March 5, 2025 • 29 mins
Andy Tobias is one of the most well-known financial thinkers in America and was the treasurer of the Democratic National Committee for almost 20 years. He's also the author of "The Best Little Boy in the World." Often considered the first book to openly address gay American life, it has impacted over a million readers. Andy reflects on his own life experiences trying to be "the best little boy in the world."
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Speaker 1 (00:00):
But We Loved is a production of iHeart Podcasts and
The Outspoken Podcast Network. Hey, this is Jordan. This is
our last episode of but We Loved, and I want
to thank you so much for being on this journey
with me. This was my first professional endeavor as a
journalist and to think we've made forty episodes, forty emotional, surprising,
(00:26):
revealing episodes. I'm just so grateful for your support. I
don't know if but We Loved we'll be back, but
I want you to stay with me on my journey.
If you haven't already, go follow me on Instagram or
TikTok at your underscore again, Solvice. That's Jar Underscore g
O n SA l VS. I'm going to be producing
(00:49):
a TV series called Unshaming as my next career move,
where I interview people on the shame that they've overcome,
and I want you to stay in touch with me.
I read every letter you send, every message that I
get on Instagram from you, and it means a lot.
I want to say thank you for all of the
encouragement and I cannot wait to take you with me
(01:11):
on this next huge part of my journey. Thank you
so much. Now let's get into the show.
Speaker 2 (01:17):
So I had an agent. I made an appointment to
see him, and I brought the manuscript and I said, Stirling,
I made sure the door was closed. Nobody else, none
of the secretaries could here. I've written a book. It
has to be under a pen name. Nobody can know
I wrote this book. I don't know if there's a
way you can do that. I'd like to get it published.
(01:38):
I'd like you to read it. Are you willing to
read it? On that basis? And no one will ever
know that it's me? And he said okay. And the
next day he called. He said, I want to got
to published, and basically he did. This was kind of
the first one written about coming out. Everybody in the
(01:59):
whole world knew basically accept my parents.
Speaker 1 (02:10):
As a gay kid, growing up religious and in the South,
I thought being gay was the worst thing I could
ever be. Now, as a journalist, I'm trying to unlearn
that by seeking out our history, and what I've found
are people and stories full of courage, perseverance, and love.
In this episode, we'll meet Andy Tobias, the author of
(02:32):
the legendary book The Best Little Boy in the World.
We'll learn about the loneliness that he battled before coming out,
and for Andy, what he believes is the opposite of
that loneliness. For my Heart podcasts, I'm Jordan and Solves,
and this is what we loved. In my first year
(03:14):
of coming out, I read almost all the popular gay
self help books, and one of them was called The
Best Little Boy in the World. Before I even knew
what the story was about. It almost felt as if
the title of the book looked me up and down
and tore into my life story. It's about a syndrome
that so many queer people share, the idea that we
(03:38):
can deflect from our shame of being gay by overachieving.
I can overcompensate with accomplishments at school and at work
and in the gym for the fact that I don't
believe I'm truly lovable. I can compete against others and
be the best, which will give me an artificial sense
(03:58):
of self worth that I don't have on my own.
It was familiar to me because it was my story
growing up. I learned very early on that the accomplishments
my parents could brag about were like a currency for approval.
When I was thirteen, I got into one of the
most competitive high schools in my city. In college, I
(04:22):
landed one of the most competitive internships at Google, and
I won the opportunity my senior year to give the
student commencement speech at graduation. I had hoped to that
by being the best little boy in the world, the
best high schooler, the best intern, the best everything, it
would distract from my deep inner belief that I wasn't
(04:44):
worthy of love. But it didn't. It just left me
on top of a big pyramid of achievement by myself alone.
When I read the book, it gave me language for
the first time to explain this experience, and it helped
(05:05):
me realize that my accomplishments would never soothe my innate
need to be loved. My next guest, Andy Tobias, is
the author of that book, The Best Little Boy in
the World. According to Amazon, it has sold over a
million copies since it first came out in nineteen seventy
three and has never gone out of print. The book
(05:28):
has touched the lives of countless queer people across decades,
including many of my guests this season. Andy would go
on to become one of the most well known financial
thinkers in America, writing for Time, in Esquire and New
York Magazine. He's written multiple best selling books on money
and investing, and for many years was the treasurer of
(05:49):
the Democratic National Committee. But long before that, in the
fifties and sixties, when he was growing up, Andy Tobias
was also the best little boy way in the world.
What was that moment for you when you knew that
(06:12):
you were gay or different for the first time? As
a child, we.
Speaker 2 (06:16):
Went to Palm Springs. My stayed at my grandmother's place.
Who knew that Palm Springs would become a gay mecca.
And I couldn't have been eight, so I must have
been ten, and I was thumbing through a Sports Illustrated
and I saw a particular picture that, oh, wow, boxer
with us. You know, I probably somebody who had just
(06:37):
won the lightweight something or other than Sports Illustrated. But
there were stirrings' There hadn't been stirrings before that, I remember.
Speaker 1 (06:51):
So what kind of messages were you getting about being
gay in the fifties?
Speaker 2 (06:57):
So basically I was watching tea in the den up
in the country on a little black and white TV.
Because this is nineteen fifty seven and I'm ten. This
is now sixty seven years ago or almost sixty eight,
and I remember it like it was yesterday. Ben Kosovar,
who was an army buddy of my dad, comes through
with my dad and they were talking about something and
(07:18):
all they were just walking through the hallway, and the
one snippet I heard was Ben Kosovar saying, oh, he's
a homosexual. And they were gone, and I'm thinking, oh
my god, that's the word for it.
Speaker 1 (07:36):
You didn't even know what they were exactly. You didn't
hear talking about.
