0:00

And welcome to episode six of the Last

0:02

Sell . I'm Kevin Hill , your co-host

0:04

up here , along with Richie Daigle

0:07

, as always as we talk

0:09

to industry leaders about sells

0:12

, and today we have a very special guest for

0:14

you . It is none other than Ryan

0:16

Sullivan . And Richie

0:19

, tell me a little bit about Ryan . You used to work with

0:21

Ryan , right .

0:22

I did . I did Ryan . He

0:24

hired me when I was at Tide , so

0:27

he was my boss and , yeah

0:29

, so Ryan is a poker player

0:32

. He's very strategic in nature

0:34

, very thoughtful

0:37

when it comes to sales and

0:39

, yeah , this is a great episode . I

0:41

think his specialty is startups

0:44

and helping companies

0:46

scale and get the snowball

0:49

rolling , so to speak , and

0:51

you see , all kinds of really interesting

0:53

stories come out of the startup world . And

0:56

boy did he have some interesting stories to

0:59

share in this episode .

1:01

He did this episode . It did you know ? It's that startup sales

1:03

process going from no

1:06

processes or procedures , or

1:08

sometimes not even a crm , to

1:11

something that is is grounded

1:14

and scalable , and uh , it's it's

1:16

interesting journey as you go through that and

1:18

we relate it as much as we can

1:20

back to card playing , because

1:22

it's all strategy and

1:25

strategy is strategy is strategy , whether

1:27

um it's business strategy

1:29

, chord strategy , chess

1:31

strategy , um baseball

1:34

pitching strategy , it doesn't really matter , it's

1:36

all a game of cabin pounds it

1:38

is and it's strategy in

1:40

the midst of a mess is

1:43

a lot of times startup

1:45

and poker for that matter .

1:46

You can have a poker table where everyone's

1:48

like 7-2 and I'm all in , what

1:51

are you going to do about it ? And it's just chaos

1:53

. And there's

1:56

a messiness and a chaotic nature

1:58

to the startup world as well , where you have a great

2:00

product and you don't understand

2:02

why everybody isn't buying it immediately

2:04

. Great product and you don't understand

2:07

why everybody isn't buying it immediately . And

2:12

you're trying to figure out how to qualify people and how to build pipelines

2:14

and how to build a go-to-market strategy and all these things .

2:16

And ICP is a big big thing for today too . Building

2:18

your ICP

2:21

, or ideal customer profile , and

2:23

some of the dangers of not doing that

2:25

.

2:26

And how to gently tell somebody

2:29

that let's be all things to all

2:31

people and why that's a bad idea

2:33

Ninety nine percent of the time . You know it's

2:35

it's . There's a lot

2:37

of interesting things that come out of the startup land

2:39

as well as out of poker , and the

2:41

stories Ryan had to share were were

2:43

, uh fantastic , and I think some

2:46

of the , the directions that he took I

2:48

didn't see coming , you know so

2:51

it was definitely . I think there's gonna be some

2:53

curveballs that uh catch people off

2:55

guard a little bit in this one yeah

2:57

, so and and let's uh , you

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. But with that said , without

3:39

any further ado , let's go straight

3:42

to the interview let's get into it for

3:44

our listeners who are joining here

3:46

.

3:47

Uh , we have ryan sullivan on

3:49

today . Uh , who

3:51

has quite the the extensive

3:54

career in sales , and ryan , um , yeah

3:57

, maybe a quick introduction for people

3:59

who don't know you like , who are you , what do you

4:01

do , and um , and

4:03

we can go from there yeah , so

4:05

my name is ryan sullivan .

4:07

I live in boston , um , so

4:10

I've been a founder twice

4:12

. Now I'm currently running

4:15

a consulting firm focused on early

4:17

stage supply chain tech companies and

4:20

trying to leverage the experience I not

4:22

only have as a founder but

4:24

as a three-time head of

4:26

sales to basically

4:28

distill down what's great about

4:30

how founders sell , which often is

4:32

not best practice oriented . It's

4:35

through domain expertise

4:37

and excitement and the fact that

4:39

people know they have the juice to make

4:42

things happen and distilling that down

4:44

into processes for companies that

4:46

are hoping to scale up . So

4:48

I was responsible for

4:51

SMB and mid-market sales

4:53

at Cubix on a 10x

4:55

four-year run , and then I

4:57

was responsible for sales and

4:59

go-to-market at Tive through a 6x

5:03

18 months . So just trying to sort of

5:05

boil that down and leverage that framework

5:07

to help companies scale up in

5:10

a time where funding and

5:13

true revenue is

5:16

much more important to investors than it

5:18

may have been previously , it

5:21

really is important right now , especially in this environment

5:23

.

5:23

This VC funding is

5:26

sales customers

5:28

revenue . It's

5:34

much more important than it was a couple of years ago . I mean

5:36

, it's always important , but

5:39

now everyone's talking about profitability

5:41

, about growth as

5:43

well . But getting

5:46

customers in the door is

5:48

not always about building the tech . It's

5:50

about selling the tech now .

5:52

Yeah , absolutely , and a

5:55

lot of the people I'm talking to now . Having

5:58

been a founder and , Kevin , I know you have as well

6:00

when I thought

6:02

about the venture landscape

6:05

over the last decade

6:07

, like after some

6:09

sort of seed funding , pre-seed funding

6:11

, it's like get to a million ARR

6:13

for a software company and then you think you

6:15

should be able to raise a Series A , and

6:18

what I'm finding is that's not exactly

6:21

true in today's market . Some

6:23

of it is because they were overfunded in

6:25

a seed round and some of it just

6:28

is because , since

6:31

there's been less funding , there's

6:33

a lot more options for investors

6:36

. That's really one

6:38

half of what the business is focused on . The

6:43

other half is just I worked at Tive for two

6:45

years and when I got there they

6:48

had a lot of infrastructure set up

6:50

already , so I didn't have to

6:52

spend the first six months like trying

6:55

to build this baseline framework . It existed

6:57

and allowed me to get to selling

7:00

and revenue generation

7:02

more quickly and

7:05

revenue generation more quickly . So I think having some

7:08

sort of fractional help for companies in the early stages make it so when

7:10

you raise the big bag and you get the Series

7:12

A , you don't hire a super expensive

7:14

head of sales that takes six months before

7:17

they're able to

7:20

really start getting to value adding , Adding

7:22

value . Excuse me .

