick you

17:41

on. Like, oh, if you make a great video or make

17:43

a great song, you make a great software, you make a

17:45

great book, like people just tell others about it. But

17:48

if no one knows about it, I think that's

17:50

gonna be a lot harder. And so to make

17:52

your marketing easier, find a business and

17:54

find a problem that people are excited about. And it

17:56

makes the marketing fun and it just a lot more

17:58

easier to be effective. One thing about

18:00

the thing about businesses, I started doing

18:03

these conferences and work backwards from the

18:05

customers who have the money. It doesn't mean

18:07

rich, it means people who have the money. And so when

18:09

I was doing my conferences, Community Next, I

18:11

remember the first conference, I went and looked at

18:13

who was sponsoring other conferences. This is the same

18:15

thing I talked about in Million Dollar Weekend, where

18:17

I went and studied other books, I went and

18:19

talked to other authors, I went and looked at

18:21

other covers, I did a lot of testing. And

18:23

so how do you work backwards from things that

18:26

are clearly working or people that are already spending

18:28

money? So I remember hitting up people

18:30

at Yahoo, people at other businesses, and they

18:32

were already saying, like, yeah, I spend money.

18:34

So work backwards from these customers that are already

18:36

spending money. It made it a lot easier

18:38

because I knew they were already saying yes

18:40

to the spends. Another thing in business advice

18:42

that was super helpful is agree on the outcome of success

18:44

of your customer. So what I mean by that is, as

18:47

I was doing these sponsorships, one of the things I'd be

18:49

asking people is like, how do you measure your success? Like

18:51

if this is the best money you spend all year, what

18:53

would make it worth it for you? And it was interesting

18:55

because there was a lot of different things. Like some people

18:58

say, I just want leads, meaning people. So just give me

19:00

15 people to sign up for my service and makes it

19:02

worth it. Other people will be like, I just want exposure.

19:04

Those are great because I didn't care. And

19:06

so be mindful of your customer

19:08

success and align on that. And the same

19:11

thing with people you hire. I'd say another

19:13

piece of business advice, I didn't think I

19:15

did enough of my 20s, is really about

19:17

leadership. Self leadership and

19:19

external leadership. And so self leadership is just making

19:21

sure you're leading in a way for yourself that

19:23

you're proud of. And external leadership is

19:26

how are you hiring people? And so especially if

19:28

you're just getting started, hire a cleaner at your

19:30

house. Really not, yeah, that's leadership.

19:32

Silly, but it's hiring someone, it's agreeing on a money, it's

19:35

making sure they're responsible, it's making sure they follow a checklist,

19:37

it's making sure that you're checking in on them. I

19:40

would say that is a skill I developed definitely more

19:42

in later 30s, as AppSumo got

19:44

started, but something that you can do today,

19:46

you can get an assistant on hiremymom.com or

19:48

on Fiverr or on Freelancer or on Upwork.

19:52

And all of business is a problem that people want

19:54

solved and then finding other people to help you really

19:56

run that business. A lot of these things people

19:58

are trying to make you feel that it's not a problem. It's over complicated,

20:00

I don't think that's the case. So

20:02

yes, work on your leadership skills. One

20:04

of the things I didn't used to do video chat interviews

20:06

with people when I hired them, and I

20:08

remember I did one with a person, I was like, holy shit, I gotta

20:11

do this, because this guy was really creepy and I was scared of him.

20:13

And I was like, shit, I should have hired him. So

20:15

like, damn, do a video interview. I

20:18

would say a good business tip for everyone is just practice

20:20

fucking selling and getting good. And what

20:22

is a sell, it's an ask. Selling,

20:24

it's actually negative connotation these days, but

20:26

everyone's selling you something, and influencers are

20:28

selling you or Amazon affiliate link, or

20:30

someone's selling you their product, or

20:33

someone's trying to sell you on a relationship. And really it's

20:35

an ask. And this is something that I've

20:37

been thinking about, which is how do you just get better

20:39

at asking? Right, and it's chapter two

20:41

in the book, A Million Dollar Weekend, which is

20:43

practicing this. And so asking for a

20:46

sponsor of a conference, asking someone to attend

20:48

a conference. I remember asking someone

20:50

to email out to their audience, to their

20:52

Yahoo Groups newsletter, like, hey, I got this

20:54

conference, can you email it out to other

20:56

VCs? And when people

20:58

say, how do you ask better? It's not even how

21:00

you ask, it's just that you're asking and then you

21:02

practice it. And so I would say in

21:04

your own life, can you practice for a raise? Can you

21:06

practice asking for a discount? Maybe on your bills, maybe on

21:08

a coffee. And the more that you do

21:11

these things right away, the more you realize that it's been

21:13

holding you back, but it's also what's gonna set you free.