Speaker 2 (07:39):
Some awful person who was a queer, and which is
the worst thing you could possibly be in nineteen fifty
seven among the straight guys. My father was a wonderful,
wonderful man, my mother was a wonderful woman. But they
hated gay people because everybody did or or they you know,
they pitied them, and they it was just a horrible
horror thing to be. You didn't want to have anything
(08:02):
to do with gay people. So I knew, and from
age ten to age twenty two, I had this terrible
secret that no one could ever know. And there was
no question about it. The only issue is how am
I going to hide it for the rest of my
life and how am I going to have a life
because I probably won't be able to. I thought about
(08:24):
it constantly, especially once the hormones kicked in more or
less that year, and the next year and the year after.
So for the next twelve years, which is a long
time when you're ten, to keep this secret, and Jordan,
I thought about it constantly. I was afraid of everything,
including talking in my sleep. That was the one thing
I couldn't totally necessarily control.
Speaker 1 (08:46):
You talked about kind of this experience with your dad
and his friend in the army and understanding that that
was a bad thing to be gay. What did that
mentality sort of create for you in the next chapter
of your life.
Speaker 2 (09:04):
I spent the next twelve or thirteen years being deeply,
deeply in the closet and trying to do everything right,
trying to get the best grades I could, trying to
get my little varsity letters. I had to go to
Harvard because my brother, my older brother, Goliath, who was
four years older, almost four years, he had gone to Harvard.
I was very competitive with him in a way, I guess,
(09:25):
and so would look for any opportunity to be the
better performing child. So he would get in trouble, and
I would oh, Andy's such a good boy. And when
it was time to apply to schools, I didn't know
where to apply, and I really was very out of
it in so many ways, including this one. But my
(09:47):
parents said, well, you're applying to Harvard. What do you mean?
And I said, well, yeah, but okay, where else? They said,
what do you mean? Where else? You're applying to Harvard?
And I said, what if you don't get in? I
had to go to Harvard, and thank Heavens, I got
in because I would have been deep trouble, I guess
with the Supreme Court if I didn't.
Speaker 1 (10:06):
Well, how was it at Harvard being gay? I mean
I came out my senior year of college, and I
feel like those years were turmoil for me because it
was becoming harder and harder and harder to conceal my
sexuality and stay in the closet even to myself. What
was it like for you during those years in college?
Speaker 2 (10:30):
Well, in high school I was in love with various people,
I mean deeply in love, but couldn't do anything. And
in college I was madly in love with a whole
succession of people, none of whom ever knew. I mean
two of my roommates. One went on to be mayor
of Cincinnati, and the other roommates that I was in
love with became dean of students at the University of
(10:52):
British Columbia with sixty five thousand students, and oh my god,
college was so lonely on Saturday nights day and everybody
else would go out looking for women. Harvard was all
I pretended. I hated it, but there was all guys
and we weren't even allowed to have women in the
rooms except for it was called parietals, and the parietals
(11:12):
on weekdays.
Speaker 1 (11:12):
I think, oh, this was before it was a co ed.
Speaker 2 (11:15):
Ye. Yes, we had electricity, but we didn't have women.
So Saturday nights Arnt and Brian and the others would
go out to parties and looking for chicks and all
these things. And I would pretend that I had a
turn paper I had to do, or this or that
the other thing. I was very busy with extracurricular stuff.
But what I would really do Saturday night, I would
(11:35):
sit alone in our dorm room or our suite I
guess you call it, with the lights off. I would
listen to albums over and over again. One Johnny Mathis.
The album is called Heavenly. It is the most romatic
album you will ever hear. And I would listen to
these love songs basically they were so beautiful and the
express the yearning, the yearning and the yearning and the
(11:59):
yearning that I've felt. That's how lonely I was, and
so that really spoke to me.
Speaker 1 (12:04):
So andy. At some point in your coming out journey,
you decide to write this book, The Best Little Boy
in the World. What was that like?
Speaker 2 (12:14):
When I was twenty three, I went back to business
school basically to have something respectable to do while I
came out of the closet. I was did very little
of the homework, and I was terrible in the classroom
and all that kind of stuff. But I needed some cover.
I needed something respectable to do.
Speaker 1 (12:32):
This was another form of compensation, another form of being
the best twenty three year old boy in the world.
Speaker 2 (12:39):
You know, I was my cover story. Every night, while
I was supposed to be studying the cases, I would
get in my little eighteen hundred and eleven dollars Fiat
Spider and drive down to Sporters, which was the bar
of k bar, of course, and there were like four
bars in Boston, and this was the kind of the
collegiate one and where I might meet somebody that I like.
(13:03):
But that summer I realized, hey, this is crazy. Some
of the people I'm meeting the bar. One of them's
a priest, one of them is a cop. So after
a couple of years, when I was just finishing business school,
I'd already had some stuff in New York magazine for
other reasons, and I realized I should write about this.
(13:24):
This is an unbelievable story. There is this whole world
out there that millions of people know about, including some
straight people, mostly gay people, but straight you know, in
the theater and this and a lot of people know it,
and nobody else knows, but most of America know it,
just wasn't discussed and so on and so forth. So
(13:46):
what a book, What an opportunity to now. I was
not brave in any way, so I couldn't let anybody
know that I wrote the book. But I wrote this
book under a pen name. I remember going kind of
vibrating with nervousness and sweating. I went to my agent,
because I had a literary agent, because I had.
Speaker 1 (14:07):
This is the best little boy in the world. You
write this book.
Speaker 2 (14:10):
Yeah. Before that book, I had had a couple other books,
and I'd had articles. I was on the cover of
New York Magazine and all these kinds of things. So
I had an agent and he was such a straight
lace waspish well I can say his name is passed on,
and he was in many ways a wonderful man. His
name was Sterling Lord. I made an appointment to see
(14:30):
him and I brought the manuscript. This is before PDFs
or any of that stuff. So I had one copy.
I guess I made a xerox or something. I brought
the manuscript and I said, Sterling. I made sure the
door was closed. Nobody else, none of the secretaries could here.