7:25

Yeah , you can't really afford it in this adding adding value , excuse

7:27

me , yeah , you can't really afford it in this market though

7:30

this market , you have to be up and running and and selling to

7:32

to be able to , to raise , raise your next round

7:34

. So I think investors are

7:36

hyper-focused on on that part

7:38

of the business right True sales growth , true

7:41

business fundamentals , I suppose .

7:44

Yeah , and I mean I think like the industry element

7:46

is just another complexity . Like Dan

7:49

Clark so the founder of Cubix , who really taught

7:51

me what I know about transportation as

7:53

I was learning it , I'd be like this does

7:55

not make sense , that this is how it

7:58

operates , and he would always say transportation

8:01

is the oldest industry in the

8:03

world , say

8:07

transportation is the oldest industry in the world and the processes were

8:09

built by C students , because in the 50s , 60s , 70s there's

8:11

no supply chain degrees in

8:13

college . People come back from the military

8:16

or

8:18

they didn't go to college and this is the

8:20

path that they chose . So

8:22

it's just , those

8:25

are his words , not mine . But you

8:27

know it does add a

8:29

level of complexity where you see people

8:31

come in from other industries and

8:33

it's hard to even understand some of the fragmentation

8:36

. It's

8:42

hard to understand that a bill of the

8:44

carrier versus broker versus forwarder

8:46

versus asset based broker , value

8:49

propositions and differences . So

8:52

you know , I think that that understanding

8:55

is something that is really

8:57

important from a go to market standpoint and

8:59

I've seen a lot of failed attempts of you

9:02

know more generalists trying to come into the market and

9:04

or into the supply chain tech market

9:06

and be successful .

9:08

It makes me think of you know

9:10

. Tim Ferriss put something on

9:12

LinkedIn I think , two days ago . I'm just going

9:14

to read it . He said refine

9:16

rules and processes before adding people

9:19

. Using people to leverage

9:21

a refined process multiplies

9:23

production , but using people

9:25

as a solution to a poor process

9:28

multiplies problems . And

9:31

it kind of speaks to the importance

9:33

of really

9:35

refining and building good processes

9:38

, whether that's a tech stack , whether that's a

9:40

market strategy , whether whatever

9:42

it is like , if you can nail that early

9:45

on , then when you're adding people you're

9:47

adding leverage Versus

9:49

if you're just trying to use

9:51

people as a band-aid , things

9:54

just get messier down the road , Switching

9:58

gears a little bit . What

10:00

is your favorite vacation

10:02

spot ? If Ryan Sullivan is going to go

10:05

on one last vacation , where is he going ?

10:08

I think I would go

10:10

. So I'm going to say France as

10:13

a whole . Paris is my favorite

10:15

city , but I like the culture

10:17

. I was a history major . The French Revolution

10:20

is my favorite war , so

10:22

very interested in that . But both

10:24

times I've been taking the high speed

10:26

train to nice as well , um

10:30

, which is right next to the monte carlo

10:32

, so go over , get a little poker

10:34

. Beautiful beaches , incredible

10:37

food and , you know , really just appreciating

10:40

the , the culture and

10:42

?

10:42

and what's your favorite

10:44

beverage , alcoholic or non-alcoholic

10:46

? If you have one drink that's your

10:48

go-to . What are you sipping on ?

10:52

From an alcoholic perspective , bentwater

10:56

Sluice Juice is a

10:58

New England hazy IPA . Then

11:01

non-alcoholic I would say Grafruit

11:05

Perrier seltzer

11:07

with your pinky up . I'm

11:10

a volume drinker of seltzer

11:13

, all right .

11:16

This seems to be a trend . We had Scott

11:19

Leeson recently and he also talked

11:21

about being addicted to bubble water . I

11:24

also share this addiction . Maybe this runs

11:26

across salespeople in general , but

11:29

so we're in the future

11:31

. You have hair again , but

11:33

you also have a lot of wrinkles . And you're

11:36

in France . You've just taken a high-speed

11:38

train down to Nice

11:40

and they have

11:42

some kind of way on the train . They had

11:44

this slush juice just pouring , like

11:47

everybody was drinking it in

11:49

the entire train . They're walking all

11:51

over the place . It was at the casino , at the Monte

11:53

Carlo as well . They

11:56

had the grapefruit bubble water . Everybody's

11:58

got their pinky out . You as well . Here

12:01

you are and you're older and you realize

12:04

. Well

12:07

, and here you are and you're older and you realize I am completely done

12:09

working . I am retired , I've made my money , I'm enjoying retirement . Now

12:11

, if you look back on your career

12:13

, what's the last thing that you sold ?

12:19

So I mean

12:21

my hope would be that it's a

12:24

company . You

12:39

know , I think for me , having been a part of two exits , you know the idea , like the stage I usually come

12:41

in is from a building standpoint , right . So that's like the optimization , many of the processes

12:43

, the hiring profiles , the

12:45

systems , they , they don't exist . So

12:48

to me , the most rewarding

12:50

part , parts

12:52

of what it is that I do is

12:54

, you know

12:57

, helping to build a company that is so

12:59

exciting that another company

13:01

would see the value in purchasing

13:03

it , and then seeing the

13:05

trajectory and growth

13:07

of those that I've worked

13:09

with . I mean , I think for me , like my

13:12

coaching tree is like

13:14

what is

13:16

most rewarding to me about you

13:18

know what it is that I do and what

13:20

I've done , so I would hope it's

13:23

a company .

13:31

And yeah , nice .

13:32

What if ?

13:33

it wasn't a company .

13:34

If it wasn't a company , then

13:36

I would hope that

13:39

Maybe

13:42

the company was the second to last sell Company .

