EPISODE:
12
|
December 11, 2025

How Jessica Shepherd, MD Is Rebuilding Healthcare From the Inside

Featuring
Jessica Shepherd, MD

What happens when a doctor refuses to accept the limits of a broken system? In this episode of Less Than One Percent, Jessica Shepherd, MD, OBGYN, author of Generation M, and a nationally recognized female leader shaping the future of women’s health, sits down with host Imamu Tomlinson, MD for a raw conversation about representation in medicine.

As Chief Medical Officer at Hers, she’s redefining how telehealth platforms and telehealth services can close the gaps in access, dignity, and trust, especially for women.

Together, Dr. Shepherd and Mu dive into why breaking norms isn’t optional. It’s necessary.

This is how Jessica Shepherd, MD disrupted women’s health care with humility.

Also listen on:

Timestamps

1:00 – Meet Jessica Shepherd, MD

7:30 – Embracing her Jamaican heritage

11:00 – Who Jessica Shepherd, MD is today

17:01 – There is power in connection

19:03 – The vision for Hers

23:00 – What makes Jessica Shepherd, MD unique

25:50 – Generation M book

28:00 – Closing thoughts: This is just the beginning

Transcript

1:00
Meet Jessica Shepherd, MD

1:00

All right, welcome to Less than 1%. Um,

1:07

I know I I apologize. I'm wearing a

1:10

jacket. Don't judge me. I'm at an

1:12

amazing event. I'm here at Brilliance uh

1:14

2025. It's a, you know, conference

1:17

that's really empowering women. And I'm

1:20

cheating because I shouldn't be doing a

1:22

podcast because I'm not doing in my

1:24

studio and we have a different setup.

1:27

But I have the amazing Jessica Sheepard.

1:30

Good.

1:30

I mean, I I am just I'm just like beside

1:34

myself that you're here.

1:36

I'm here present

1:37

because you are all over the place.

1:40

Yeah.

1:40

I So explain to me when did you start at

1:43

Hims and Hers? Because you were Is that

1:45

a recent?

1:46

It is very recent. I'm just actually

1:48

just passing a year

1:50

at hers and you know it it really came

1:53

at a time where things were already like

1:55

chaotic and hectic. I was in the middle

1:56

of my book launch last year in October

2:00

and you know I have a my own practice.

2:02

It's it's a smaller practice because I

2:05

have been doing so much as far as

2:06

consulting and previous to hers I was a

2:09

chief medical officer at very well. So,

2:11

I've always had like, you know, a

2:13

million things going on. And so, when

2:15

the book came out, you know, that tour

2:17

took a lot out of me. And,

2:19

you know, I had to obviously not see

2:21

patients during that time. I was doing I

2:24

think we did 16 cities during that tour,

2:26

all the while on boarding to hers.

2:29

So, here we are a year later and um I'm

2:32

proud of the work that we've done as a

2:34

team. But, like you saying, like looking

2:36

back, you're like,

2:37

what is going on? People often ask me

2:39

that. I'm like, I'm not sure, but I'm

2:40

just here.

2:41

It's funny like, you know, wherever I

2:43

was I love Charlene Lee that get gave an

2:46

answer on balance.

2:47

Yeah.

2:48

Because I don't believe I mean I I agree

2:50

with there's no balance. You just kind

2:51

of do everything and when you're

2:52

present,

2:53

you're present.

2:53

You're the most amazing. It's the most

2:55

amazing time ever.

2:56

Yeah.

2:56

Um but you know, I have to go there and

2:59

I normally I wait

3:00

and I want to talk about what you do at

3:02

Hers. I want to talk about that, but I

3:04

have to go back

3:05

cuz we because we are not from Toronto.

3:09

We're both from Toronto. We're from Toronto. That's how you know

3:12

if someone's from Toronto

3:14

now. And actually, people from Toronto

3:16

don't say Toronto when you ask them

3:19

where they're from,

3:19

right?

3:20

So, officially, where are you from?

3:22

I'm from Scar Bro.

3:24

This is This is

3:26

right from Scar Bro. Malvin.

3:28

No, no, no. You're not from Malvin. I

3:29

am. There's no way.

3:31

Absolutely. So now we're going to go

3:33

even to what elementary or high school

3:35

did you go to?