I've written a book. It has to be under a
pen name. Nobody can know I wrote this book. I
(14:51):
don't know if there's a way you can do that.
I'd like to get it published. I'd like you to
read it. Are you willing to read it? On that basis?
And no one will ever know that it's me? And
he said okay. And the next day he called and
he said, I want to got to publish, And basically
he did This was kind of the first one written
(15:11):
about coming out.
Speaker 1 (15:14):
So the book comes out and it changes so many
people's lives. It's the first of its kind. But your
parents still don't know that you're gay.
Speaker 2 (15:24):
Everybody in the whole world knew, basically except my parents.
I mean, how could I tell my parents. They loved
me so much and I love them so much, and
this was a terrible thing to be And I didn't
want to, you know. And I thought it over and
over again a billion different times. When I would go up,
(15:46):
you know, get in my car, drive up to visit
them for Thanksgiving or for this time or for that time,
I would think through my head how the conversation would go,
and I would this time, I'm going to do it.
This went on for years.
Speaker 1 (16:07):
By his mid twenties, Andy had graduated from Harvard and
Harvard Business School, and he was a regular finance contributor
to New York Magazine and had even appeared on the
cover of the magazine in nineteen seventy. When he published
The Best Little Boy in the World in nineteen seventy three,
it quickly began impacting the lives of many gay men
(16:27):
across the nation. The initial printing sold thousands of copies
and quickly sold out, and Andy would receive powerful letters
from readers telling him, I can't believe you've written my story.
At a time when being gay was still very shameful,
this was deeply rewarding to him. But even though he
had a full fledged gay life with friends and fans
(16:51):
and even a few romantic relationships, he was still closeted
to his parents.
Speaker 2 (16:57):
The book had come out, it had been reviewed in
The New or Times Sunday. I had had an excerpt
of it in New York Magazine under a pen name.
But I had a friend from high school called from
California say hey, Andy, congratulations on this. You know. I said,
what do you mean, How did you know? He said, oh,
it's obvious your style. You know, it was obvious it
was you. So he knew, but my parents didn't know.
(17:18):
And this went on for years. Okay, the book came
out when I was twenty five. Everybody knew, People at
New York Magazine knew, and I would drive up to
visit my parents and go through my head. Finally, age thirty,
the paperbacks about to come out, and I just couldn't
stand it anymore. And every Sunday, I would call my
(17:41):
parents to say hi, because that's what you do. And
I called my mother picked up, and I said, Mom, listen,
I'm about to tell you something that I either should
have told you ten years ago or I should never
tell you. And this is certainly not the way to
do it over the phone. But I can't stand it anymore.
There's no good way to do it. And my mother
(18:02):
said instantly, okay, but don't tell your father. He's coming
to he's coming to the phone. And so he came
to the phone. So we talked about something else or whatever,
and then I reconnoitered with my mother and I said,
what do you mean, don't tell my father. This went
on for two years. I finally said, Mom, this is
just ridiculous. This is insane. So she said, all right,
(18:23):
I'm going to California. I'll be gone for a few days.
On Sunday, call your dad. Ask him to stop by
your apartment on the on the way in from the
country back into the city, because that's what we did,
and asked him to come by. So I did. He
came by and I basically told him and he said okay,
(18:44):
and I said, what do you mean Okay. I was
kind of expecting that this was I've been I've been
waiting her twenty years to finally and he said, well,
you know, you're not a bad looking guy. You never
bring girls home, you never have, you don't talk about
girls into I can't say I'm completely surprised. So now
I'm feeling you know, I've gone through all that. So
(19:06):
I said, would it surprise you to know I've written
a book about it that was reviewed in the New
York Times? And he said, what what? I So I
gave him the book, and now I wow. I gave
him the book, and it's hard to do the rest
of this way out getting a little choked up because
he was wonderful, wonderful man. And he called at nine
(19:26):
o'clock the next morning and he was crying. It was clear.
I said, why are you crying? He said, I stayed up.
I stayed up all night and I read it twice,
and I just feel so bad that I didn't do
anything to help you. I had great parents, so that's
how I told him. Only took me, you know, twenty
years from when I knew and five years from when
(19:49):
I wrote the book. And I guess I was thirty
two by the time I told my dad.
Speaker 1 (19:55):
The nineteen eighties were a decade of success for Andy.
He became a household name as a financial guru, but
it was also a time of unbearable loss. Andy was
living through the AIDS crisis. He was watching his best
friends get sick and die, Young brilliant men, friends he
(20:15):
had danced with at Fire Island, laughed with over intimate dinners,
friends who had become family to him disappearing one by one.
And at the time, it seemed like the presidential administrations
of Ronald Reagan and George Bush Senior were largely indifferent.
After all, AIDS was a disease shrouded in shame because
(20:38):
it largely affected queer people, a segment of society many
viewed as worthless. But when a young governor named Bill
Clinton decided to run for president, Andy and many LGBTQ
Americans felt a glimmer of hope. Bill Clinton was the
first president to appoint qualified gay Americans into his administration,
(20:59):
showing the nation that LGBTQ Americans were respectable, dignified people.
He also declared war on AIDS and made major strides
in ending the crisis, and when Clinton got elected, Andy
got the chance to tell him thank you.
Speaker 2 (21:16):
Through a series of lucky, odd coincidences, I got to
know the governor of Arkansas, very young guy, at his
very pretty.
Speaker 1 (21:22):
Wife Bill and Hillary Clinton.
Speaker 2 (21:24):
Yeah, and then he went off and got himself elected.
And on January first, nineteen ninety three, nineteen days before
he was in fact going to be inaugurated, they were
he and his wife were at the thing that where
I met him, a thing called Renaissance Weekend that about
thousand people went to, and they put me on a paddel.
They called it a panel, each one with two minutes,
(21:45):
and your assignment was New Year's Day, nineteen ninety three.
