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Hi listeners, it's Mashima Kutonina, a

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producer on Masters of Scale. I

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spend a large part of my day

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why I am such a big fan of

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grammarly.com to learn more. That's

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grammarly.com. The

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night of January 19th, of course, is the famous

1:29

inaugural balls. There

1:35

are a bunch of inaugural balls around D.C., and so

1:37

I get my tuxedo on and go to a inaugural

1:39

ball, and

1:42

I get a message,

1:44

probably a Blackberry message, saying go to

1:46

this random address in D.C. and pick up

1:48

a package. That's

1:53

Ian Bassen, lawyer, activist and

1:55

executive director of Protect Democracy.

1:58

Ian is taking us back to January 19th. 19,

2:01

2009, the night before the historic

2:03

inauguration of President Barack Obama. Ian

2:06

is joining the administration as an

2:08

associate White House counsel, his

2:10

job ensuring the ethics and proper

2:12

rules of governance. Basically,

2:15

one of the people who keeps our

2:17

democracy functioning as a democracy. So

2:21

I duck out of the ball. It's raining that night.

2:23

I run across the district in the rain and I

2:25

get to the building. There's

2:28

a doorman who hands me a

2:30

plastic grocery bag bursting at the seams

2:32

with three thick binders, like school binders,

2:34

right? And it's got my name on the outside

2:36

of the bag. This sounds like this

2:38

may be a foreign operation. Totally,

2:41

right? Like, it's like, you're looking for Jason Bourne,

2:43

not me, right? And

2:46

I bring them home that night and open

2:48

these binders to look at what they were. And

2:52

they contained memos going back

2:54

to the Eisenhower administration. That

2:56

White House counsels and chiefs of staff had

2:58

sent White House staff and executive branch officials

3:00

explaining the rules, explaining what

3:03

people were allowed to do and were not allowed

3:05

to do in the performance of their duties. And

3:07

what was striking about it and became so clear

3:09

over the next three years where these binders became

3:11

my Bible was that a lot of these

3:13

rules are not legally binding. They were just

3:16

traditions. They were customs that were passed down

3:18

from administration to administration. And when people in

3:20

the White House had questions about what was

3:22

allowed, I'd consult the binders. And if

3:24

they didn't contain the answer, I called Emmett Flood,

3:26

who did my job for President Bush. And

3:28

if Emmett and I couldn't answer it, we called Beth Nolan, who did

3:30

it for President Clinton. It didn't matter whether

3:33

we were working for a Democratic president

3:35

or Republican president. The rules were consistent

3:37

over decades. The handoff

3:39

sounds kind of crazy, right?

3:41

There's no three-hour sit-down and a walk-through

3:43

and, let me help you understand how

3:45

this works, et cetera. It's

3:47

in the dark and stormy night you're being

3:49

handed a grocery bag full of binders. I

3:52

mean, why aren't these things codified and why

3:54

isn't the process more formalized? So,

3:56

I didn't understand quite why that was the handoff at

3:58

the time. understand that since.

4:01

So I bring these binders in with me on

4:03

noon on January 20th of 2009. And

4:07

then I served for about three years, almost three years. I

4:09

left the fall of 2011. And I

4:12

left the binders for my successor so

4:14

that my successor could use them. Well,

4:16

flash forward to November of 2016, Donald

4:19

Trump was elected. And I was

4:21

concerned about what's going to happen to

4:23

these binders and the incoming political movement

4:25

that has essentially been organized in opposition to

4:27

customs, traditions, norms like that might disregard

4:29

them entirely. And so I reached out

4:31

to the White House Counsel's office at the end of

4:33

the Obama administration. I said, Hey, I

4:35

know that you need to keep a

4:37

copy of those binders because they are

4:39

a presidential record under a federal law.

4:42

There's the Presidential Records Act, but the

4:44

physical copies that you have were mine.

4:46

I brought them into the administration with me. I

4:48

carry them into the building on January 20 2009.

4:51

I'd like them back. But ultimately, they said no. And I was

4:54

told if I wanted them, I could file

4:56

a Freedom of Information Act request for them, which I

4:58

did. And I was recently informed

5:00

by the National Archives that they will process my request

5:02

in 20 years. I all

5:04

of a sudden realized light bulb went off. I

5:07

see why someone might have just taken these in a plastic

5:09

grocery bag and handed them off to the next administration. In

5:14

story of binders in the night

5:16

ish. We don't

5:18

expect decades of roles and guidance for government

5:20

ethics to be passed down in such an

5:22

ad hoc way. It shows

5:25

how heavily our system rests on

5:27

seasoned professionals having a respect for

5:29

democratic norms. But

5:32

the story of the binders is also reassuring.

5:35

It shows how so many people across

5:37

political eras and divides have worked so

5:39

hard to uphold the standards that our

5:41

lawmakers need to follow. And

5:43

it's that preservation and passing line of standards

5:45

that Ian Bassen went on to make his

5:47

life's work. He left the

5:49

White House and drew on his experience

5:52

as an administration lawyer to found an

5:54

organization called Protect Democracy, where, full disclosure,

5:56

I'm a founding board member. The

5:59

mission? You guessed it, to

6:01

protect American democracy. Ian's

6:03

not-for-profit has had a huge impact. And

6:06

unlike most policy and litigation-focused not-for-profits,

6:09

they're also a tech organization, having

6:11

built and launched software called VoteShield,

6:13

which helps secretaries of state ensure

6:16

they're running free and fair elections.