3:35

Okay, so this is this is crazy. So I

3:38

actually went to Raybuff.

3:40

I went to St. Columba and then Sacred

3:42

Heart

3:43

because my parents didn't want me to go

3:45

to Pope John Paul which had just opened

3:47

because I really wanted to go to Mother

3:48

Teresa.

3:49

That's where my sister went.

3:51

We were walking distance from Mother

3:52

Teresa and I ended up going to Pearson.

3:55

Wow.

3:56

Insane. Literally the same neighborhood.

3:57

Yeah. So I was at I was at Morningside.

4:00

Morningside and Elmer, but I was at it

4:01

was in it was in that neighborhood right

4:03

next to Pope John Paul.

4:04

I was at Morningside and in between

4:06

Finch and Shepard.

4:08

So, you know, because I I used to go to

4:10

uh Mr. Jerk right there.

4:12

Yes.

4:13

This is This is

4:14

We're from literally the same

4:15

neighborhood.

4:16

Same place. So,

4:18

my parents will not I know you I know

4:21

you're watching, Mom.

4:22

My parents will not let me say that I'm

4:25

from Malvin. And I'm like, yo,

4:27

Melvin represents

4:28

it is Malvin. Like it's this pocket, but

4:32

it's still Malvin.

4:33

Yeah,

4:34

that's amazing. How are we from the same

4:35

place?

4:36

Isn't that insane? I really think, you

4:38

know,

4:39

looking back at the neighborhood we grew

4:41

up in and and also the country,

4:43

there's so much richness in

4:46

that kind of soil that we grew up in.

4:49

And I find this anytime I, you know, in

4:51

my travels meet someone who's from not

4:54

only Canada, but from Toronto and then

4:55

narrowing it down to Scar Bro, Melvin,

4:57

it's it's amazing. I'm so grateful and

5:00

proud to have grown up there.

5:02

Absolutely. So So you um

5:06

I have all these questions that that

5:08

we we shouldn't record.

5:09

We're we're we're gonna this podcast is

5:11

going to turn into a twohour

5:13

Yeah. You're miss your flight. You miss

5:14

flight. Um, so no, I I totally agree

5:17

with you because I think that I always

5:19

tell people the upbringing that I had

5:22

was very different. I I mean I Jamaican

5:24

family.

5:24

Yeah.

5:25

Jamaican parents. Yeah. So it's like

5:28

I didn't really like even people talked

5:30

about

5:32

uh you know just in America you identify

5:34

with your race.

5:36

In Canada you identify with your

5:38

culture.

5:39

I said this just last week. I said when

5:42

you ask someone

5:44

um from Toronto or Scarbor or Malvin,

5:47

we don't say we say where are you from.

5:50

Yeah.

5:50

And you identify with your culture.

5:53

Yes.

5:54

And you're very proud of like whatever

5:57

little island you're from or whatever

5:58

country you're from. you know, I don't

6:00

it was very hard for me, you know,

6:02

moving to the US in asking those same

6:04

questions and people be like offended as

6:06

if

6:07

I was trying to uh maybe ostracize, but

6:11

it's we were so proud of where you are

6:13

and I think that kind of transpired into

6:16

the the fabric and the DNA of who I am

6:18

and and I love that.

6:20

So again, Drake,

6:22

it's not just it's actually T dot. We

6:24

know that we grew up saying T dot and I

6:28

will share something uh vulnerable.

6:31

Uhhuh.

6:31

So

6:32

we're doing vulnerability now.

6:33

I was uh I was I was rapping.

6:37

Really?

6:38

I was rapping. So I got uh I almost I we

6:42

had a contract with Arista. I was

6:43

talking with my guy last night who was

6:44

my manager.

6:46

Are you kidding me?

6:47

Yeah. I was I was running around all

6:50

over Toronto rapping and um Yeah. That's

6:54

uh so then

6:56

so we're going to have at the end of

6:57

this particular session we're going to

6:59

have you do a

7:00

you know what's funny? Yeah.

7:01

No. So I stopped I kind of stopped but

7:02

today I I found a just a random song in

7:06

the airport. You know they play stuff

7:08

overhead. I'm like that's that's

7:10

amazing. I listen and then I started

7:12

because I was wired at 3:00 in the

7:14

morning to come here.