21:15

And I got better at it. I

21:18

just kept asking for all these things that now

21:20

I've got to tone down, and I'm asking for

21:22

too much sometimes. So I think

21:24

that was really great. I'd say especially in my

21:26

20s, there

21:28

wasn't as much social media around, but I would

21:30

say what I can see more people doing better

21:32

in business is prioritizing their time in business. If

21:35

you think about your week and you wanna change your

21:37

life in your business, how much time you're actually dedicating?

21:39

Like, look in your calendar and how much time is

21:41

actually allocated around it. And if you go up one

21:44

hour and one Netflix, you can really change

21:46

your life this week, today. And

21:49

that was something that I did really well and

21:51

where I was very motivated to get out of

21:53

a job. And that led me to

21:55

work in the mornings, work on nights, work on

21:57

weekends. And I remember

21:59

distinctly. speaking at Techstars Boston, I

22:01

think it was like their first class, and I

22:03

was talking about mint, but I got

22:05

kind of excited about these Facebook games. And I remember giving

22:07

my speech, and then during my speech, I was like coding

22:09

in the audience. And

22:12

the important thing for you is have somewhere to go,

22:14

have a dream in your business life, have a dream

22:16

that you want to work backwards from. And

22:18

then really, as you're doing your day-to-day, week-to-week

22:20

activities, really think about, okay, what's my opportunity

22:23

cost here? Like if I get this thing

22:25

going, when I get this thing going, like

22:27

I could do that, and then in the

22:29

next literally 30, 50 years of my life,

22:31

I'll have an awesome life, or I can enjoy

22:33

this crappy Netflix show. And

22:36

that was something that highly motivated me because I wanted

22:38

to get out so badly that I was willing to

22:40

swing on all these things. You know, as I

22:43

talk about my business experiences in my 20s, a

22:45

lot of it was close encounters of success, but

22:47

there was just so many great learning moments across

22:49

all this stuff, from conferences to coffee meetings to

22:51

brain pickings. You know, it was like, I pick

22:54

your brain, to blogging, to starting so many things

22:56

now, to how I was starting so many things.

22:58

I was just kind of saying yes to almost

23:00

everything. And if you think about it at a

23:03

high level, one, I feel good about that I

23:05

kind of kept going because I think a lot

23:07

of us, it's easy to want to stop. I

23:10

think if I had to summarize it, it's like in your

23:12

20s or just if you're earlier in your business journey,

23:15

say yes to everything so you

23:17

can say no to what matters. Say yes

23:19

to everything so you can say no to what matters.

23:22

And I would say yes to all this stuff and

23:24

all these people. And then eventually

23:26

over time as you understand yourself and how you want to

23:28

live, you really just start dialing in what really matters. And

23:30

you're like, okay, I'm going to say no to this stuff

23:32

now because I know what matters now. And

23:34

it takes time to get to that level of wisdom. I

23:37

think other business thing I'm seeing, brutally honest, people try to

23:39

do something brand new when they have things that already work.

23:41

And they already have so many things in their network

23:44

and in their zone of influence that they're just not

23:46

leveraging or their skills are not leveraging. Like there was

23:48

a guy who emailed me and it was such a

23:50

cool email. He said, hey,

23:52

I have an email list about

23:54

Porsche, vintage Porsche prices. I was

23:57

like, that is the most niche thing I've ever heard.

24:00

like Miata prices, but no one really cares

24:02

about that. His name is David Whitlock, and

24:04

he said, yeah, you know,

24:06

I've had these Porsche prices, and he

24:08

chose a Freedom number, and I won't share

24:10

his, but then in one day, he just

24:12

shot an email to me. He hit a 1,600 person mailing

24:14

list. I mean, most of you guys can get 1,000 person

24:17

mailing lists over some period of time. Of

24:20

course, people, and he said, hey, I have all this data

24:22

on Porsche prices. Does anyone want to pay for it? It's

24:24

$400 for my database. Just sent it

24:26

out, did a test. He started right away really quickly.