What I would say if I had two minutes to
say anything I wanted to the next president of the
United States. And then there was a big, big footnote,
don't expect him to be there. He won't necessarily be there.
I decided I didn't tell anybody. I was too scared
to tell anybody. I didn't tell any of my friends.
The people who knew me there knew I was gay.
(22:07):
I've been gay forever, but there are a lot of
people I didn't know there. But I was so scared
because eight hundred people whatever it was in the audience,
And so I got up there and I say, and
I'm looking straight at him, and I say, if I
had two minutes to say anything, you might expect me
to talk about smoking, because they knew I was a
(22:28):
big anti tobacco guy. But really, there's only one thing
I could say, which is thank you. You haven't even
taken office yet, and already you have dramatically improved my
life and the lives of millions of other gay and
lesbian people around the world. So I did my little
two minutes on that, and the response I got afterwards.
(22:48):
Remember this is nineteen ninety three, long after Snowmall much
progress had been made. But Bill clint was the very
first presidential candidate who would ever put our topic on
the national stage and who had ever done a fundraiser
with LGBT people when he was a candidate.
Speaker 1 (23:05):
And this is the backdrop of all of this, is aids.
Speaker 2 (23:09):
Yes, I lost half my friends and age they died.
Half my friends, including my partner of seven years, Scott.
Speaker 1 (23:18):
You know when you were talking about coming out to
the Clintons, it made you emotional. I wonder why that
that was such a touching moment in your life.
Speaker 2 (23:30):
A couple of weeks ago, I had the opportunity to
throw a wedding for my two best young friends. I'd
never thrown a wedding before, and I was the epiciant,
and I was going to I decided not to say
this because it was about them, not about me. But
I was thinking, as I kind of m seed the
thing I was thinking of saying. You know, a lot
of you think that I walked down here, like eight
(23:52):
blocks from south from where I live, which is true,
But really the journey started about eight blocks west and
twenty blocks north. And it's been seventy seven years, and
I get emotional because we have been through so much.
Speaker 1 (24:21):
By the late nineties, Andy had become an important voice
in Democratic politics. As the treasurer of the Democratic National Committee.
He would help prop up two wildly successful presidential campaigns
for President Obama, and at one point had become one
of the highest profile gay public officials in America. As
part of his service, in twenty thirteen, he traveled to
(24:43):
China and came out to the country's Vice president. Andy,
once a lonely gay child who hid his sexuality and shame,
had completely transformed into a global advocate for LGBT causes.
Speaker 2 (24:57):
So I got a call from Howard Dean, who had
been the governor of Vermont and had been the chair
of the Democrat National Committee, so I knew him that way.
And he said, Andy, there's this thing. Every six months
they have some Democrats and some Republicans go to China
and then every six months the Chinese Communist Party come
to Washington. I've done it twice, can't do it again.
(25:18):
You should be one of the three Democrats who goes.
It's an exchange between the parties of the United States
and the Party of China. And I said, you crazy.
I don't know anything about I don't speak.
Speaker 1 (25:30):
Chinese, I don't when was this.
Speaker 2 (25:32):
This was twenty thirteen. But after saying no, no, no,
about a million times, they finally persuaded me to do it.
And I was very nervous about it, and I was
going to have to deal with people that I didn't
know and who didn't certainly didn't know about my life.
(25:52):
And I had been asked to give the first little
remarks with the Vice President of China, and my topic
was supposed to be the you know, gridlock between the
two parties in Congress and all this stuff. I addressed
the topic, and then I said, and if I might,
as a point of personal privilege, as we call it
in the US, I explain that, you know, three of
(26:16):
the nine officers of the Democratic National Committee, including me,
were openly gay. I said, you know, they're probably about
one hundred million gay people and LGBT people in China,
and of your eighty five million Chinese Party of the
Communist Party members, do you have any sense of how many?
You know, how many are in your leadership in America?
(26:38):
He's a professor. Do we know anything about that professor? Whoever?
It was no, but we could look into him all
that anyway. Frankly, it was thrilling to me because the
goal was maybe we can show them that, you know,
this is not a big deal, because nothing to make
a hundred million people happier. Things To make somebody happier,
(27:01):
you need to build things, or you need to grow things,
or you need to you know, hurt somebody else, make
them un more or less happy. Here, you can make
one hundred million people happier just by you know, letting
them live their lives without fear of persecution. That kind
of thing.
Speaker 1 (27:19):
We've talked a little bit about this amazing life that
you've lived. Andy. As gay men, it's no secret that
we tend to chase the ideals of what we think
will make us happy, working out for hours on end
in the gym, in our body, image and sex and wealth.
(27:41):
But what has made you happy in your life?
Speaker 2 (27:46):
Chosen family. I have an amazing family of astonishing friends.
I tell my young friends, if you've got your health,
you've got your friends, you've got a good Internet connection,
and you have purpose in your life, you have everything.
I wrote a book called The Only Investment God You'll
Ever Need, you know, two hundred and whatever pages. I
(28:07):
wrote another one called The Only Relationship Guide You'll Ever Need,
which is just one sentence, so I couldn't actually publish
it as a book. But it's be nice to each
other and find humor in the compromises. They're worth it.
Friends are everything, and so that's the opposite of loneliness.
Speaker 1 (28:25):
What you're saying is it's it's community or family.
Speaker 2 (28:29):
You build your own family.
Speaker 1 (28:35):
But We Loved is hosted by me Jordan Gonsolves. If
you want to write in to tell your story, email
us at but We Loved at gmail dot com, or
you can send me a message on Instagram or TikTok
at your underscore goa and solve this. We are a
production of The Outspoken Podcast Network and iHeart Podcasts, but
(28:55):
We Loved was originally developed with Pushkin Industries. Our producers
are Joe pat Emily Meronoff, and Christina Loranger. Our executive
producers are me Maya Howard and Katrina Norville. Original music
by Steve Boone. Special thanks to Jay Bronson and Roquel Willis.