7:15

Yeah.

7:15

And I started writing lyrics. I'm like

7:18

okay.

7:18

See it's a comeback. We're making a

7:20

comeback here. What are you doing? What

7:21

are you doing? Okay. So I want to jump

7:24

to so Jamaican heritage too.

7:26

Jamaican heritage both parents.

7:28

Both parents.

7:28

Yes.

7:30
Embracing her Jamaican heritage

7:30

Yeah. I mean so um everybody safe uh

7:34

extended family from

7:35

so a little displaced you know but still

7:38

safe.

7:38

Where where in Jamaica?

7:39

So my mom's from Mapen. Okay. And my dad

7:41

is basically from Kingston. Okay. And

7:43

then my mom went to high school in

7:45

Kingston and that's where they met.

7:46

So we're Graange Hill.

7:48

Yeah.

7:48

Um and well my dad's from Graange Hill

7:50

Country Guy.

7:51

Uhhuh. And then my mom is from she

7:54

really is from kind of from Kingston.

7:56

Yeah.

7:56

You know, went to went to boarding

7:58

school.

8:00

Um but yeah, the house in Green Hill,

8:02

the family house is probably gone. We

8:03

haven't heard yet, but right

8:06

Western Jamaica.

8:08

So that's that's amazing. And do you

8:10

think that that Jamaican heritage,

8:12

you know, filtered through Canada

8:15

and then filtered again through America?

8:18

Yeah.

8:19

It's it it seems to be different. Do you

8:21

feel different? I mean, is there

8:22

something

8:23

I would definitely say that you don't

8:26

sometimes realize um the things that

8:28

have kind of shaped you until you're put

8:30

in positions

8:32

that maybe either make it very magnified

8:35

or try to lessen it.

8:37

And I feel, you know, for how I grew up

8:40

and where I grew up, uh moving when I

8:42

was 14, you know, I had just finished

8:44

grade nine,

8:45

so I'd already started the high school

8:47

kind of transition.

8:48

Yeah. Moving to the US was very

8:51

difficult especially not only did we

8:54

move to the US, we moved to Oklahoma.

8:56

Oh man.

8:57

So imagine already now moving countries

9:00

but also to nothing.

9:01

Yeah.

9:02

And so the identity factor of who I was

9:05

and where I belonged especially during

9:07

the teenage years was very hard. And I'm

9:11

glad that I had the strength, I guess

9:13

you can say, or the vitality of, you

9:16

know, when you're representing Jamaica

9:19

in, you know, in your basement party or

9:21

at your high school, that that really

9:25

shone through because I was like, I am

9:27

Jamaican.

9:28

Yeah.

9:28

And you have pride with it. And so,

9:31

you know, it's almost like you're like

9:32

in the midst of like what is going on?

9:34

and you're like in a business,

9:36

you know? So, all those things come to

9:38

come to play when you're like, I know

9:40

who I am. I'm in a business.

9:42

Everything happens for a reason. This is

9:45

this is one of the best days of my life

9:46

right here.

9:47

It's so funny.

9:49

I um so I I did the opport

9:56

and uh yeah, culture shock, a lot of

9:59

culture shock because

10:01

um I didn't understand things. I I I

10:04

tell this to a bunch of different

10:05

people. I went I was on campus

10:07

and upstate New York is not very

10:09

diverse.

10:10

Not at all.

10:10

And so three three black students start

10:13

running towards me and I'm like, "Okay,

10:16

you know, I'm from Malvin, you know, I'm

10:18

ready. I'm ready."

10:19

Exactly. Yeah.

10:20

And they run up to me and they're then I

10:21

seem closer and they're all laughing and

10:23

smiling. They're cheering and they're

10:25

like, "Hey, you need to join the Black

10:26

Student Union."

10:28

And I was like, "Why?"

10:30

You know what I mean? Because

10:31

I mean, you know, we dealt with racism

10:34

and stereotypes,

10:36

but I think having that, to your point,

10:38

having that Jamaicanness or frankly that

10:41

Italian or, you know, Toronto's really

10:44

cosmopolitan. So,

10:45

everyone had a very strong understanding

10:47

of who they were.