6:19

I want to emphasize here that Masters of

6:21

Scale is not a political show. We

6:24

explore how to scale businesses, and

6:26

that is the focus of this

6:28

episode, massively scaling an organization with

6:31

a specific, important mission. We

6:33

invited Ian on to learn how

6:36

he's built strong partnerships across opposite

6:38

ends of the political spectrum, and

6:40

how he's done it with a

6:42

100% distributed workforce, long before the

6:44

pandemic, work-from-home era began. I'm

6:47

Jeff Berman, your host, and this is

6:49

Masters of Scale. You've

6:53

got to have incredible talent at every position.

6:57

There are fires burning, and you're going out. You've

7:00

got such an idiot. And then, you know, he's

7:02

holding it to me,

7:04

and there are so many easy ways.

7:07

I have no idea what it is. Sorry, he made a mistake.

7:09

I do have the time, I believe. What's

7:11

the time? We're going to have a free bedroom. That's

7:14

just in the afternoon. All 10

7:16

years later, we're going to have a look at how you do

7:18

it. We have a good decision, and then you do it. This

7:24

is Masters of Scale. Will.

7:31

Start the show in a moment after

7:33

word from our premier brand partner, Capital

7:35

On Business. I.

7:38

Wrote down in a piece of paper: What

7:40

are the stance that we have and what

7:43

are the clear, glaring opportunities that we're. Missing.

7:46

That's Aparna Serin, Chief Marketing Officer for

7:48

Capital One Business. Like many

7:50

leaders, she spent her first months in

7:52

her new position asking those big-picture questions.

7:54

Aparna had always been a data junkie,

7:56

so that's where her interest went. thing

8:00

on opportunities that kept glaring at me was

8:03

in a world where marketing has moved so

8:05

much closer to using big

8:07

data and leveraging machine learning, we

8:09

were far away from there. How

8:12

do we scale our marketing engine

8:14

from where it is today? She

8:16

came up with a plan to refocus

8:18

and called the town hall, but the

8:21

response was not what she expected. We'll

8:23

find out why later in the show.

8:25

It's all part of the refocus playbook,

8:27

a special series where Capital One Business

8:29

highlights stories of business owners and leaders

8:31

using one of Reed's theories of entrepreneurship.

8:33

Today's playbook insight, focus on your

8:36

team and your customers. Today,

8:46

I'm in conversation with my

8:48

good friend, Ian Basson. Ian

8:50

is a co-founder and executive director

8:52

at Protect Democracy. It

8:55

is a not-for-profit dedicated to preventing

8:57

America from sliding into authoritarianism. He's

9:00

over 100 staff members with a

9:02

wide range of political views. They

9:05

do things like safeguard free and fair

9:07

elections by tracking voter registration data and

9:10

ensuring there's nothing nefarious at play. They

9:13

provide legal counsel for election workers

9:15

and others being threatened and defamed

9:17

for their nonpartisan patriotic work. Ian

9:20

and I explore how to work

9:22

together to address massive challenges with

9:24

no obvious solutions and how to

9:26

share best practices with your predecessors,

9:28

your successors, and occasionally even your

9:30

competitors. First, let's hear a

9:32

little more from Ian about his three-year stint

9:35

in the White House. The

9:41

thing that was so striking was

9:43

that everyone understands from the president

9:45

on down that we are temporary

9:47

occupants of an office. We hold

9:49

an incredibly precious and valuable public

9:51

trust that we the people, the

9:54

citizens, give to us temporarily only

9:56

on the condition that we will

9:58

exercise it in their best. interests

10:00

on their behalf. And it was part of

10:02

my job to drill that into, you know,

10:04

the minds and the hearts every way that

10:06

everyone operated in the building and in the

10:08

executive branch. And that really did, you

10:11

know, for the most part, transcend

10:13

parties and administrations. There's one

10:15

part of this that I'm really struck by, which is

10:17

it doesn't matter what

10:19

party you all were working together

10:21

to preserve the rule of law and ensure that

10:24

the White House was operating in an ethical manner.

10:26

Is there any prep for this job? Do they give

10:29

you any context for what you're doing? Or do you

10:31

just walk in on day one and say, I guess

10:33

I'm working for the president? So

10:35

a little bit of both. So one

10:37

thing that's kind of staggering, and I

10:39

remember this feeling vividly when we walk

10:41

into the building noon on January 20th

10:44

is the West Wing executive

10:46

office building. The rooms are empty. The

10:48

desks are clean. There are no papers. There's

10:50

a computer there for us and nothing else.

10:53

And this is the seat of the

10:55

most powerful government in human history. And

10:58

you walk in and it's just empty

11:00

for the new group of people. And

11:02

it was just a wild experience to

11:04

realize that every four years there's

11:06

the opportunity to just swap out the old people

11:09

and bring in the new and start afresh and

11:11

a new group of people come in and they

11:13

take the keys and they take over running the

11:15

federal government. It's a remarkable thing that we've been

11:17

able to do in this country for 247 years.

11:21

We've covered the concept of re-founding plenty of

11:23

times on Masters of Scale. Most recently in

11:25

my talk with Reid Hoffman, which you can

11:27

find in our episode feed. It's

11:30

something I'm focused on as the relatively

11:32

new CEO and re-founder of Wait What?

11:34

the company behind this podcast. It

11:37

is not easy. So the idea that

11:39

the federal government goes through a complete

11:41

re-founding every four to eight years is

11:44

mind blowing. And the reason

11:46

it works, at least most of the

11:48

time, is the deep respect for not

11:50

just the office, but the rules and

11:52

conventions that came before. The

11:54

goal of a peaceful transition of power

11:56

speaks to the dance every re-founder must

11:58

perform to make their own. own

12:00

indelible mark on an organization while

12:02

keeping its mission intact. After

12:05

almost three years working in the Obama administration,

12:07

Ian took on a different challenge in 2011. He

12:11

went to the not-for-profit Avoz, which is

12:13

focused on global organizing to protect the

12:15

environment, human rights, and freedom of speech.