If you loved this episode, leave us a rating and
(29:17):
follow us on Apple Podcasts and Spotify, and thank you
for listening.
But We Loved is a production of iHeart Podcasts and
The Outspoken Podcast Network. Hey, this is Jordan. This is
our last episode of but We Loved, and I want
to thank you so much for being on this journey
with me. This was my first professional endeavor as a
journalist and to think we've made forty episodes, forty emotional, surprising,
(00:26):
revealing episodes. I'm just so grateful for your support. I
don't know if but We Loved we'll be back, but
I want you to stay with me on my journey.
If you haven't already, go follow me on Instagram or
TikTok at your underscore again, Solvice. That's Jar Underscore g
O n SA l VS. I'm going to be producing
(00:49):
a TV series called Unshaming as my next career move,
where I interview people on the shame that they've overcome,
and I want you to stay in touch with me.
I read every letter you send, every message that I
get on Instagram from you, and it means a lot.
I want to say thank you for all of the
encouragement and I cannot wait to take you with me
(01:11):
on this next huge part of my journey. Thank you
so much. Now let's get into the show.
Speaker 2 (01:17):
So I had an agent. I made an appointment to
see him, and I brought the manuscript and I said, Stirling,
I made sure the door was closed. Nobody else, none
of the secretaries could here. I've written a book. It
has to be under a pen name. Nobody can know
I wrote this book. I don't know if there's a
way you can do that. I'd like to get it published.
(01:38):
I'd like you to read it. Are you willing to
read it? On that basis? And no one will ever
know that it's me? And he said okay. And the
next day he called. He said, I want to got
to published, and basically he did. This was kind of
the first one written about coming out. Everybody in the
(01:59):
whole world knew basically accept my parents.
Speaker 1 (02:10):
As a gay kid, growing up religious and in the South,
I thought being gay was the worst thing I could
ever be. Now, as a journalist, I'm trying to unlearn
that by seeking out our history, and what I've found
are people and stories full of courage, perseverance, and love.
In this episode, we'll meet Andy Tobias, the author of
(02:32):
the legendary book The Best Little Boy in the World.
We'll learn about the loneliness that he battled before coming out,
and for Andy, what he believes is the opposite of
that loneliness. For my Heart podcasts, I'm Jordan and Solves,
and this is what we loved. In my first year
(03:14):
of coming out, I read almost all the popular gay
self help books, and one of them was called The
Best Little Boy in the World. Before I even knew
what the story was about. It almost felt as if
the title of the book looked me up and down
and tore into my life story. It's about a syndrome
that so many queer people share, the idea that we
(03:38):
can deflect from our shame of being gay by overachieving.
I can overcompensate with accomplishments at school and at work
and in the gym for the fact that I don't
believe I'm truly lovable. I can compete against others and
be the best, which will give me an artificial sense
(03:58):
of self worth that I don't have on my own.
It was familiar to me because it was my story
growing up. I learned very early on that the accomplishments
my parents could brag about were like a currency for approval.
When I was thirteen, I got into one of the
most competitive high schools in my city. In college, I
(04:22):
landed one of the most competitive internships at Google, and
I won the opportunity my senior year to give the
student commencement speech at graduation. I had hoped to that
by being the best little boy in the world, the
best high schooler, the best intern, the best everything, it
would distract from my deep inner belief that I wasn't
(04:44):
worthy of love. But it didn't. It just left me
on top of a big pyramid of achievement by myself alone.
When I read the book, it gave me language for
the first time to explain this experience, and it helped
(05:05):
me realize that my accomplishments would never soothe my innate
need to be loved. My next guest, Andy Tobias, is
the author of that book, The Best Little Boy in
the World. According to Amazon, it has sold over a
million copies since it first came out in nineteen seventy
three and has never gone out of print. The book
(05:28):
has touched the lives of countless queer people across decades,
including many of my guests this season. Andy would go
on to become one of the most well known financial
thinkers in America, writing for Time, in Esquire and New
York Magazine. He's written multiple best selling books on money
and investing, and for many years was the treasurer of
(05:49):
the Democratic National Committee. But long before that, in the
fifties and sixties, when he was growing up, Andy Tobias
was also the best little boy way in the world.
What was that moment for you when you knew that
(06:12):
you were gay or different for the first time? As
a child, we.
Speaker 2 (06:16):
Went to Palm Springs. My stayed at my grandmother's place.
Who knew that Palm Springs would become a gay mecca.
And I couldn't have been eight, so I must have
been ten, and I was thumbing through a Sports Illustrated
and I saw a particular picture that, oh, wow, boxer
with us. You know, I probably somebody who had just
(06:37):
won the lightweight something or other than Sports Illustrated. But
there were stirrings' There hadn't been stirrings before that, I remember.
Speaker 1 (06:51):
So what kind of messages were you getting about being
gay in the fifties?
Speaker 2 (06:57):
So basically I was watching tea in the den up
in the country on a little black and white TV.
Because this is nineteen fifty seven and I'm ten. This
is now sixty seven years ago or almost sixty eight,
and I remember it like it was yesterday. Ben Kosovar,
who was an army buddy of my dad, comes through
with my dad and they were talking about something and
(07:18):
all they were just walking through the hallway, and the
one snippet I heard was Ben Kosovar saying, oh, he's
a homosexual. And they were gone, and I'm thinking, oh
my god, that's the word for it.
Speaker 1 (07:36):
You didn't even know what they were exactly. You didn't
hear talking about.
Speaker 2 (07:39):
Some awful person who was a queer, and which is
the worst thing you could possibly be in nineteen fifty
seven among the straight guys. My father was a wonderful,
wonderful man, my mother was a wonderful woman. But they
hated gay people because everybody did or or they you know,
they pitied them, and they it was just a horrible
horror thing to be. You didn't want to have anything
(08:02):
to do with gay people. So I knew, and from
age ten to age twenty two, I had this terrible
secret that no one could ever know. And there was
no question about it. The only issue is how am
I going to hide it for the rest of my
life and how am I going to have a life
because I probably won't be able to. I thought about
(08:24):
it constantly, especially once the hormones kicked in more or
less that year, and the next year and the year after.