10:48

So, there was no there was no

10:49

inferiority no uh associated with it,

10:52

you know. But anyway,

10:54

let's let's talk about um

10:57

I want to talk about what you do now

10:59

because you

11:01

you are representing.

11:00
Who Jessica Shepherd, MD is today

11:00

I mean you're amazing because you're not

11:06

only representing um hers I mean you're

11:10

representing me you're representing my

11:11

daughter you're representing there are a

11:13

lot of different

11:14

you know sort of for lack of better word

11:16

boxes that you check that let people

11:19

know wow this is

11:21

you know hers obviously is committed to

11:23

diversity yeah

11:24

um and put you in position but then you

11:26

also taken that and elevated it

11:29

yeah I believe we have to and I when I

11:32

say we exactly who you were saying is

11:35

for all those boxes that are checked

11:38

that means in every box that's checked

11:40

there's a community of people behind

11:42

that and so I feel it's like my utmost

11:45

responsibility is right right what

11:47

you're given means that you have

11:49

responsibility to show up

11:52

that duty

11:53

it's it's you show up and and it's a big

11:55

you know ticket to fill but I believe in

11:59

the path that you were given prior to

12:01

that. You can either own it and lean

12:03

into it or shy away from it. And I think

12:07

very early I realized, you know, always

12:10

wanted to be a doctor. It's a very like

12:12

boring story. Yeah.

12:13

Like in grade four, what do you want to

12:15

be? I literally said an OBGYn.

12:17

So there's no like there's no creativity

12:19

to my journey. I was just like, oh, I

12:21

ended up being a doctor. So people are

12:22

like that's great. I'm like it's a

12:23

boring story. So now I've actually come

12:25

up with another story that I was in a

12:26

rock band and then I was like a air

12:29

pilot and then finally went to medicine.

12:30

Sounds better.

12:31

Yeah.

12:31

But even in getting to that was

12:35

difficulty, right?

12:36

So you know being black, being female, I

12:40

really didn't have a great support

12:43

system in understanding how to achieve

12:45

to become a doctor. I was just like,

12:47

"All right, here we go." And it's like

12:49

being consistently fed by like a fire

12:52

hose.

12:52

Yeah. And so you get through that and

12:55

then you're like I made it and for 15

12:58

years I was in academics. I did a

13:00

fellowship in surgery. So I did another

13:02

two years after residency and then I was

13:04

like

13:04

because you like punishment because I

13:05

was just about to say fellowship

13:08

fellowship and then while I was doing my

13:09

surgical fellowship at the University of

13:11

Louisville that's when I got my MBA and

13:14

so I was like surgeon by day MBA student

13:17

by night for two years straight.

13:19

Wow. But I knew I was like, I'm

13:21

presented with this opportunity and I

13:23

can do my MBA so do it. Going into

13:26

academics for 15 years and then being

13:29

presented with the opportunity to now go

13:31

corporate and consult. It was it really

13:34

was something that I in my head I knew I

13:37

wanted to do, but putting it into the

13:39

universe and then actually getting the

13:41

opportunity

13:42

has like I I sometimes I do look back

13:45

and I'm like, "Wow, how how did I get

13:47

here and and what happened?"

13:49

It's almost like it's so amazing. You're

13:51

like, "No, it's it's not real."

13:52

Yeah. Sometimes I do feel it's not real.

13:54

You um so you talked a little bit about

13:58

on stage you mentioned,

14:00

have you so you seem you seem outwardly

14:03

like you're on top of the world like you

14:06

I mean I mean I I got two hours sleep

14:11

last night

14:12

right and you don't know I mean I don't

14:14

know how many hours like everywhere I

14:16

see you you are absolutely on point

14:19

is there t are there times where inside

14:22

you're not on point and you're like I'm

14:23

just

14:25

I'm struggling

14:25

yes I think that for a lot of what

14:28

people see right I always say that how

14:30

people see me as the highlight reel and

14:31

it has a very big part of my everyday

14:33

life. But there are moments and even you

14:37

know like in my professional and

14:39

personal life over the last few years

14:41

I've had to sit and deal with some hard

14:44

14:44

Yeah.