12:18

It was here that Ian learned a

12:21

foundational lesson about building a scaled organization

12:23

that can sustain a succession of leaders.

12:26

The thing that was, for me, the most eye-opening was not

12:28

the subsets of the work, which was fascinating and meaningful and

12:30

important. It was how it was done. It

12:33

was led by a management savant in how

12:35

to think about intentional culture

12:37

in a workplace that built the culture

12:39

from the ground up from the beginning

12:41

as the DNA of the organization and

12:44

wove it into everything the organization did,

12:46

how it tested in hiring, how it

12:48

onboarded and trained people to operate within

12:50

the organization, how it injected that culture

12:52

into every team meaning, into every interaction,

12:55

so that ultimately, as the organization scaled,

12:57

that DNA replicated. And even if

12:59

the organization grew to be a

13:02

thousand, ten thousand, however big you wanted

13:04

to be, in every meeting, even if

13:06

the original team was not present, you

13:08

could sort of assume that

13:10

the way the people in that meeting

13:13

would approach the problem would carry with

13:15

it these sort of core principles. In

13:18

2015, Ian left Avoz and joined

13:20

another not-for-profit, where the approach to

13:22

culture was, let's say, less rigorous.

13:26

Culture became kind of those principles on the wall or

13:28

like on the website. But if you tapped anyone on

13:30

the shoulder in the middle of a workday and said,

13:32

name the values of the organization, they couldn't recite them.

13:34

And certainly if you said, when was the last time

13:36

that you invoked them with a colleague in the course

13:38

of your work? Never, right?

13:41

And so it was like a human A-B test for

13:43

me. I was in two different organizations, seeing

13:46

what it was like to do intentional culture and seeing what it was like

13:48

to put cultural principles on the wall. And nothing

13:50

could have been more powerful at proving the importance of

13:52

doing that. The

13:54

opportunity to closely compare two vastly different

13:57

approaches to culture is a gift to

13:59

any leader. It hammers home

14:01

what's needed. You can't

14:03

just speak an effective company culture

14:05

into existence. You need to set

14:07

the example of living the culture. That

14:10

is how you truly empower your team to

14:12

embody the culture themselves. Fostering

14:15

a culture of empowerment, communication, and

14:17

similar values is crucially important. It

14:20

cultivates a sense of leadership within every

14:22

team member. It establishes a

14:24

common language and mindset that facilitate

14:27

effective execution of tasks, and it

14:29

shapes the way work is accomplished.

14:32

It's a lesson Ian would draw upon when he founded

14:34

Protect Democracy in 2017, but I'm jumping

14:37

ahead. For now, let's stay in 2015.

14:41

Ian had taken a role at a second

14:43

not-for-profit, coming in as chief operating officer. However,

14:46

his role was soon thrown into turmoil,

14:49

along with his self-confidence. I

14:52

came into that organization as the COO, and

14:54

within three months I was at dinner with

14:56

the founders. They said, this isn't working. That's

14:58

the trust of the organization. We're going to have to demote you. And

15:01

I had to appear in front of the

15:03

entire organization to announce my demotion. I

15:05

asked if I could announce it, and they said, no, we're going to do it. So

15:08

you can imagine how humbling an experience that was. Okay,

15:11

let's just pause here to appreciate how

15:13

this must have felt for Ian. He'd

15:16

been successful in the White House as

15:19

one of the president's most trusted advisors,

15:21

and now he was being very publicly

15:23

demoted. It is hard

15:25

to stumble professionally, but it is brutal

15:27

to have your failures publicly paraded. It's

15:31

also not the end of the world. You

15:33

can springboard from experiences like this to build

15:35

your tolerance for failure and your comfort with

15:37

risk. And that's one heck

15:39

of a perspective to have when you're leading

15:41

through uncharted terrain. Let's

15:44

jump to November 9th, 2016, when

15:46

the seed of what would become Protect

15:48

Democracy was planted. I

15:51

was in voter protection headquarters in Philadelphia in

15:53

this law office. That was one

15:56

of the earliest to see what was happening. There

15:58

was an empty box on the floor. And

16:00

out of frustration, I wound up to kick

16:02

the empty cardboard box into the wall, and

16:05

it wasn't empty. And so

16:07

the box didn't budge. And

16:09

I broke my foot. So I wake up

16:11

the next morning with my broken foot, and there's

16:13

an email from a friend and former partner in

16:15

other projects who had also been in the White

16:17

House Counsel's office a lot after me by the

16:20

name of Justin Florence. And

16:22

the email said, should we get the White House Counsel

16:24

Alumni together and talk about what's coming and whether there's

16:27

something we can do about it. Justin's

16:29

email brought to Ian's mind that bags

16:31

full of binders he'd been tasked to

16:33

collect on that Washington, D.C. evening back

16:35

in 2009. The

16:38

insight was that all those binders that I

16:40

talked about, all those unwritten laws, all the

16:42

ways in which presidents of both parties had

16:45

understood that they were restraints on

16:48

their office and on themselves and that

16:50

they held a public trust, that we

16:53

recognize that with the election in

16:55

2016, something fundamentally different was about

16:57

to happen. And so

16:59

the question was, what would happen if someone threw out those

17:01

binders and said, these rules are for centers.

17:04

Ian and Justin immediately began brainstorming

17:07

ways they could deploy their expertise

17:09

to counter this imminent threat. We

17:12

had a very clear mission statement from the

17:15

get-go, which was prevent American democracy from declining

17:17

into a more authoritarian form of government. As

17:20

an entrepreneur, that mission resonates because

17:22

it identifies an urgent need in

17:24

the market, specifically the

17:26

need to protect American democracy.