So for the next twelve years, which is a long
time when you're ten, to keep this secret, and Jordan,
I thought about it constantly. I was afraid of everything,
including talking in my sleep. That was the one thing
I couldn't totally necessarily control.
Speaker 1 (08:46):
You talked about kind of this experience with your dad
and his friend in the army and understanding that that
was a bad thing to be gay. What did that
mentality sort of create for you in the next chapter
of your life.
Speaker 2 (09:04):
I spent the next twelve or thirteen years being deeply,
deeply in the closet and trying to do everything right,
trying to get the best grades I could, trying to
get my little varsity letters. I had to go to
Harvard because my brother, my older brother, Goliath, who was
four years older, almost four years, he had gone to Harvard.
I was very competitive with him in a way, I guess,
(09:25):
and so would look for any opportunity to be the
better performing child. So he would get in trouble, and
I would oh, Andy's such a good boy. And when
it was time to apply to schools, I didn't know
where to apply, and I really was very out of
it in so many ways, including this one. But my
(09:47):
parents said, well, you're applying to Harvard. What do you mean?
And I said, well, yeah, but okay, where else? They said,
what do you mean? Where else? You're applying to Harvard?
And I said, what if you don't get in? I
had to go to Harvard, and thank Heavens, I got
in because I would have been deep trouble, I guess
with the Supreme Court if I didn't.
Speaker 1 (10:06):
Well, how was it at Harvard being gay? I mean
I came out my senior year of college, and I
feel like those years were turmoil for me because it
was becoming harder and harder and harder to conceal my
sexuality and stay in the closet even to myself. What
was it like for you during those years in college?
Speaker 2 (10:30):
Well, in high school I was in love with various people,
I mean deeply in love, but couldn't do anything. And
in college I was madly in love with a whole
succession of people, none of whom ever knew. I mean
two of my roommates. One went on to be mayor
of Cincinnati, and the other roommates that I was in
love with became dean of students at the University of
(10:52):
British Columbia with sixty five thousand students, and oh my god,
college was so lonely on Saturday nights day and everybody
else would go out looking for women. Harvard was all
I pretended. I hated it, but there was all guys
and we weren't even allowed to have women in the
rooms except for it was called parietals, and the parietals
(11:12):
on weekdays.
Speaker 1 (11:12):
I think, oh, this was before it was a co ed.
Speaker 2 (11:15):
Ye. Yes, we had electricity, but we didn't have women.
So Saturday nights Arnt and Brian and the others would
go out to parties and looking for chicks and all
these things. And I would pretend that I had a
turn paper I had to do, or this or that
the other thing. I was very busy with extracurricular stuff.
But what I would really do Saturday night, I would
(11:35):
sit alone in our dorm room or our suite I
guess you call it, with the lights off. I would
listen to albums over and over again. One Johnny Mathis.
The album is called Heavenly. It is the most romatic
album you will ever hear. And I would listen to
these love songs basically they were so beautiful and the
express the yearning, the yearning and the yearning and the
(11:59):
yearning that I've felt. That's how lonely I was, and
so that really spoke to me.
Speaker 1 (12:04):
So andy. At some point in your coming out journey,
you decide to write this book, The Best Little Boy
in the World. What was that like?
Speaker 2 (12:14):
When I was twenty three, I went back to business
school basically to have something respectable to do while I
came out of the closet. I was did very little
of the homework, and I was terrible in the classroom
and all that kind of stuff. But I needed some cover.
I needed something respectable to do.
Speaker 1 (12:32):
This was another form of compensation, another form of being
the best twenty three year old boy in the world.
Speaker 2 (12:39):
You know, I was my cover story. Every night, while
I was supposed to be studying the cases, I would
get in my little eighteen hundred and eleven dollars Fiat
Spider and drive down to Sporters, which was the bar
of k bar, of course, and there were like four
bars in Boston, and this was the kind of the
collegiate one and where I might meet somebody that I like.
(13:03):
But that summer I realized, hey, this is crazy. Some
of the people I'm meeting the bar. One of them's
a priest, one of them is a cop. So after
a couple of years, when I was just finishing business school,
I'd already had some stuff in New York magazine for
other reasons, and I realized I should write about this.
(13:24):
This is an unbelievable story. There is this whole world
out there that millions of people know about, including some
straight people, mostly gay people, but straight you know, in
the theater and this and a lot of people know it,
and nobody else knows, but most of America know it,
just wasn't discussed and so on and so forth. So
(13:46):
what a book, What an opportunity to now. I was
not brave in any way, so I couldn't let anybody
know that I wrote the book. But I wrote this
book under a pen name. I remember going kind of
vibrating with nervousness and sweating. I went to my agent,
because I had a literary agent, because I had.
Speaker 1 (14:07):
This is the best little boy in the world. You
write this book.
Speaker 2 (14:10):
Yeah. Before that book, I had had a couple other books,
and I'd had articles. I was on the cover of
New York Magazine and all these kinds of things. So
I had an agent and he was such a straight
lace waspish well I can say his name is passed on,
and he was in many ways a wonderful man. His
name was Sterling Lord. I made an appointment to see
(14:30):
him and I brought the manuscript. This is before PDFs
or any of that stuff. So I had one copy.
I guess I made a xerox or something. I brought
the manuscript and I said, Sterling. I made sure the
door was closed. Nobody else, none of the secretaries could here.
I've written a book. It has to be under a
pen name. Nobody can know I wrote this book. I
(14:51):
don't know if there's a way you can do that.
I'd like to get it published. I'd like you to
read it. Are you willing to read it? On that basis?