14:45

And in that I would say again is another

14:47

part of the process. And that's why I

14:49

was saying today that our journeys are

14:51

not linear.

14:52

And I think in the last few years has

14:54

proven to me that it's not linear and

14:57

there are going to be some hard moments.

14:59

And that's why I've had to really do an

15:01

internal look at

15:03

what does this all mean and how are you

15:05

subscribing to what's happening

15:07

and not numbing to it and kind of just

15:09

like I'm just going to kind of distract

15:12

myself and move on and keep doing this

15:14

is actually going back to those things

15:17

that present

15:18

and being like I have to deal with these

15:20

and that takes again self-awareness one

15:23

of my biggest words for 2025

15:25

and also how do I navigate the things

15:29

that in my past have happened to me that

15:31

I'm are now revealing itself that are

15:33

not working for me. How do I how do I do

15:36

that? That's not easy work, but it's so

15:39

worth it.

15:40

And that's what I think has kind of um

15:42

created a different chapter of how I

15:44

deal with the hard moments.

15:45

Well, you're doing amazing. I mean,

15:46

you're doing you're doing amazing

15:48

things. By the way, I did have a try out

15:50

for the Canadian national team at

15:52

Pearson.

15:52

Stop.

15:53

Yeah. Yeah. Because you know Yeah. at

15:55

Pearson

15:56

and uh I know I know a bunch of those

15:59

guys.

16:00

There were a there were a few years

16:02

where Pearson basketball team

16:04

Yeah. Yeah. No, they're solid.

16:05

It was solid. I mean, the only thing

16:07

that's that helped us was that some of

16:10

the guys would always get in trouble.

16:12

Yes. Pearson was

16:14

I used to get my haircut right across

16:15

the road at that barber shop um next to

16:19

next to Max. I know exactly where you're

16:21

talking about because the next shop was

16:23

it was two crews. Two crew something.

16:25

There was a fish and chips stop right

16:27

there in a patty shop. What is going on

16:30

right now?

16:30

And I used to live uh for a while

16:33

before we moved to Morningside. I used

16:35

to live on Cro Crot Trail.

16:36

Stop.

16:37

That's right. You know

16:38

cuz Crow Trail is right by St. Columba.

16:40

So I know I know exactly where you're

16:41

speaking.

16:42

Okay. Something I ask everybody.

16:43

Yes.

16:44

Is okay. So I I I have this thing where

16:47

I talk about people's superpowers. I

16:49

didn't mention it today

16:50

because I didn't want to detract from

16:52

all of you, right? I mean, people didn't

16:53

come near me.

16:54

They did.

16:55

Um, but I I always say that when you are

16:58

doing amazing things in the world,

17:00

you're using your superpower.

17:01
There is power in connection

17:01

So for a long time in this role, I kind of got

17:04

the job, maybe I'll thought I was right,

17:07

but I didn't necessarily think I was

17:09

right.

17:09

And I was trying to fit a box. I was

17:11

trying to fit a mold in first two or

17:13

three years. wasn't like I didn't even

17:15

wear a jacket that fit right cuz I was

17:17

like, you know, I didn't even know who I

17:18

was.

17:19

Yeah.

17:19

And then once I identified what I

17:21

thought my superpower was, it's like the

17:24

organization did better. I felt better.

17:27

I was just at ease. I was just being

17:29

myself.

17:30

So, what would you say your superpower

17:31

is? And it can't be I'm on time. It

17:34

can't be, you know, something just

17:37

rudimentary. It has to be something at

17:38

your core. And when you do, when you

17:41

have when you're exhibiting that

17:42

superpower,

17:43

there's no loss of energy.

17:46

I would definitely say is the superpower

17:48

of connection.

17:50

Um, and connection doesn't necessarily

17:52

mean someone gets along with you. It

17:55

means that you get someone, right? And

17:57

you're allowing for a space for people

18:00

to showcase who they are and not always

18:04

trying to overrun that or tell someone

18:06

what they should or should not be is the

18:08

connection. So, it's that space and time

18:12

where you have maybe a moment and

18:15

connection can be I made a connection

18:16

with you in 10 seconds versus I've known

18:19

you for 2 years, 10 years. And I think

18:22

versus we both grew up in Melvin and

18:23

just didn't know each other,

18:24

right? And we didn't know each other.