17:29

The next thing the founders had to do was

17:31

make the case for why they were the ones

17:34

best placed to help in this monumental task. We

17:37

felt like we had some comparative advantages

17:39

because having been the lawyers inside the

17:41

White House, one thing we really understood

17:44

was how actors outside of

17:46

government could influence

17:48

and impact actors inside of government because we've

17:50

been on the receiving end of that. This

17:53

was their unique selling point. Ian

17:56

and Justin had seen firsthand the potential

17:58

for democracy to be undermined by bad

18:00

actors. Just as white hat

18:02

hackers use their understanding of a

18:04

computer network's vulnerabilities to shored up

18:06

against the malicious attacks, Ian

18:09

and Justin would use their inside

18:11

knowledge to protect the nation's democratic

18:13

processes and institutions. The

18:15

precise tools they would use to do this,

18:17

however, remained unclear. We knew

18:19

the Achilles heels in government, but the actual

18:21

products we were going to need to create

18:23

was a little bit TBD. And

18:26

so we had to build a pretty

18:28

nimble company from the beginning. This

18:31

is such a smart way to approach launching

18:33

an organization. You see an urgent need and

18:35

you know you have the expertise and drive

18:37

to address it, but you lack a specific

18:40

product. If Ian and Justin

18:42

had waited around until they had concrete

18:44

approaches, it might have been too late

18:46

for American democracy. So Ian's

18:48

insight to focus on how to be

18:50

nimble and how to pivot was an

18:52

inspired approach, especially when you consider

18:54

the breakneck speed of politics and the news

18:57

cycles at the time right after that election.

18:59

Time was of the essence. Ian and

19:02

Justin had their mission, they had their theory

19:04

of action, they had their nimble approach. So

19:06

what did they do next? Nothing.

19:10

About two or three weeks

19:12

go by after the election and are

19:14

we really gonna start a new organization?

19:16

We just didn't have quite the confidence

19:18

we needed to do that because

19:20

it takes a lot of huts but to start

19:22

a new organization. Hey look,

19:24

we've all been there. These feelings

19:26

are usually in direct proportion to

19:28

the size of the task. And

19:30

what could be bigger than saving

19:32

American democracy? As is

19:35

so often the case in these crisis

19:37

of confidence moments, the reasons not to

19:39

act started piling up. You

19:41

know at the time not only did I have

19:44

a broken foot but I had my first child

19:46

do in two months. I had a good job

19:48

at another really wonderful nonprofit at the time called

19:50

GiveDirectly. So this notion of like are you

19:52

gonna start something new? We just didn't have that bump to

19:54

get over that hump that I'm sure a lot of founders

19:56

know that moment. We've heard it so

19:59

many times on this show before, but it's

20:01

still hard to imagine for leaders as

20:03

capable as Ian. Fortunately, he

20:05

soon received a call that helped him

20:07

rebuild his confidence. It was

20:09

from two of his former colleagues in the White

20:12

House Counsel's Office, Karen Dunn and Blake Roberts. They

20:15

said that there had been a meeting in Washington, D.C. that

20:17

day of a lot of meeting lawyers in

20:19

the district, people who had led the Department of Justice

20:21

also had been in the White House Counsel's Office, and

20:23

that there was a discussion that there was a need

20:26

for a new organization given the moment

20:28

we were in, and my name was floated as

20:30

someone who should lead it, and everybody agreed. That's

20:33

quite a moment. Yeah, it

20:35

was a moment I'll never forget, both

20:37

for its what. People really think I

20:39

can do this, right? That sense of

20:41

it was humbling, it was flattering,

20:44

but most importantly to the story, it was

20:47

confidence building. And

20:50

maybe not just confidence building, but there was also a little

20:52

bit of, uh-oh, people expect me to do something, right?

20:55

Well, and also you just recently suffered this

20:57

gut punch of being demoted

21:00

publicly in the company and the not-for-profit

21:02

you were working at. So I

21:04

hear you on the, it takes chutzpah to write

21:07

out these culture principles and this mission, and then

21:09

to get this phone call. Where did you summon

21:11

the confidence having just recently been knocked down a

21:13

peg? How did you manage through that? I

21:16

remember vividly getting the call from them

21:18

and flashing back to when I started

21:20

in the White House Counsel's Office as

21:22

a baby lawyer in 2009. And

21:24

I went into the White House Counsel's Office

21:26

and I thought, I don't know a lot

21:29

about how this place works. I

21:31

should really sit back and listen. And so I

21:33

would go into every meeting in the West Wing

21:35

or the Executive Office building, and the first thing

21:37

I would do is I would take the feet

21:39

furthest from the center of the room. I would

21:41

go sit against the walls of Wal-Thark, and two

21:43

of my colleagues, who were pretty much the same

21:45

vintage attorneys that I were, they'd go

21:47

sit at the head of the table. And you know

21:49

what? People treated them like they ran the meeting. And

21:52

it was a real lesson in people

21:54

will treat you the way you act. And

21:56

that doesn't mean that you have to be overconfident. It doesn't mean that there

21:59

is an important place to be. for humility and curiosity

22:01

and lifting and asking questions, but if

22:03

you treat yourself as on the outskirts,

22:05

then you'll be treated as on the

22:07

outskirts. With this

22:09

lesson in mind, Ian seized the

22:11

moment. And I remember saying

22:13

to myself, when you get on that call, you take charge.