And no one will ever know that it's me? And
he said okay. And the next day he called and
he said, I want to got to publish, And basically
he did This was kind of the first one written
(15:11):
about coming out.
Speaker 1 (15:14):
So the book comes out and it changes so many
people's lives. It's the first of its kind. But your
parents still don't know that you're gay.
Speaker 2 (15:24):
Everybody in the whole world knew, basically except my parents.
I mean, how could I tell my parents. They loved
me so much and I love them so much, and
this was a terrible thing to be And I didn't
want to, you know. And I thought it over and
over again a billion different times. When I would go up,
(15:46):
you know, get in my car, drive up to visit
them for Thanksgiving or for this time or for that time,
I would think through my head how the conversation would go,
and I would this time, I'm going to do it.
This went on for years.
Speaker 1 (16:07):
By his mid twenties, Andy had graduated from Harvard and
Harvard Business School, and he was a regular finance contributor
to New York Magazine and had even appeared on the
cover of the magazine in nineteen seventy. When he published
The Best Little Boy in the World in nineteen seventy three,
it quickly began impacting the lives of many gay men
(16:27):
across the nation. The initial printing sold thousands of copies
and quickly sold out, and Andy would receive powerful letters
from readers telling him, I can't believe you've written my story.
At a time when being gay was still very shameful,
this was deeply rewarding to him. But even though he
had a full fledged gay life with friends and fans
(16:51):
and even a few romantic relationships, he was still closeted
to his parents.
Speaker 2 (16:57):
The book had come out, it had been reviewed in
The New or Times Sunday. I had had an excerpt
of it in New York Magazine under a pen name.
But I had a friend from high school called from
California say hey, Andy, congratulations on this. You know. I said,
what do you mean, How did you know? He said, oh,
it's obvious your style. You know, it was obvious it
was you. So he knew, but my parents didn't know.
(17:18):
And this went on for years. Okay, the book came
out when I was twenty five. Everybody knew, People at
New York Magazine knew, and I would drive up to
visit my parents and go through my head. Finally, age thirty,
the paperbacks about to come out, and I just couldn't
stand it anymore. And every Sunday, I would call my
(17:41):
parents to say hi, because that's what you do. And
I called my mother picked up, and I said, Mom, listen,
I'm about to tell you something that I either should
have told you ten years ago or I should never
tell you. And this is certainly not the way to
do it over the phone. But I can't stand it anymore.
There's no good way to do it. And my mother
(18:02):
said instantly, okay, but don't tell your father. He's coming
to he's coming to the phone. And so he came
to the phone. So we talked about something else or whatever,
and then I reconnoitered with my mother and I said,
what do you mean, don't tell my father. This went
on for two years. I finally said, Mom, this is
just ridiculous. This is insane. So she said, all right,
(18:23):
I'm going to California. I'll be gone for a few days.
On Sunday, call your dad. Ask him to stop by
your apartment on the on the way in from the
country back into the city, because that's what we did,
and asked him to come by. So I did. He
came by and I basically told him and he said okay,
(18:44):
and I said, what do you mean Okay. I was
kind of expecting that this was I've been I've been
waiting her twenty years to finally and he said, well,
you know, you're not a bad looking guy. You never
bring girls home, you never have, you don't talk about
girls into I can't say I'm completely surprised. So now
I'm feeling you know, I've gone through all that. So
(19:06):
I said, would it surprise you to know I've written
a book about it that was reviewed in the New
York Times? And he said, what what? I So I
gave him the book, and now I wow. I gave
him the book, and it's hard to do the rest
of this way out getting a little choked up because
he was wonderful, wonderful man. And he called at nine
(19:26):
o'clock the next morning and he was crying. It was clear.
I said, why are you crying? He said, I stayed up.
I stayed up all night and I read it twice,
and I just feel so bad that I didn't do
anything to help you. I had great parents, so that's
how I told him. Only took me, you know, twenty
years from when I knew and five years from when
(19:49):
I wrote the book. And I guess I was thirty
two by the time I told my dad.
Speaker 1 (19:55):
The nineteen eighties were a decade of success for Andy.
He became a household name as a financial guru, but
it was also a time of unbearable loss. Andy was
living through the AIDS crisis. He was watching his best
friends get sick and die, Young brilliant men, friends he
(20:15):
had danced with at Fire Island, laughed with over intimate dinners,
friends who had become family to him disappearing one by one.
And at the time, it seemed like the presidential administrations
of Ronald Reagan and George Bush Senior were largely indifferent.
After all, AIDS was a disease shrouded in shame because
(20:38):
it largely affected queer people, a segment of society many
viewed as worthless. But when a young governor named Bill
Clinton decided to run for president, Andy and many LGBTQ
Americans felt a glimmer of hope. Bill Clinton was the
first president to appoint qualified gay Americans into his administration,
(20:59):
showing the nation that LGBTQ Americans were respectable, dignified people.
He also declared war on AIDS and made major strides
in ending the crisis, and when Clinton got elected, Andy
got the chance to tell him thank you.
Speaker 2 (21:16):
Through a series of lucky, odd coincidences, I got to
know the governor of Arkansas, very young guy, at his
very pretty.
Speaker 1 (21:22):
Wife Bill and Hillary Clinton.
Speaker 2 (21:24):
Yeah, and then he went off and got himself elected.
And on January first, nineteen ninety three, nineteen days before
he was in fact going to be inaugurated, they were
he and his wife were at the thing that where
I met him, a thing called Renaissance Weekend that about
thousand people went to, and they put me on a paddel.
They called it a panel, each one with two minutes,
(21:45):
and your assignment was New Year's Day, nineteen ninety three.
What I would say if I had two minutes to
say anything I wanted to the next president of the
United States. And then there was a big, big footnote,
don't expect him to be there. He won't necessarily be there.