18:26

But I I really feel that that's, you

18:29

know, as we progress in technology and

18:30

innovation,

18:32

sometimes we lose connection, the human

18:34

side of connection. And I think that

18:36

that there the superpower to that

18:39

is allow us to show the diversity of

18:41

showing up as different people,

18:43

different backgrounds. And I think that

18:45

goes again to where we grew up.

18:48

Yeah.

18:48

That's what I learned and that's what I

18:50

learned really to do well is to connect

18:52

with different people, different

18:54

ethnicities, etc.

18:55

Um, hers.

18:57

Yeah. What what's your I you're you're

19:01

you have you seem to have a vision for

19:03

her.

19:03
The vision for Hers

19:03

So when I see you speak about it,

19:05

you're not you're not just talking, you

19:08

know, this this isn't strategic plan

19:11

regurgitation.

19:12

There's something in your core that

19:14

you are trying to bring this company to

19:17

another level. Yeah. What what is Am I

19:20

sensing that correctly?

19:21

So yeah, you were sensing that exactly

19:23

as how I one was brought into the team.

19:25

And I think the CEO is very visionary in

19:28

how he has brought this teleaalth

19:31

platform

19:32

that started off with him and then hers

19:34

came a year later. So that's eight years

19:36

ago is that there is something there's a

19:39

big gap in healthcare and we spoke about

19:41

it today as there it's broken. So it's

19:44

broken from the aspect of access and

19:47

resources, right? And that's what we

19:49

know categorically has impacted the

19:53

breakdown of healthcare are mainly those

19:55

two things among others. So now bringing

19:58

me into hers is I have seen and been a

20:02

part of that traditional health care

20:04

setting where I do know what is lacking.

20:07

Yeah.

20:07

So now we you can say like on the other

20:09

side of the pendulum is technology at

20:11

its finest, right? But still with that

20:14

you can have some kind of obscurities

20:17

that you're not visualizing. So how do

20:20

we bridge that? How do we allow

20:23

teleaalth to have compassion? How do we

20:26

allow teleaalth to allow women to feel

20:29

heard and seen? Yeah. which sounds weird

20:32

because it's tellalth but in traditional

20:35

health care setting we've had that for

20:37

centuries but still there's something

20:38

missing when it comes to do I feel seen

20:41

and heard and so I I do feel that now

20:44

that I've experienced both

20:46

I have that ability to create an overlay

20:50

of the brilliance of technology and

20:52

innovation to something that

20:54

fundamentally when you think about

20:55

medicine where it started was you know

20:57

the community doctor who would go see

20:59

everyone but what do they have on the

21:01

wall.

21:02

They have connection. They allow people

21:03

to feel seen and heard. And they deliver

21:06

a system or a service that is ultimately

21:10

going to help impact and shape people's

21:12

lives.

21:14

Wow. That's that's that's impressive.

21:15

And I think, you know, if you look at it

21:17

and we watched we watched, you know,

21:19

we've watched him and now hers grow.

21:23

Yeah.

21:23

And you know, we have a whole

21:25

we have a whole uh

21:26

you know, sort of innovation wing. We

21:28

spin up small companies and we're trying

21:30

to do all this stuff and I think you

21:31

guys really cornered the market cornered

21:35

is the right word on

21:38

just really what is going to be a

21:40

generational change.

21:41

It is and I think that that's where

21:43

traditional medicine is not uh catching

21:45

up.

21:45

Yes.

21:46

Is again it's it's when it's a glaring

21:48

um something that's obvious and glaring

21:51

that is missing instead of I said this

21:53

earlier instead of shying away from it

21:54

leaning into it.

21:55

Right. But there's a there is this kind

21:58

of like ego. Everyone has ego, right?

22:00

But when you let ego overtake the actual

22:02

thing that is now hindering you and not

22:05

leaning into it, that's what we're

22:06

seeing right now. And I I really just

22:09

have a strong insight for

22:13

we are we are ever evolving in society

22:16

and innovation technology is not going

22:18

anywhere.

22:19

It's only bettering by the day.