22:16

You sit at the head of the room and you tell

22:18

everyone what we're going to do. You listen, but you definitely

22:20

lead. You listen, but

22:22

you definitely lead. I love this

22:24

phrase. It's a concise and

22:27

strong summation of the constant balance all

22:29

leaders need to maintain, and it's applicable

22:31

far wider than the C-suite. It's

22:34

something that every team member should adhere to. If

22:37

everyone acts like they're invested in

22:39

a mission and listens like a

22:41

learner, you'll build resilience, belonging, and

22:43

a propulsive sense of mission throughout

22:45

your organization. With

22:47

this vote of confidence, Ian was reinvigorated

22:50

to launch this new organization, which they

22:52

named Protect Democracy. We'll

23:07

After a word from our premier brand

23:09

partner, Capital One Business. At

23:13

my town hall with my team, I was able to

23:15

sort of declare this new vision for us us to

23:18

become this modern marketing engine. I

23:20

had a lot of skeptics who were like, we've

23:22

seen this, done this, it's not going to work.

23:26

We're back with the Parnasaran of Capital

23:28

One Business. She's recalling a town hall

23:30

where she put forth her data-driven vision

23:32

for overhauling her team's marketing strategy.

23:36

Moving from output-focused

23:38

marketing to outcome-focused marketing.

23:41

When you are outcome-focused, you're actually using

23:43

the data to evaluate whether your strategies

23:46

are effective or not, versus

23:48

output-focused, how many campaigns did I run and how

23:50

many emails did I send, and so on and

23:52

so forth. But not everyone

23:55

was on board. A partner

23:57

realized that her presentation was premature.

24:00

We are not ready to actually declare the vision

24:03

because people didn't buy into your strategy.

24:05

First of all, you just have to get comfortable with

24:07

the fact that people have a right to their own

24:09

point of view. Second

24:12

is understanding that there is

24:14

a story behind the skepticism. And until and

24:16

unless I understand that story, I will not

24:18

be able to turn things around. So

24:22

Aparna turned to her team for answers, something

24:24

she neglected to factor into her initial

24:26

plan. She listened and learned.

24:30

Pay extra attention to what

24:32

they are saying and

24:35

ask a lot of questions. I hear where

24:37

you're coming from, any ideas on how we

24:39

could do this differently. They will

24:41

rightly slow you down and you'll

24:43

be grateful that they slowed you down. And

24:46

it's a good thing they did because a very

24:48

important piece was missing from Aparna's new marketing strategy.

24:51

We'll find out what that was later in the

24:53

show. It's all part of

24:55

Capital One Businesses spotlight on business

24:57

leaders following reads, refocus, playbook. Welcome

25:07

back to Masters of Scale. I'm Jeff

25:09

Berman with our guest, Protect Democracy founder,

25:12

Ian Bassen. If you want to

25:14

hear our entire conversation, you can find that

25:16

on our Masters of Scale YouTube channel. Before

25:19

the break, we heard about Ian's rocky journey

25:21

in the run up to founding Protect Democracy.

25:24

I asked him about those early

25:26

days, taking the idea from concept

25:28

to actual scalable organization. You

25:31

have this concept that you build out, you

25:33

get this call from Karen Dunn, who identified

25:35

the problem, but now you actually have

25:37

to do the thing, right? Just

25:39

like an entrepreneur in the private sector, you've got

25:41

to raise some capital, you've got to figure out

25:43

how you organize. So how

25:45

did you actually get this organization

25:48

off the ground? I think

25:50

the first thing that a lot of people listening

25:52

to this who either have built or are trying

25:54

to build organizations either have learned or should learn

25:56

now is that nobody quite knows exactly how to

25:58

do it. And so the first thing

26:01

we had to overcome was this notion of, well, we don't

26:03

know how to do this. Who knows how to do this?

26:05

There must be an expert way to do this. And the

26:07

answer was nobody really knows. And so we had to come

26:09

up with, for example, a budget. Well, how do you build

26:11

a nonprofit budget? I Googled it. I Googled,

26:13

how do you build a nonprofit budget? And

26:15

then we started mapping out with a nonprofit.

26:17

And first off, just having the sense that

26:19

there is no secret way. This

26:22

brings to mind a favorite master's of scale

26:24

metaphor, courtesy of Reed Hoffman. Entrepreneurship

26:27

is like jumping off a cliff and building the

26:29

plane on the way down. A

26:31

lot of the time you make that jump without

26:33

even knowing how to build the plane. And you

26:35

also need to hope that you can somehow source

26:37

the essential components, the wings, the engine, the fuselage,

26:39

all while you are in free fall. In

26:42

this case, there were plenty of people who

26:44

believed passionately and protect democracy's mission and were

26:46

prepared to hand airplane parts to Ian and

26:48

Justin. Those people included Reed

26:50

Hoffman, who I introduced to Ian around this

26:52

time. I knew of Reed's

26:55

deep belief in the need to protect

26:57

our democratic institutions. Reed

26:59

also brought a venture capitalist's eye

27:01

to investing and protect democracy. One

27:04

of the things that I think is most fundamental to

27:06

the health of our society, the health of our democracy,

27:09

is to pursue the rule of law. And

27:11

so it was like, okay, classic Silicon

27:13

Valley venture investing was

27:16

to say, okay, if you, Jeff,

27:18

rate Ian, then we should

27:20

put in money, we should get it going. And

27:22

it was the equivalent of a seed

27:24

bet in venture. It was the, okay,

27:27

good talent, good plan, really important outcome,

27:29

go. So there's a

27:32

clear parallel for setting up

27:34

the organization where the organization

27:36

starts with no demonstrated product

27:38

service, you need seed financing to

27:40

do that. That was essentially what

27:42

I was providing. And ultimately, as

27:44

part of providing that, then Ian

27:47

and protect democracy could start showing

27:49

that they were part of trying

27:51

to keep the system at a

27:53

high integrity and coherence in the

27:55

rule of law, such that it

27:58

was bipartisan, or actually, frankly. multi-partisan.