13:44

Well , so then it would be a complicated

13:47

multi-stakeholder

13:49

enterprise

13:52

software deal

13:55

. I mean , I think from a sales

13:57

standpoint , the most enjoying deals

13:59

I've been a part of were

14:02

at Tive , a

14:07

part of were at Tive , and it really was just because

14:09

you know selling transportation management systems so many different

14:11

departments are involved . You

14:14

know it's complicated , it's

14:16

more on the expensive side , so there's more of a need

14:18

to justify business value and

14:21

you know when it works . It

14:24

was the largest tangible

14:26

ROI generator of any

14:28

of the things I've been a part of selling .

14:33

Nice .

14:33

Good answer .

14:34

Good , good answer . So if

14:36

we go back in time , right

14:39

, so this is your last sale , the

14:41

fictitious , what could be your

14:43

last sale ? Right , and I love the idea

14:45

of selling a company , but

14:48

if we back up , what was the first sale

14:50

that you've made ?

14:52

Yeah . So I

14:55

mean , like many people in sales , I was

14:57

a server and worked in restaurants as a hustler

14:59

and I also sold cell

15:01

phones and so

15:04

I'm going to skip the server side

15:06

of things , I'm not going to count that . So

15:08

my first sale I worked at an authorized

15:10

retailer at Verizon , and

15:14

my first sale was an upgrade

15:16

of a family of

15:18

three's cell phones . And

15:27

I just remember when I started looking at this leaderboard like how are people doing seven

15:29

, eight , nine , ten upgrades and new lines per day ? Like I just did

15:31

my first one . I'm all excited about it . I upgraded

15:34

, you know , three people's cell phone

15:36

to the iPhone 4 , if

15:38

that tells you anything about how fast

15:40

Apple innovates and how long ago this was . But

15:44

like that's really when I

15:46

started to feel like I understood sales

15:49

because this job was

15:51

at there was four locations

15:54

in the Hudson Valley , new York . It was

15:56

primarily in malls , it

15:59

like kiosks in malls and I just

16:01

that's where sort of the server

16:03

experience came together with

16:06

the cell phone experience to understand

16:08

that you can't just be order taking , like

16:10

if you are not asking questions and you're

16:12

allowing someone to , you know

16:14

, come to you as the expert

16:16

and tell you exactly what they need , especially

16:19

in this time where we didn't have the level of

16:21

access to information that we may

16:23

now that it was nearly

16:25

impossible to be successful

16:27

if you weren't willing to ask the questions

16:30

and go deep enough

16:32

to make a recommendation

16:34

, versus to just follow what your

16:36

prospect is outlining . So that

16:39

was my first sale and that was definitely

16:41

a lesson sort of that stuck with me

16:44

over time .

16:47

And it was a lesson of really

16:51

doing discovery right , of really

16:53

probing down and being

16:56

more of a consultative

16:58

cell than your

17:00

mechanical cell of what

17:02

typically you

17:04

know .

17:04

In a position like that you'd be expected to yeah

17:08

, well , I mean , there was a lot of elements

17:10

of it so like . So , yes , that's true

17:12

, but for example , our compensation

17:14

. We got paid like nothing on

17:17

iphone . So we if you ever went into

17:19

a verizon store and they're trying to talk you out of an

17:21

ip to get the Samsung

17:23

Galaxy or whatever it was Like

17:28

, we got paid tremendously more on that . So I was excited about my first

17:30

iPhone upgrade but

17:32

it was like maybe a fifth of

17:34

what I would have been paid should it have

17:36

been an Android device . And

17:39

you know , over time I

17:41

started to realize that , like people

17:45

didn't know what it was

17:47

they wanted . They knew Apple was

17:49

cool , their friends had iPhones , but

17:51

there was no real reason outside

17:54

of that that that's what they were coming in and saying they wanted

17:56

to buy . So you know , if I

17:58

was able to understand

18:00

not only their technical footprint like

18:02

what do you want to do with it , as

18:05

well as what it is you like to do from

18:07

a general enjoyment standpoint

18:09

, then I couldn't make a recommendation

18:12

to buy something that was not , you know

18:14

, the flavor of the week or

18:17

kind of the thing that they've done a great

18:19

job marketing to make cool .

18:21

It's not all that dissimilar from when

18:24

you're working in a restaurant , though , right , because I mean

18:26

I worked in restaurants too , and bars , and

18:28

I'm sure the people that

18:30

know what they want . They come in and

18:32

all you do is you take their order and it's really easy

18:34

to read that person hey , they're a regular

18:37

or they're just straight and to

18:39

the point . There's a lot of people that walk

18:41

in what do you recommend

18:43

? What's good here ? I don't like they're

18:46

looking to you for some sort of direction on

18:48

the menu or through a wine list

18:50

or through , you know , just building

18:52

a whole dining experience , and

18:55

I think you learn a lot in the restaurant world of like

18:57

how to ask some basic discovery

18:59

questions . What do you like , like , what are the things

19:02

that excite you ? You can

19:04

build an experience . That

19:07

skill set is

19:10

massively important in

19:12

sales . It sounds like you just

19:14

drugged . I would imagine you would have been a good

19:16

server in the restaurant

19:18

world with offering good recommendations

19:21

, asking some discovery questions

19:23

and building a good experience , and you just drug , drug

19:25

that skill set along with you yeah

19:28

, yeah , I mean , but I think , like I

19:30

think that's true , but I think in the moment , at

19:33

22 years old , I

19:37

agree with you , it's very obvious that sort

19:39

of translation .

19:41

But at 22 , like I don't know

19:43

that , like it

19:45

, it took me time , I think , to synthesize

19:47

and sort of digest that and

19:51

I really don't think it's very different from the

19:54

world that I'm in now . But

19:59

you know , I

20:01

love both and I'm biased because

20:03

I did both of them . I love hiring

20:05

people with those backgrounds because

20:07

I think in either

20:10

scenario you really need to be

20:12

able to hustle , you need to understand

20:15

uh personas and

20:17

build rapport , and

20:19

you know you need to give

20:21

uh an experience that you know

20:23

you need to give an experience that is painless , relatively

20:26

painless , and enjoyable for for

20:28

the prospect and operate with urgency .