22:21

Yeah. And so if we don't find a way to

22:24

connect to humans through technology and

22:27

innovation and allow access and resource

22:29

to be some prime stakeholders in

22:32

healthcare, we are only going to

22:33

continue the same thing that we've been

22:35

doing for the last

22:35

Yeah. It's going to be Yeah. My line.

22:37

Get better faster than everybody else is

22:38

getting better so you don't get worse.

22:39

That's not transformational.

22:40

No.

22:41

So you um so we have two two more

22:44

questions. One I want to I want to talk

22:45

about the book. Yeah. uh because I think

22:48

it's important to get that information

22:49

out there. But you speak all the time.

22:53

You've been on lots of podcasts. You've

22:55

been on Good Morning America. And I'm

22:57

mad y'all didn't invite me. But if y'all

23:00

out there, I know I know I don't have

23:02

the you know, but I'm.

23:00
What makes Jessica Shepherd, MD unique

23:00

Anyway, but uh

23:06

what's something that you would want to

23:08

tell people? Because you know the whole

23:10

my whole thing with less than 1%. You're

23:12

less than 1enter by definition. And the

23:14

definition is basically that you've

23:17

achieved maybe what you didn't even

23:19

think you could achieve, right? Because

23:21

of whatever people are telling you, the

23:22

boxes that they put us in and you know

23:24

through medical school, even before

23:26

medical all that stuff. And so you're

23:28

100% a less than 1enter. But what about

23:30

you?

23:32

And I want less than 1% to have the only

23:36

the only uh you know u you know caption

23:41

of you telling us what is that what is

23:43

something that you don't want to tell

23:45

anybody else

23:47

and I mean

23:48

a good one

23:49

what what is something that

23:51

you know maybe you try to keep at bay

23:55

not talk about

23:56

I would definitely say in the space and

23:59

I'm glad you framed it that way because

24:00

I always I don't look at it like that

24:02

that I'm a less than 1enter. So

24:04

sometimes even when I hear that

24:06

is the humility behind it.

24:08

Because what I can tell you is as you

24:10

start to climb, as you're offered more

24:12

opportunities,

24:13

our mind is something that can take us

24:17

very far from where we should be

24:19

or keep it close. And sometimes in these

24:22

circles or on these platforms, you have

24:25

a very good high probability and chance

24:29

of becoming someone who maybe later you

24:31

may not want to be.

24:32

So I would say humility is one of those

24:34

things that I keep close to myself and

24:37

maybe don't want to tell everyone but

24:39

humility is something that will keep

24:41

safeguard

24:42

any you hold grudges. So I will tell

24:45

you. So as you said that I literally

24:48

I had to my internal self. I am a

24:51

Sagittarius and I I man I could hold

24:54

grudges from people in elementary school

24:56

today if I could.

24:57

But I have learned in the new version of

25:00

myself in these last two years that in

25:03

my personal journey that grudges were

25:05

not uh doing me any benefit to my

25:08

internal self. Right? And so letting go

25:11

of that is very hard. And what comes

25:13

with it, and if my sister is watching

25:15

this, she's going to gasp, is empathy,

25:17

but also compassion. I have a hard one

25:20

with that. But compassion is something

25:22

that allows me to look at grudges

25:24

differently.

25:25

Yeah. My my problem is is that that it

25:27

fuels me. So I remember everybody's

25:29

But wait, we're Jamaican. Grudgeolding

25:31

is like a sport.

25:32

Yeah.

25:33

It is a sport. So yeah, that's what

25:35

that's the br I come from is you hold a

25:38

grudge. I can hold a grudge. For sure.

25:40

For sure. Um, okay. So, let's let's talk

25:43

about the book Generation M.

25:45

Great title.

25:46

Yeah.

25:47

Much better cover than mine.

25:50
Generation M book

25:50

Uh, I'll just say mine is more austere

25:52

and trying to shock you, but yours is a

25:54

good shock factor.

25:55

But you you there's there's emotion I

25:58

think that comes just from the cover and

26:00

the title. So, tell me tell me

26:02

tell me more about that. How did you

26:05

decide to write it?

26:06

Yeah. Yeah. And and what what what what

26:08

difference are you trying to make in the

26:09

world?