I decided I didn't tell anybody. I was too scared
to tell anybody. I didn't tell any of my friends.
The people who knew me there knew I was gay.
(22:07):
I've been gay forever, but there are a lot of
people I didn't know there. But I was so scared
because eight hundred people whatever it was in the audience,
And so I got up there and I say, and
I'm looking straight at him, and I say, if I
had two minutes to say anything, you might expect me
to talk about smoking, because they knew I was a
(22:28):
big anti tobacco guy. But really, there's only one thing
I could say, which is thank you. You haven't even
taken office yet, and already you have dramatically improved my
life and the lives of millions of other gay and
lesbian people around the world. So I did my little
two minutes on that, and the response I got afterwards.
(22:48):
Remember this is nineteen ninety three, long after Snowmall much
progress had been made. But Bill clint was the very
first presidential candidate who would ever put our topic on
the national stage and who had ever done a fundraiser
with LGBT people when he was a candidate.
Speaker 1 (23:05):
And this is the backdrop of all of this, is aids.
Speaker 2 (23:09):
Yes, I lost half my friends and age they died.
Half my friends, including my partner of seven years, Scott.
Speaker 1 (23:18):
You know when you were talking about coming out to
the Clintons, it made you emotional. I wonder why that
that was such a touching moment in your life.
Speaker 2 (23:30):
A couple of weeks ago, I had the opportunity to
throw a wedding for my two best young friends. I'd
never thrown a wedding before, and I was the epiciant,
and I was going to I decided not to say
this because it was about them, not about me. But
I was thinking, as I kind of m seed the
thing I was thinking of saying. You know, a lot
of you think that I walked down here, like eight
(23:52):
blocks from south from where I live, which is true,
But really the journey started about eight blocks west and
twenty blocks north. And it's been seventy seven years, and
I get emotional because we have been through so much.
Speaker 1 (24:21):
By the late nineties, Andy had become an important voice
in Democratic politics. As the treasurer of the Democratic National Committee.
He would help prop up two wildly successful presidential campaigns
for President Obama, and at one point had become one
of the highest profile gay public officials in America. As
part of his service, in twenty thirteen, he traveled to
(24:43):
China and came out to the country's Vice president. Andy,
once a lonely gay child who hid his sexuality and shame,
had completely transformed into a global advocate for LGBT causes.
Speaker 2 (24:57):
So I got a call from Howard Dean, who had
been the governor of Vermont and had been the chair
of the Democrat National Committee, so I knew him that way.
And he said, Andy, there's this thing. Every six months
they have some Democrats and some Republicans go to China
and then every six months the Chinese Communist Party come
to Washington. I've done it twice, can't do it again.
(25:18):
You should be one of the three Democrats who goes.
It's an exchange between the parties of the United States
and the Party of China. And I said, you crazy.
I don't know anything about I don't speak.
Speaker 1 (25:30):
Chinese, I don't when was this.
Speaker 2 (25:32):
This was twenty thirteen. But after saying no, no, no,
about a million times, they finally persuaded me to do it.
And I was very nervous about it, and I was
going to have to deal with people that I didn't
know and who didn't certainly didn't know about my life.
(25:52):
And I had been asked to give the first little
remarks with the Vice President of China, and my topic
was supposed to be the you know, gridlock between the
two parties in Congress and all this stuff. I addressed
the topic, and then I said, and if I might,
as a point of personal privilege, as we call it
in the US, I explain that, you know, three of
(26:16):
the nine officers of the Democratic National Committee, including me,
were openly gay. I said, you know, they're probably about
one hundred million gay people and LGBT people in China,
and of your eighty five million Chinese Party of the
Communist Party members, do you have any sense of how many?
You know, how many are in your leadership in America?
(26:38):
He's a professor. Do we know anything about that professor? Whoever?
It was no, but we could look into him all
that anyway. Frankly, it was thrilling to me because the
goal was maybe we can show them that, you know,
this is not a big deal, because nothing to make
a hundred million people happier. Things To make somebody happier,
(27:01):
you need to build things, or you need to grow things,
or you need to you know, hurt somebody else, make
them un more or less happy. Here, you can make
one hundred million people happier just by you know, letting
them live their lives without fear of persecution. That kind
of thing.
Speaker 1 (27:19):
We've talked a little bit about this amazing life that
you've lived. Andy. As gay men, it's no secret that
we tend to chase the ideals of what we think
will make us happy, working out for hours on end
in the gym, in our body, image and sex and wealth.
(27:41):
But what has made you happy in your life?
Speaker 2 (27:46):
Chosen family. I have an amazing family of astonishing friends.
I tell my young friends, if you've got your health,
you've got your friends, you've got a good Internet connection,
and you have purpose in your life, you have everything.
I wrote a book called The Only Investment God You'll
Ever Need, you know, two hundred and whatever pages. I
(28:07):
wrote another one called The Only Relationship Guide You'll Ever Need,
which is just one sentence, so I couldn't actually publish
it as a book. But it's be nice to each
other and find humor in the compromises. They're worth it.
Friends are everything, and so that's the opposite of loneliness.
Speaker 1 (28:25):
What you're saying is it's it's community or family.
Speaker 2 (28:29):
You build your own family.
Speaker 1 (28:35):
But We Loved is hosted by me Jordan Gonsolves. If
you want to write in to tell your story, email
us at but We Loved at gmail dot com, or
you can send me a message on Instagram or TikTok
at your underscore goa and solve this. We are a
production of The Outspoken Podcast Network and iHeart Podcasts, but
(28:55):
We Loved was originally developed with Pushkin Industries. Our producers
are Joe pat Emily Meronoff, and Christina Loranger. Our executive
producers are me Maya Howard and Katrina Norville. Original music
by Steve Boone. Special thanks to Jay Bronson and Roquel Willis.
If you loved this episode, leave us a rating and
(29:17):
follow us on Apple Podcasts and Spotify, and thank you
for listening.
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