20:35

So I

20:37

think that skill set translates to anything in business development . And go to market . I agree

20:39

with that too . I went to tables for two , three years and

20:42

you learn a lot of skills , a

20:44

lot of people skills , as

20:47

you outlined . It really is . So

20:53

. We were talking about your first sell at Verizon

20:55

. What was the sell you're most proud of ?

20:59

So the sale that I'm most proud

21:01

of it

21:04

is also at Verizon . Now

21:07

, this was an authorized retailer . This wasn't Verizon

21:09

proper , it was

21:11

100% commission rule and

21:14

they had these like four stores

21:16

in malls that were in

21:18

my territory and

21:21

so I'd been there for

21:23

about six months . I had just started doing . Well

21:25

, somebody

21:27

told me you could sell B2B deals . I

21:29

was like why doesn't

21:31

anyone do it ? They're like well , it's 100%

21:33

commission . People come

21:36

into the stores , you get inbound traffic . I

21:39

was like all right , well , I'm

21:42

not afraid to go knock on doors . So I

21:44

sort of leveraged my contacts

21:48

and went

21:50

and knocked on doors and what ? This

21:53

month it was February , in

21:56

the teens , 20 teens somewhere they

21:59

ran their first contest they'd ever run and

22:02

and it was , if you , the

22:05

highest revenue in the company nationally

22:07

got a cruise with a plus one

22:09

for a week with

22:11

all expenses paid . So

22:13

I basically kind

22:16

of accidentally , went and sold the largest deal

22:18

in New York state history to

22:20

limousine company , which

22:22

was about 500 new

22:24

lines of service . It

22:28

wasn't the biggest in terms of revenue

22:30

that I've done , but it was the biggest in terms of

22:32

impact

22:35

on me and the relative price

22:37

point to what the average deal

22:40

deal size was so it was like four

22:42

hundred thousand dollar deal . So I won the cruise . I

22:44

brought my buddy and

22:47

I met my wife on a bar crawl

22:49

on the second day of that cruise and

22:51

he met her best friend

22:53

and I now have

22:55

two children . We both have two children

22:57

, uh , with our , with

23:00

the wives that we met on that cruise

23:02

. That was

23:05

the biggest one for me . If

23:07

I count my bar bill from that

23:09

cruise , maybe

23:13

it was the biggest deal ever . Have

23:15

you seen Titanic ? I

23:22

was the bald jack but , I made it .

23:27

When you got in front of the ship was all over the ship arms out all over it .

23:29

Yep what I'm hearing from this . My

23:31

takeaway is knock on doors

23:34

, because you never know what's going to

23:36

be on the other side well

23:39

, as

23:41

far as I know , people still weren't doing it , like

23:43

after I had done that .

23:45

Uh , they did end the contest because

23:47

myself and the buddy that I brought that also

23:49

worked there . Uh , I saw

23:51

the owner at a wedding a few months ago

23:54

and he said hey , thanks for teaching

23:56

us the lesson that we need to give different

23:59

prizes for a contest because we had

24:01

two of our top performers leave basically

24:03

directly , uh , directly

24:05

after that . But I

24:07

think it's more testament to the way things are done

24:09

, doesn't mean they are the way things

24:12

should be done , like why

24:15

didn't other people do that ? Was it because

24:17

they couldn't ? No , it's

24:19

because they

24:21

likely wanted to get something different

24:23

out of the job . They , you

24:26

know , probably like that they didn't have to prospect

24:28

. You know that they could make money

24:31

on inbound traffic . But I

24:33

think you know working at

24:35

startups in general and

24:37

I know you're good at this from experience , richie

24:40

is we

24:42

should be questioning the current state and

24:44

how things are done , and there's a time and a place

24:46

to sort of get on board and execute . But

24:49

there's also organizations

24:52

should be happy to have people

24:54

questioning the current state and

24:56

trying to find ways to be

24:59

more successful within those parameters .

25:02

For sure . And that kind of

25:04

gets back to our last episode with

25:07

Amber Diver talking about imposter syndrome and

25:09

people who get comfortable in

25:11

their routine . And when they get

25:14

out of the routine there is a level of

25:16

discomfort , whether it's learning

25:18

new skills , questioning whether

25:20

they're properly

25:22

equipped for whatever new position they're in

25:25

. But that discomfort of breaking

25:27

out of a routine is a sign of growth

25:29

and in your

25:31

instance I mean this is growth . I

25:33

mean it was very evident growth . You got

25:36

out of the normal routine of everyone just

25:38

sits in a store and waits for inbound , decided

25:41

, hey , can I knock on a door ? We can

25:43

go B2B , that's allowed

25:45

, that's cool . Why

25:47

aren't we doing this ? And then you

25:51

just attack that head on

25:53

. So I think that's

25:55

where growth happens . I

26:01

think if you're just in a routine , then your expectation should be

26:03

that things are going to stay the same .

26:04

Yeah , and everyone has imposter syndrome , like

26:06

. I think one of the things that's like helped me

26:09

to build confidence is

26:11

my last three roles have been working with

26:13

first time founders and

26:15

it's easy to look at a founder or

26:17

CEO and be like , well , they should know

26:19

this , you know , look how high

26:22

they are on the org chart , they should know all this

26:24

stuff . But for many

26:26

people , every day is the biggest

26:28

team , the first time they're dealing with

26:30

a challenge , the first time they're raising

26:33

. So once you understand

26:35

that nobody has all the

26:37

answers and everybody's sort of just trying to do

26:39

their best within what

26:41

they know , I

26:43

think it does a lot for confidence to say

26:45

because you don't feel like the only person that feels

26:47

like that .

26:49

Yeah , in my mind there's

26:51

the old , the old story about the

26:53

emperor that has no clothes . I

27:00

think sometimes you feel a little embarrassed and exposed , like I got no clothes on , you know . And then

27:03

when the realization occurs to you that nobody has

27:05

any clothes on and we're all a little embarrassed , then

27:08

it takes a little bit of the sting away . So

27:11

it kind of goes back to what you're saying

27:13

there .