28:01

And so once it got

28:03

there, then they could do fundraising and

28:05

get grants from foundations and other kinds

28:07

of things once they'd proven the venture

28:09

out. And then that allows them to

28:12

get on a path of scale. This

28:14

venture seed funding also helped protect democracy

28:16

secure position that is coveted in the

28:18

world of business. First mover

28:21

advantage. We were first

28:23

to market. People were incredibly

28:25

disoriented, alarmed, concerned about what was

28:27

happening in this country. We got

28:29

to them first and

28:31

we had a proposed set of solutions that we thought we

28:33

had a pretty good theory behind and

28:35

we had a network. Because we had all

28:38

of those things, we were able to assemble

28:40

the money, the talent, the

28:42

partnerships, the media attention. There were

28:44

a lot of organizations that came

28:46

along months after us trying

28:48

to do some similar types of things I think

28:51

at a much tougher time because

28:53

they didn't have that sort of perfect set of inputs that

28:55

we had at that moment. Early

28:57

on, Ian received key advice that

28:59

ensured those early vital stakeholders would

29:01

stay engaged with protect democracy. One

29:05

of the best pieces of advice I got was

29:07

from Bree Pettis, one of the Godfathers of 3D

29:09

printing. He said, look, with your

29:11

group of investors, just send

29:13

them a quick 10-minute note every

29:16

like three weeks with what's

29:19

going well and what you're worried about. Keep

29:21

them invested in what's going on

29:23

and solicit them for advice on

29:25

what your problems are. You

29:27

will create not just investors but partners in

29:30

doing that. I've done that for eight years.

29:32

Every couple weeks we send a really candid note

29:34

to all of our key partners. Here's what we're working

29:36

on, here's what's going well, here's what we're worried about

29:38

or what we need help with. And what we've built

29:41

is a community of investors and partners

29:43

who are not just people who kind

29:46

of check and then go away but are intimately

29:48

involved in the success or failure of the organization

29:50

day to day. It's an

29:52

incredible note. I think it'd be helpful for a

29:54

lot of people to think about how to engage

29:57

investors and frankly other stakeholders because I think we

29:59

often under a how much people want

30:01

to help when they're aligned with

30:03

the mission, whether you're a for-profit or

30:05

not-for-profit or other. Ian

30:07

layered an extra challenge on top of

30:09

the founding of Protect Democracy, the

30:11

decision to be a remote organization from

30:14

the outset. Now, this was back in

30:16

2017, three

30:18

years before COVID would force companies

30:20

to hastily pivot to remote working.

30:23

I asked Ian why they made that choice.

30:26

I had been at some remote organizations before, and

30:28

some of the things I observed about them was,

30:31

I think distributed organizations are able to be much more intentional

30:33

about setting the kind of culture that they want, and

30:36

people are able to be a lot more efficient, because

30:38

people don't have the problem that you have in

30:40

an in-person organization where you're in your zone, you're

30:42

in your flow, and then someone walks up

30:44

to your door and they come into your office, and it's good for

30:46

them to talk right now, but it's not so good for you to

30:49

talk right now because you were in your flow, but

30:51

now you're like, well, this is my colleague. So

30:53

there's a lot of inefficiencies about the physical office

30:55

space that you eliminate a lot when people are

30:57

distributed. And so we have staff in probably

30:59

about 26 states, and for

31:01

us as an American democracy organization,

31:04

that's also crucial, because if we're

31:06

going to play any role at

31:09

trying to protect and ultimately strengthen and advance American democracy,

31:11

we need the wisdom of people from all over this

31:13

country. And if we were to

31:15

confine ourselves to just the Tylenar Washington, or

31:18

just the Tylenar New York, we'd be limiting

31:20

the talent pool enormously, and who we'd be

31:22

competing with would be challenging as well, whereas

31:24

once we brought into the entire country, we

31:26

get access to all sorts of talent everywhere.

31:29

I hear all those benefits, and I love

31:31

that you've leaned into what others might perceive

31:33

as a challenge and turned it into a

31:35

strength. There are two elements

31:37

of this that I'm struggling with

31:40

for the first time leading a distributed organization, and

31:42

I'm curious how you deal with them. Number one,

31:45

so much of my learning in my career is

31:47

similar to that seat that you took on the

31:49

back bench in the White House, where

31:51

you're listening and you're learning and you're seeing how it's

31:53

done. That's really hard to do

31:55

in a phone and video conference environment.

31:58

Two is the interstitial. time. You're

32:01

walking through the office and yes, someone's in flow.

32:03

You don't want to rip their flow, but you

32:05

can see that something's off with them. And you'd

32:07

say, Hey, let's go take a walk. Let's grab

32:09

a coffee or whatever, and just check in and

32:11

how are you doing? Everything okay. So

32:13

have you figured out how to solve for that? And if so, how

32:15

have you done it? Well, this goes

32:17

again to the point that you can do all

32:20

of those things and they're much more intentionally injected

32:22

into what we do. So for example, on the

32:24

sort of learnings piece, right? What you observe and

32:26

learn. We have a practice where midway through and

32:28

at the end of every project, we do an

32:30

after action session where we look at what's working,

32:32

what's not working, what lessons can we draw from

32:35

here for other things? And then we read those

32:37

out to the entire team. So everyone benefits from

32:39

those lessons. I'm going to break

32:41

in here and punctuate Ian's in-depth answer to

32:43

my question. It contains so

32:45

much actionable material for building an

32:47

invested culture, whether you're fully remote,

32:50

fully in person, or somewhere in

32:52

between. In this instance,

32:54

Ian is intentional in building out moments

32:56

of reflection. This is a

32:58

deep impact on the tactical, strategic

33:00

and cultural levels that protect democracy.