24:29

I don't know if you want me to share his numbers, but it's almost $10,000 from

24:32

one quick test email to a

24:34

very small niche audience. I

24:36

think that's just like such a cool story of, you

24:38

know, you start, you swing, you try, you keep going,

24:40

you start, you swing, you try, you keep going, and

24:43

it really gets you to these amazing places in business.

24:45

I think what I would end again on this is,

24:47

I think we think it's someone else out there that's

24:50

supposed to have these things or someone else in business

24:52

that's better than us, and the reality is they're not.

24:54

They're different than us, and they have skills that we're

24:56

not good at, and we find them to compliment us,

24:58

but we don't have to think that we're not able

25:00

to get to these different places. It may

25:02

not happen immediately. It may not, but

25:04

I promise you, if you stick with the business

25:06

stuff, if you follow a million dollar weekend processor

25:08

and other variations out there, you just keep going,

25:10

like you will get to the spot, I promise.

25:13

I think it's very interesting to work on things you

25:15

just hate. I did

25:17

that a lot. Like we built this better arcade

25:20

site, and I just remember hating my partners. It

25:22

was a sports gambling website, which now is like

25:24

DraftKings, but just like, don't work on things you

25:26

hate. It's too short, but I was like, and

25:30

I spent six months just being afraid, and I

25:32

wish I would have been more confident that hey,

25:34

this is not right. I don't like

25:37

this. I don't like these people, and feeling more confident to

25:39

leave that sooner. The other thing I

25:41

would say, what's interesting about that is that everything

25:43

has two sides. So that business led us to

25:45

build Gambit, which was a payment, which

25:47

then exploded. And then Gambit, even

25:50

though it didn't work out, we were very close

25:52

to then leaving Gambit to starting a Stripe product,

25:54

which Stripe didn't exist. And so

25:56

even though the thing you have you might hate, it's

25:59

teaching you something, and it's really. really leading you to a

26:01

place that I think you can stick with. There's

26:03

a lot of value in business. I think business, there's

26:05

two parts of it. It's finding something people really want

26:08

and then sticking with it for an exceptionally long period

26:10

of time. And I think what most people are getting

26:12

backwards in business is grit and sustaining is taught as

26:14

a virtue and something to do. And

26:16

what happens though is they're sticking with losers too long.

26:19

They're not finding the winner and sticking with it long enough.

26:22

And I think around 30 is

26:25

when AppSumo got started and I

26:27

thank God with all these lessons

26:29

from partners, from marketing, from starting,

26:31

from asking, from a goal,

26:34

from all these different attributes. It

26:36

was like getting AppSumo to 14 years later, which is kind

26:38

of crazy, it's really 14 years. And

26:41

the places you will go. So

26:43

that was a rambling of a bunch of different ideas

26:45

around business for myself. And maybe

26:48

leave it with, why not you? Why

26:51

not you? That

26:55

is a wrap. I hope you loved the episode as much as we

26:57

did making it for you. Remember to

26:59

check out the incredible lifetime deals that

27:01

we've talked about during screenbreak at appsumo.com.

27:03

They're limited edition only. Also

27:05

check out my brand new book, Million Dollar Weekend. You

27:08

guys have already heard about this a ton. I've talked about it a

27:10

ton. But you know in business, they say, what do they say? You

27:12

have to repeat the same thing a thousand times for people to finally

27:14

do it? Yes. Million Dollar

27:16

Weekend, go to milliondollarweekend.com. Go check it out.

27:19

Next text a friend you love them. Finally a couple of shout

27:21

outs to the amazing team who helped make this happen. Thanks

27:24

to Jason at podcasttech.com for

27:27

doing all the magic on these shows. Thank you

27:29

to Jeremy, Cam, Sylvie, Jay, Diego and Memo from

27:31

the Dorking for all the magic y'all do. Have

27:35

a burrito day. What's

27:37

your favorite? Asian Fish.

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