27:14

So if we go on , we're all making it up as we go .

27:17

Yeah , all right .

27:19

Yeah .

27:20

What is the sale that you are

27:22

least proud of or

27:25

possibly embarrassed about ? Was there ever a

27:27

sale that you closed and

27:29

then you thought back oh

27:31

man , what have I done ? Has

27:34

that ever occurred in your

27:36

career before ?

27:38

I have a really good one that I didn't close

27:40

. That's very embarrassing . I have a really

27:42

good one that I didn't close

27:44

. That's very embarrassing . So , selling transportation

27:47

management systems , we had an onsite

27:49

in like Iowa

27:52

or somewhere that , like you , couldn't really

27:54

get to , so

27:58

we had to fly into a major city and drive hours to get there . So we go to this meeting . It

28:01

was supposed to be like 3

28:03

to 6 and it goes like 3

28:06

to 7.30 and we

28:08

had their leadership team in there . It went so well

28:10

. So at the end we're like , hey , we're going to go grab

28:13

a bite . Do you want to come to

28:15

the CEO ? And he's like , no , no , I can't . This

28:17

is the place you have to go to . It's 20 minutes

28:19

away . So we go . So

28:22

what do salespeople do when they leave a

28:24

customer meeting ?

28:27

They're going to blow out some steam , yeah .

28:31

I mean you have to drink .

28:33

You talk about how the meeting went

28:35

. You

28:38

know , and so I was an early on

28:40

manager . I was there with a sales

28:44

engineer and implementation person

28:46

. So we're sitting at this bar and we're talking making

28:49

fun of like picking fun at

28:51

transportation that you needed

28:53

a TMS because you know this guy was ancient

28:55

or you know somebody's

29:11

funny hair . And so I get up from the bar , I walk to the bathroom and

29:13

as I walk to the bathroom I see the back of hair that looks

29:15

like the hair of

29:17

the person that was in the meeting that gave

29:20

us this recommendation to go to this place

29:22

and then declined us . So

29:25

I walked to the bathroom and he's facing

29:28

away from me and I walk back

29:30

and it's him and

29:32

like I try and make eye contact with him

29:34

, no luck . So

29:37

I never heard from that prospect ever again

29:39

. And if you've , uh , richie

29:42

, I don't know that we've been on any onsites

29:44

together , but those that have

29:46

been on my teams know that I now have

29:48

a very , very , very strict

29:50

rule as to . Usually

29:52

you get out of the elevator and the sales guy's

29:55

like hey , how do you think that went ? I'm like

29:57

, nope , we're not , let's

29:59

get in the Uber and talk about

30:01

it . So it was a

30:03

strong reminder that , like you

30:06

know one , you're

30:09

not done . You're not done selling until

30:11

you get an order , and also

30:14

that like just a testament

30:16

to why you know the gossip

30:20

, especially in a public scenario

30:22

, you know is

30:24

frowned upon . So it was very , very embarrassing

30:27

. I wrote handwritten

30:29

letters . I probably

30:32

called them like 25

30:35

times after that

30:37

because it was like we're going forward

30:39

, like let's well , this

30:42

is great , let's schedule the kickoff for next week

30:45

. It would have been in the top 10%

30:49

in deals the company had . It was

30:51

a horrible mistake , but

30:54

all you can do is learn

30:56

from scenarios like that .

30:58

Do you think he overheard you ?

31:00

Yeah , in my opinion , there's no way based on don't ? In my opinion

31:02

, there's no way . Based on

31:04

how the meeting went , there's no

31:07

way that he didn't . And the

31:09

way the restaurant was

31:11

constructed , like I

31:13

mean , this wall behind me is probably 10

31:16

feet . It the . It was a long

31:18

, skinny restaurant , so we were at a bar like

31:20

this and he basically had to walk within

31:23

15 feet of us in

31:25

order to get to his table . So

31:28

yeah , based on how the meeting went , I

31:30

don't think he had to have hurt

31:32

us .

31:33

Do you think it was on purpose ? Do you think that

31:35

he recommended this restaurant , then

31:38

declined your invitation , but

31:40

decided to go anyways ? Just to

31:43

purposefully lend an

31:45

ear to what you all would be saying , I

31:47

mean .

31:49

I don't know . I've spent a lot of time in

31:51

my life thinking about why

31:53

and how this happened , because the

31:55

whole thing is very strange , like

31:57

who recommends a restaurant to somebody , doesn't

31:59

tell them they're going there and

32:01

then declines an invite and still

32:04

goes there . So I

32:06

don't know . Maybe

32:11

that's a smart way to do due diligence that buyers

32:13

should start actively doing . Like

32:15

, the next time that I'm part of buying software

32:18

for a company and we have an on-site

32:20

, maybe I'll try the same tactic to see if they talk

32:22

about my shiny bald head or

32:25

my wrinkly forehead Was it a mullet ? It

32:27

was like a mullet with a bald top

32:29

. It was hysterically funny

32:31

hair . It was genuine . It was like

32:34

just the back mullet

32:36

, but you still had the shine on top

32:38

, so it was like the best of both worlds .

32:43

That is the elusive skirted eggshell and the various

32:45

types of mullets that are out there . There's

32:47

a whole website , I think , that classifies different

32:50

ones .

32:50

What did ?

32:51

you call it Skirted the

32:53

skirted eggshell . Oh , I

32:55

like that .

32:56

I think I could grow one , you

32:58

should .

33:00

You should .

33:01

You'll never forget your mistake if

33:03

you grow that yeah

33:05

.

33:05

Well , it's like I feel like with

33:07

a , as a bald guy , you

33:09

pay more attention to people's hair than anybody else

33:12

. Like I'll be walking with my wife

33:14

and we'll be walking in boston and I'm

33:16

like when we walk past

33:18

someone and she's like , who are , are you , are you

33:20

checking that girl out ? I'm like no

33:22

, did you see the hair on that guy ? So

33:25

I do think that we're just , you know , as

33:27

the Baldies , I think we're more sensitive to people's

33:29

hair . But if we don't have nice things to say

33:32

, we should probably just keep

33:34

them to ourself .