33:03

People gain clarity on what they need to do

33:05

immediately and why they get a

33:07

bigger picture view of how that action

33:09

will meaningfully move the needle in terms

33:12

of mission. And these moments reinforce a

33:14

culture of inclusion in which everyone has

33:16

ownership of decisions. Okay. On

33:18

to Ian's next insight about the benefit

33:20

of being remote from the very beginning.

33:23

In terms of the interstitial picking up on how

33:26

people engage with each other, we've adopted a practice

33:28

I think originally came from Priya Parker, whose work

33:30

you may know talking about the art of belonging

33:32

and how people get together, which will restart every

33:35

meeting with people sharing their state of mind.

33:37

Zero, one, two, three in the positive side, or zero,

33:40

negative one, negative two, negative three on the negative side.

33:42

We go around, everyone quickly says, where are they on

33:44

that scale and what might be informing it? And that

33:46

immediately gives people the signal that, you know what, Jeff's

33:48

a negative two today. At the end of

33:50

this meeting, I might grab them and pull them aside and see what

33:52

I can do to help them. This

33:55

is a terrific example of how to

33:57

bridge the emotional disconnect that can come

33:59

from working remotely. in a fast-paced organization.

34:02

Let's turn to one particularly surprising pillar

34:04

of Ian's approach to making remote organization

34:06

work. It's one that I don't think

34:08

is widely considered. This is

34:10

really important. No headquarters. If

34:13

you want to be a distributed organization successfully, you can't

34:15

have one place that the headquarters and everyone else is

34:18

sort of somewhere else. There can be no headquarters, because

34:20

otherwise, the people who are not in it, they feel

34:22

second class. They feel like they're missing something, and there's

34:24

a locus of energy. It's got to be fully distributed.

34:27

This is more than just a naming convention.

34:30

How Ian has achieved it speaks to

34:32

how intentional he's been from day one

34:34

regarding culture and his commitment to distributed

34:36

working. Post-pandemic, there are

34:38

so many organizations grappling with the

34:41

challenge of remote and hybrid work.

34:44

I think this question of having a headquarters,

34:46

whether a name or in spirit, is overlooked.

34:49

Working remote should not mean feeling

34:51

remote. You've got to bring

34:53

people together for multi-day off-sites multiple times a

34:55

year. And what's important about those

34:57

off-sites is they're not about, let's

34:59

come up with a strategic plan. What

35:02

are OKRs going to be for next year? That's not what

35:04

you use them for. You can do that when everyone's back

35:06

in their hometown. Those are for really

35:09

building those deep connections with each other. Building

35:11

connections is also at the core of Protect

35:14

Democracy's work. As we've heard

35:16

throughout this episode, the only way Protect

35:18

Democracy can succeed is through building a

35:20

broad coalition, one that cuts through political

35:22

divides. It is, I think,

35:24

a singular problem that Ian faces. And I

35:27

asked him how he tackles it. You've

35:29

assembled a team of people

35:31

who have worked for everyone

35:34

from Elizabeth Warren to Ted

35:36

Cruz and Jim DeMint and

35:38

John McCain. How

35:40

have you created a culture where

35:43

people with such radically different political

35:45

belief systems, political philosophies on so

35:47

many issues can come together

35:50

and focus in on the single mission so

35:52

well? First off, we

35:54

have to do this as a country. If

35:56

we can't, in an organization committed to Protecting Democracy, bring a

35:59

nation, we can do it. people together across political

36:01

differences, how do we expect the country to be able

36:03

to do it? There are those

36:05

things that are necessary and fundamental for

36:07

a country to be democratic. Can

36:10

you peacefully protest your

36:12

government without being violently attacked by

36:14

the government's military without any accountability?

36:17

Can you, if you're an eligible voter, easily access

36:19

the ballot, have your vote counted when

36:22

someone actually gets the most votes in the rules that exist

36:24

at the time? Are they the person who gets inaugurated or

36:26

is there an effort to thwart their inauguration? Those

36:29

are things that are foundational to a democracy and those are the

36:31

things that we work on. That

36:33

actually brings together a lot of Americans across

36:36

a lot of political differences who fundamentally agree

36:38

with that. The majority of Americans agree with

36:40

that. And so we're able to

36:42

bring people together who disagree, but we agree

36:44

on the fundamental values of democracy. We're

36:47

a company like any for-profit company that

36:49

has a specific thing that we do,

36:51

a widget that we sell, a mission

36:53

that we try to serve. It is

36:55

for us to prevent American democracy from

36:57

declining into a more authoritarian government, just

36:59

as for Pepsi, is to sell soda,

37:01

right? How do you

37:03

think about both competing with and cooperating

37:05

with other entities that are

37:07

focused on the same mission that

37:09

protect democracies? Well, we

37:11

have a word for it. We call

37:13

it co-opertition, which is one of the

37:16

unique dynamics of the nonprofit sector. In

37:18

the for-profit sector, it is assumed that

37:20

companies will compete against each other. It

37:22

is considered a good, a necessity, because

37:24

as they compete, they force each other

37:27

to out-innovate one another, and the entire

37:29

sector moves forward. And

37:32

the assumption in the nonprofit sector

37:34

is that we should all

37:36

just be cooperating with each other, and that

37:38

you'll hear this a lot from investors, from

37:40

donors, saying, well, are you guys duplicative of

37:42

each other? My

37:44

response is, well, you do want us

37:47

to cooperate with each other. If we

37:49

develop an innovative strategy

37:52

to advance the

37:54

ball of our democracy, we should share

37:56

it with the entire sector. We

37:59

do that in the nonprofit sector. really important because we do

38:01

have a shared mission. At the

38:03

same time, the notion that we should collapse

38:06

all of the entities in the nonprofit space and

38:08

just have one and no duplication, you'd

38:10

eliminate competition, you'd eliminate innovation, you'd

38:12

actually create a less

38:14

good customer experience and less advances.