33:36

What was the funniest

33:38

sale ? So was there a sale

33:40

that the

33:42

circumstances were just hilarious

33:45

. Couldn't believe what was happening . Things

33:48

happen in sales . You never know what's going to

33:50

happen in sales . It's always interesting , but is

33:52

there anything that sticks out to you as particularly

33:55

funny experience in sales ?

33:58

Yeah , so early

34:00

in my career I

34:03

was selling email marketing

34:05

software and

34:08

it was super high volume . It

34:13

was primarily inbound leads but they

34:16

were in moderate quality

34:18

in the expectation we were making . Like 80

34:20

to 150 calls

34:23

per day . Somebody

34:29

on my team gets A lot of these are one

34:31

person businesses If

34:34

I have a catering company

34:36

or from a real estate agent or whatever

34:38

. It wasn't uncommon for there to be personal

34:41

email addresses , stuff like that . So this

34:43

person on my team calls an

34:46

inbound lead and basically says like

34:48

hey , my

34:50

name is blank . I'm

34:56

calling with this company reaching out because you filled out a form and you

34:58

know I wanted to follow up with you and see how I could help . And the person

35:01

must have

35:03

been well

35:06

, they were putting like advertisements

35:09

on Craigslist seeking

35:11

intimate relationships

35:13

and they didn't

35:15

listen to the person

35:18

. All they heard is like you

35:20

filled something out on the internet , how can I help

35:22

? And then this man

35:24

went into excruciating

35:28

detail as to what he's looking

35:30

for from an intimate partner and

35:32

the salesperson who

35:35

, like , was

35:37

hysterical because he didn't laugh . He

35:39

just kept asking questions

35:41

, like , but not , they

35:44

were like business-y questions

35:47

. And the guy it was like four minutes

35:49

of this guy just giving

35:51

such horrific details and

35:56

then ultimately like you can hear

35:58

it in his voice when he figures out that

36:01

he's not talking to who he thought

36:03

he was talking to and hung up

36:05

. So that was , that

36:07

was the funniest thing

36:10

. That I've been around and

36:12

probably listened

36:14

to that call hundreds

36:16

of times and

36:27

it used to actually be something that I would even show , like at team meetings . For you know other

36:30

people at other companies I would say , like you know , here's the , here's the importance of

36:32

qualification . You know you never understand

36:34

who is who is on the other

36:37

end of the phone and you

36:39

don't . You can guess what they're interested

36:41

in , but until you ask

36:43

, you know you don't really know .

36:45

And you don't know if you want to know , Did

36:49

that rep ever call him back and

36:51

take another shot at trying to get business , or was

36:53

it like I'm done ? I'm

36:56

off the ride ?

36:59

I'm pretty sure it was done . I don't

37:01

remember , but I don't

37:05

know that there was a big business opportunity there . I

37:07

don't know what the rep was into , so I

37:09

have no idea .

37:11

I'm surprised that the guy didn't

37:13

realize that he wasn't talking to

37:15

who he was talking to and

37:18

he's like oh my bad , I

37:20

thought you were somebody else and went on with my bad . I thought

37:22

you were somebody else and went , went on with the , the sales call

37:24

.

37:26

Yeah , I mean , it was just like At

37:29

some point I think he wasn't getting

37:31

any of the comments or responses

37:33

that he had been hoping

37:35

to get or would have been getting if

37:37

the person was actually calling in regards

37:39

to his Craigslist ad . And yeah , I

37:44

mean that would be . Yeah

37:47

, I don't know , I didn't figure it out , but I

37:49

don't know anybody else that's posting advertisements

37:53

on Craigslist to find a partner .

37:58

Not anymore . No

38:01

no , not in these days .

38:02

That's what ? The glory days of the internet

38:04

. I'm just kidding , not anymore , no no , not in these days

38:06

.

38:06

The glory day , that's what ? The glory days of the internet

38:08

?

38:08

I'm just kidding , yeah 15 glory

38:11

days , yes , 15 years ago . Can

38:14

you just assume that anybody that's calling you saying I saw what you

38:16

submitted on the internet Like yeah , if that's your first go-to

38:19

of a response to

38:21

a number that you don't recognize on your phone

38:23

, yeah , that's a different time

38:26

than today

38:28

.

38:28

Yeah , I mean Craigslist

38:31

should have started Tinder or Matchcom or

38:33

something . It's clear that they had a

38:36

big business around that based on that

38:39

guy .

38:49

Best opportunities that based on , based on that guy , yeah , this opportunities . So

38:51

so , ryan , um , here we go . Two part question , actually . So what cell

38:53

or dill did you learn the most from ? Would

38:56

be one part of it . And

38:58

what poker hand did you learn the most of

39:01

from ?

39:10

So the sale

39:12

that I learned the most from

39:16

was a deal

39:18

to a

39:21

visibility deal to a

39:24

exercise

39:26

bike manufacturer

39:28

and distributor , and

39:31

at that point it

39:33

would have been a deal that like

39:36

doubles the company's revenue , and

39:38

I hadn't .

39:41

I think I might already know the manufacturer of

39:43

these bikes .

39:45

You , you'd be somebody that you'd heard of

39:47

Um and

39:49

we were working with a contact

39:52

in innovation and

39:54

we ran all these

39:56

tests . They were totally qualified

39:59

from a product fit

40:01

and use case standpoint

40:03

. But I

40:06

didn't know what an innovation role

40:08

was . Truly I

40:10

didn't know . I just saw that it

40:12

was like a VP or C level

40:14

title and I was like they must

40:16

have juice . And so

40:19

I went . I mean , I talked about it in the board meeting

40:22

, I went

40:25

through like on paper

40:27

, functionally there was no reason why this deal

40:29

wouldn't happen . But not

40:32

knowing what I didn't know I we

40:35

didn't spend enough time , sort of on the business

40:38

case and it still

40:40

haunts me as like the

40:42

deal that never

40:44

was that like

40:47

we basically got to the end and you

40:51

know it's going to the ceo

40:53

for approval and he

40:55

was basically like that's

40:57

ridiculously expensive and

41:00

we didn't have alignment with stakeholders

41:03

. So you know , for me

41:05

it it taught me a lot about

41:07

. I need to be honest with myself

41:10

because and

41:12

, rich , you may have heard me say this I say alcoholics

41:14

don't get better until they admit they're an

41:16

alcoholic . Capital is and truly

41:18

what their paperwork

41:21

process and business process is to procure

41:23

services . I

41:39

need to at least be honest with myself , because

41:41

you know , if

41:43

I'm honest with myself then I

41:46

do a bunch of research or on

41:48

. You know this role , I know the questions

41:50

to go back to the customer with . So it was

41:52

the most just glaring qualification

41:55

issue that I've had and

41:57

I didn't do myself any favors by

41:59

promoting it internally

42:02

that it was definitely coming

42:04

and it didn't . And

42:07

uh , you know it

42:09

always haunts you when you're like there's

42:12

no reason this shouldn't have worked , other than

42:14

I didn't do the best job .

42:18

I think the deal that never was I like that . I

42:20

mean , I don't like it but I think

42:22

it's something that a lot of salespeople are

42:25

working on and are

42:27

hoping for . In a lot of cases , that

42:29

the deal that never was . I mean , you work

42:31

in a deal , you think you're making

42:34

progress , but it is

42:36

going nowhere fast

42:38

because you haven't done your due

42:40

diligence . You don't know what's really going

42:42

on behind the scenes and

42:44

oftentimes it's nothing is going on

42:47

behind the scenes .

42:48

Right , I mean functionally . Could

42:51

every single company use a CRM

42:53

? Sure , could

42:55

. Could every company use , you

42:58

know , data on their target accounts

43:00

? You know like you provide , kevin , sure

43:03

. But if you

43:05

don't , if we don't know the implication , you

43:09

know why . That is how

43:11

it ranks from a priority standpoint , like

43:13

, truly , who can block it and who can get

43:15

involved ? We're just setting

43:17

ourselves up to spend

43:19

a bunch of time and cycles and

43:21

ultimately not get the result anybody's looking

43:24

for .

43:25

Well , the thing is those situations

43:27

when you're blindsided , right . I think back

43:29

to deals where I know

43:31

this deal is shaky , I

43:33

can see the holes in it , and maybe

43:36

there's not much I can do about the holes other

43:38

than just see them . Right , I'm going to try my best

43:40

to plug them as best I can . But I know that

43:42

the premise is shaky to start

43:44

, or I may see something that I don't

43:46

think this is going to work out at all , but

43:49

I got to follow it through because it might . You

43:51

know , it's a , it's a Hail Mary , it's

43:53

a seven , two offsuit and I've stumbled into

43:56

the turn and I got two pair

43:58

and there's razors all around with flushes

44:00

and straights and everything in front of me and

44:02

it's like I kind of want to see the river

44:05

, to see if I boat up . You know , but it's , you

44:15

know , but it's . You know that you're the odds are against you . But I think it's those moments when

44:17

you're completely blindsided because you thought that all the holes

44:19

were plugged , you thought that your business case was

44:21

rocked , you thought that , um , you're

44:24

on the path to , you're in the final stages

44:27

, you're at the five yard line , and

44:29

then when the ball's ripped out and it all falls

44:31

apart . You're like what just happened

44:33

and you don't even know like it's . It's

44:35

almost traumatic when that , when that kind

44:38

of dark mystery hits you like that , but

44:41

it's only after that . I mean , I think there's a quote

44:43

that says life can only be understood

44:45

looking backwards , but it has to be lived

44:47

going forwards can

44:50

only be understood looking backwards , but it has to be lived going forwards . But it's

44:52

usually weeks or a little bit afterwards when you start looking back through it and

44:54

like , oh my gosh , I missed this , I didn't

44:57

see this coming , there was this hole and

44:59

you start seeing all the gaps and putting the

45:01

pieces together and that learning the

45:04

information that can come from that sort of experience

45:06

can be really rich and meaningful . Yeah

45:10

, I was just trying to summarize . Yeah

45:12

, it makes a lot of sense that that's a something

45:14

you learned a lot from . Hopefully , this poker , this

45:17

poker story , isn't similar where it . It

45:20

was better .

45:22

I mean that . I

45:24

don't have , I

45:27

don't really , I

45:29

don't really . Oh , I do . So , as

45:33

I know , kevin and Richie know . So I used to play poker

45:35

for a living for a period of time and

45:38

I had a hand once

45:41

, and this is when I

45:43

really didn't have much money . I was probably playing for

45:45

$200 or something

45:47

and that $200 meant a lot

45:49

to me and

45:52

I had pocket eights

45:54

. I

45:56

raised preflop . Somebody called flop was

45:58

like eight , six , two . We

46:02

get it all in on the flop . The

46:04

other guy has pocket twos , he

46:06

hits a two on the river and

46:10

it was crushing , soul-crushing

46:13

loss . It's

46:19

like less than 2% chance

46:21

that that should ever happen . And I mean again , this actually goes back

46:23

to exactly what you were just saying , richie

46:33

. Like obviously I was not happy that that happened , but I think after I did , I spent a lot of

46:35

time looking at like how could I have

46:37

avoided this ? And

46:39

the end result was

46:41

there's no way cards

46:44

come out differently , like it's out of my

46:46

, and all I

46:48

did was put

46:50

my money in in a scenario that

46:52

I had 98% likelihood

46:55

to win and , um , you

46:57

know it , it really was just a reminder

47:00

of sort of process

47:02

over results , which you

47:04

know . I'm still going to make that decision every

47:07

single time . I'm still going to be

47:09

disciplined and I'm going to

47:11

be okay losing , so

47:13

long as I'm

47:15

following a methodology that I know

47:18

in the long term

47:20

, yields a better result , and that you're

47:23

going to get unlucky sometimes , like there's variance

47:25

in everything we do , whether it's

47:27

poker or our relationships or

47:30

our jobs . I could make

47:32

a thousand cold calls today and

47:35

have nobody pick up , and

47:38

tomorrow I could make a thousand cold

47:40

calls and have um

47:43

, you know whatever 20

47:45

of people pick up and book meetings . So I

47:47

think , like the point

47:49

I'm trying to make is there's

47:52

variance within percentages that is

47:54

solved by how many times you put yourself

47:56

in that opportunity . Like , if you have

47:58

a 33% conversion rate

48:00

and you run three deals , you might

48:02

get none , but if you run 300

48:05

deals , it should be

48:07

a hundredish at the

48:09

end . So I think that was really

48:11

the big learning experience for me

48:13

in that end .