38:17

You want a little bit of competition because

38:19

I will tell you the truth is because

38:21

we as an organization have to compete for

38:23

donors, we have to compete for talent, we

38:25

have to compete for media attention, we have

38:27

to compete for meetings with legislators, that drives

38:30

us to do better. And

38:32

so the nonprofit space has to compete and it

38:34

has to cooperate, it has to have

38:36

co-opetition. One of

38:38

the other interesting points of

38:40

commonality between for-profits and not-for-profits

38:43

is success on

38:45

mission tends to buoy

38:47

or depress spirits, right? I'd

38:50

love to hear one, where

38:52

you are on mission and

38:54

two, how you keep the

38:57

team's spirits buoyed when they're

38:59

concerned that they're not achieving

39:01

mission. It all rests upon

39:03

that cultural foundation we talked about earlier, but there are moments

39:06

that I have my doubts, as everyone on the team does.

39:08

And I remember one of them came in the fall of

39:10

2020 as we were approaching the election

39:13

and as an optimist, I generally think that it is more

39:15

likely than not that we will end up in a better

39:17

place in the future. And I had dipped

39:19

into a place where I thought it was actually only

39:21

a 49% chance that we would

39:24

end up in a better place and that more likely

39:26

than not we would end up in a very dark

39:28

place. And I remember I reached out to

39:30

a mentor of mine and I said, how do

39:33

I lead a team if

39:35

I actually have dipped into that place and caused a

39:37

missile? And he said to me, you

39:40

may think there's only a 49% chance of

39:42

success, but do you believe

39:44

that you and your team and the American

39:46

people have the agency to add that 10%

39:48

to tip us back to 51? Is

39:51

that within your control to do? And

39:53

I remember thinking, absolutely. We absolutely

39:55

have that agency. So then lead from there.

39:58

And I bring that up. to the team

40:00

and I encourage the team to think that way

40:02

as well, which is that authoritarianism thrives

40:06

on holiness, on despair,

40:09

on a feeling of isolation and that nothing

40:11

can possibly get better. And democracy

40:13

as a form of government isn't

40:16

just a set of laws

40:18

or amendments and a

40:20

constitution. Alexis de

40:22

Tocqueville referred to the habits of the heart in

40:24

America that make us a democratic society. It is

40:26

what we carry with us every day and what

40:28

we do. It is that belief that we

40:30

have the agency to chart

40:33

our own future. And so even in

40:35

a moment when members on our team

40:37

or listeners to this podcast think

40:39

we're trending towards a dark place, the

40:42

truth is that we have the agency to change

40:44

that outcome. And I look

40:46

forward to being able to do that so that hopefully

40:48

we can do one thing that a

40:50

nonprofit should do that perhaps a for-profit should never

40:52

do, which is put yourself out

40:54

of business. If

40:56

we're ultimately successful, then we

40:59

will no longer need to exist. I

41:01

love that and I love what I'm

41:04

going to start referring to as the 2%

41:06

principle, because this

41:08

idea that boy if you're just on the

41:10

wrong side of that optimism-pessimism line, if

41:13

you and your team really believe that you can

41:15

tip that scale just that small amount, you don't

41:17

have to get it to 100%, you

41:19

just have to get it to 51% to

41:21

really believe and get back on the horse and ride into

41:24

battle. I think that's an extraordinary

41:26

lesson and principle for us to take

41:28

into our workplaces, not for profit, for

41:30

profit or other. So thank you,

41:32

Ian. I'm grateful for that insight for

41:34

those lessons and for your time today.

41:37

Probably got to talk to you, Jeff. I'm

41:40

Jeff Berman. Thank you for listening to Masters

41:42

of Scale. And

41:46

now a final word from our brand

41:49

partner, Capital One Business. What

41:54

was very clear was that the customer was missing. We're

41:57

back one more time with a partner. Erin

42:00

of Capital One Business. She

42:02

had learned that she couldn't refocus her

42:04

department strategy without bringing her team along.

42:07

And that meant listening when they told her what was

42:09

missing, the customer. Aparna

42:11

realized that putting the customer front and

42:13

center would actually unify her team. I

42:17

have folks who are traditional marketers and

42:19

customer is the top thing on their

42:21

mind. And then I have analysts who

42:23

spend their time on data. And it's

42:25

very easy to get stuck into that

42:28

domain. I have

42:30

a real opportunity to get both

42:32

sides to see each other's perspective and meet

42:34

in the middle. Because

42:36

Aparna's team couldn't pivot without bringing

42:38

the customers along. We

42:41

call ourselves team magnet. Our

42:43

job is to attract and retain

42:45

customers. So it just creates a

42:47

sense of working together. Aparna's revised

42:49

vision statement calls team magnet

42:51

a customer centric data powered

42:54

machine. The vision statement

42:56

that I have right now is

42:58

a hundred times better version of what I

43:00

had at the beginning of the year. And

43:03

it has evolved and improved as a result of

43:05

these conversations we've continued to have within

43:07

the walls of our team. Capital

43:10

One Business is proud to support entrepreneurs

43:12

and leaders working to scale their impact

43:14

from Fortune 500s to

43:16

first time business owners. For more

43:19

resources to help drive

43:21

your business forward, visit

43:23

capitalone.com/business hub. That's capitalone.com/business

43:25

hub. Through

43:50

notes, mixing and mastering by

43:53

Aaron Vasanelli, original music

43:55

by Eduardo Rivera and Ryan Holliday.

44:00

all!!