48:15

And I think that's a very important learning

48:18

experience or lesson learned

48:20

is that you're talking

48:22

about the 98% chance to win

48:24

. You got beat . It's

48:26

a bad beat .

48:39

You got beat .

48:39

It's a bad beat you kick yourself a little bit and then you move on . Right , because

48:42

basically , 98

48:44

out of 100 times you should

48:46

win that hand . So play 98 more meetings and

48:49

don't worry about those those sure things

48:51

. Right , because we , you know , I think we all

48:53

experience this we got this sure thing

48:56

, it's coming in . We're getting in front

48:58

of our bosses , our managers , say

49:00

, hey , this is a sure thing , and it

49:02

just fucking falls apart . Right

49:04

, I mean it . Just it just disintegrates

49:07

, yep . And then if

49:09

you're prospecting , if you're working that process , you're

49:11

going to draw a river card In

49:14

an inside straight . If we're going to go poker

49:16

analogies right , something

49:19

that comes out of the blue falls in your lap

49:21

. You don't expect it , it's good

49:23

luck . But as long as you're doing the activity and

49:25

following a good process that

49:27

you're building over time , it

49:31

all hits out of the end .

49:33

Yep , yeah it's

49:35

, I mean it's .

49:38

So you shouldn't get too down , you shouldn't get too

49:40

up , just work the process and

49:42

enjoy it .

49:43

Yeah , what can I control within

49:46

this process ? And you know what would I

49:48

do the same or what would I do

49:50

differently .

49:53

You know , you make those tweaks and

49:55

you just get better over time .

49:57

Yeah Well , and the other guy shouldn't have done anything

49:59

different either . So , even though he was 2%

50:02

, like the odds that

50:04

I have top set and he has bottom

50:06

set are so minuscule that

50:08

, like so many times , I'm going to be paying

50:10

him off with pocket aces or pocket kings

50:13

, or you know eight , six

50:15

some crazy two pair or something so like

50:17

. Again , just because he was getting

50:19

it in at two percent chance

50:21

to win doesn't mean that

50:23

he should do anything different

50:26

, because the odds

50:28

that I'm actually beating him are

50:30

so low that if we both

50:32

had the hand to replay a thousand times , we

50:35

both do the same thing every

50:37

time and it's actually

50:39

so . That's like kind of the interesting

50:41

thing about it is even

50:45

the guy that got lucky on the river . If

50:48

you know , I have the hand , I have you don't call . But

50:50

most of the time I'm not even going

50:52

to have that and you're just going to scoop the pot and

50:54

you don't need to hit quads on the river .

50:57

Yep , yeah , you know

50:59

, I mean three , twos . I mean that's still a great hand

51:01

, sure yeah , I'm

51:03

calling you .

51:04

If I have three twos , if

51:07

I have pocket twos , and I spike a two and

51:10

Sullivan's pushing , I'm going to say , ryan

51:12

, why are you letting me take your money like this ? And you're saying

51:14

, richie , I'm taking your money

51:16

. That's how it would go down

51:19

just about every single time . It's

51:29

a reminder of how oftentimes we think we're in control of things that

51:31

we're not completely in control of , and

51:34

that's a good reminder to look back at

51:36

what is 100% in your

51:39

control . You know , and yeah , it's

51:42

a good audit practice to run from time to time to remind yourself what is in your control

51:44

and what isn't .

51:44

Yep , I tell you what what's in my control is . I'm

51:46

going to sit down and I'm going to watch

51:49

Rounders again tonight . I

51:51

haven't seen it in three or four years . I'm

51:53

in the mood now .

51:55

Pay him , pays out the man his

51:57

money .

52:00

He beats me fair and square .

52:02

You know what ?

52:04

I am going to go buy a box of Oreos and

52:06

sit there and watch Rounders

52:08

.

52:10

Is there any other way to watch rounders ? I

52:12

don't think so Without a box of Oreos

52:15

.

52:15

I'll invite you to an online poker game too

52:17

. So you can be . You know you're multitasking

52:20

and uh , when , while

52:22

you're in the spirit , you can uh , you

52:24

can fire a little bit and try

52:26

and hit quad twos on somebody . You can fire a little bit and try

52:28

and hit quad twos on somebody , I will .

52:30

I'll just play the river all night .

52:33

There

52:35

you go , ryan . It's been a pleasure , enjoyed

52:37

this conversation .

52:43

And how can people find you ? So

52:47

you can find me on LinkedIn or on my website , ratchetventurescom

52:49

. And no , I really enjoyed this as well . And lastly , I just

52:51

want to promote . This is a pack

52:53

of baseball cards from the 2007

52:56

Lake Einhorn Storm , and

52:58

there may be a

53:00

Richie Daigle rookie in

53:02

here . I have a few and

53:05

waiting on the autographs . If you

53:07

want a Richie Daigle autograph , you also can get one on eBay . It's not mine , it's $14

53:09

. And waiting on the autographs . If you want a Richie Daigle autograph , you also can get

53:11

one on eBay . It's not mine , it's $14

53:13

. But thanks for having me on , guys . This was

53:16

really fun Always

53:18

a pleasure .

53:19

Thanks , Ryan .