26:10

Yeah. Difference in the world is the

26:12

complete composite of our lives as

26:14

women, right? So, generation M, which I

26:16

fought both for the title and the cover

26:18

from the from the book company is

26:21

because I wanted Generation M to feel

26:22

like some everyone could be a part of

26:24

it, inclusivity. And I also wanted to

26:26

not feel stigmatized because menopause

26:28

holds a lot of stigma. So, I was like,

26:30

generation M, I want to be part of it.

26:31

Create some FOMO. I wanted it to look as

26:34

if it could live anywhere and it not be

26:37

like plagued with the word menopause.

26:39

Yes.

26:39

And the last thing that I would say

26:41

about the book is it says living well in

26:42

pmenopause and menopause. I am a firm

26:44

believer. I am a big longevity doctor. I

26:48

believe in what we do for our lives now

26:50

shows up later. And I think in midlife

26:53

women are not steered in the right

26:54

direction with their health. And that's

26:56

why we do live longer years but in

26:57

poorer health. So I wanted to put in

26:59

there I talk about diet, exercise, sex,

27:02

sleeping because that's all of our

27:04

lives. And so if we don't approach it

27:06

that way, we will just be kind of tunnel

27:08

visioned into menopause and then be like

27:10

scared of it. It is something beautiful.

27:12

It is something that can create that

27:14

next 40 years of our life to be

27:17

not even transactional but

27:19

transformational. And I don't want women

27:21

to just strive to be better. I want them

27:23

to to really thrive.

27:25

Yeah. I um that I'm gonna go I'm gonna

27:28

I'm gonna get you to sign a book for me

27:29

today. I will. But then I'm still gonna

27:31

buy a book because I know how I know the

27:33

whole book selling thing is well also um

27:35

sign a book for you. Um you know,

27:38

appreciate it. I think Do we have a Do

27:40

you have a pen here? Let's see if we can

27:42

uh get Marker.

27:44

Yeah, marker's perfect.

27:45

Um but you know, I just really

27:47

appreciate you coming. Yeah.

27:49

Oh, that's great.

27:50

I really appreciate you coming. Um I

27:52

know how valuable your time is. I'm I

27:54

mean what I will say is I am glad that I

27:57

I believe that things in the universe

27:58

happen the way they are supposed to.

28:00
Closing thoughts: This is just the beginning

28:00

I'm so glad I am here and that we've had

28:02

time together and this is just the

28:04

beginning. That's what I would say. This

28:05

is just the beginning

28:05

because I think we have I you know and I

28:08

think

28:09

longevity is something that we're going

28:11

into hard and we can we can have another

28:13

conversation. But thank you so much. I I

28:15

want you to record this because I want

28:17

Yes.

28:17

I want to I want to sign

28:19

I want to sign.

28:20

You sign?

28:21

No. No, no, no. I What you need? I got

28:23

my mark

28:24

I got my own white pen because of my

28:27

black

28:27

Oh.

28:29

Yes.

28:30

So,

28:32

we got to get you uh we got to get you

28:34

um

28:40

get you on your plane.

28:41

We're going to make sure we do this on

28:43

camera.

28:43

Okay.

28:44

Got the exchange.

28:46

Perfect.

28:47

Awesome. Awesome. That's amazing.

28:50

That's amazing.

28:50

Thank you so much. I like this is this

28:54

is near and dear to my heart. You know,

28:55

as much as I travel and talk,

28:57

there are few moments that were again

28:58

the connection

29:00

like where the connection is a big part

29:02

of the event.

29:02

And what's crazy about it is that I I do

29:05

believe everything else.

29:06

Yeah.

Key Takeaways

  1. Real change happens when people feel seen, heard, and valued.
  2. Success is about facing hard moments with self-awareness and choosing growth anyway.
  3. True leadership is rooted in connection and humility, not ego.

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Episode Guests

Jessica Shepherd, MD

Dr. Jessica Shepherd, MD, MBA, FACOG, is a board-certified OB/GYN and a leading voice in women’s health and longevity. As a wife, mother, author, CEO, and media personality on her own perimenopause journey, she brings personal insight and professional expertise to her mission of empowering women through every stage of life.

As the founder of Sanctum Med + Wellness, Dr. Shepherd combines traditional and alternative medicine to provide comprehensive, holistic care. Her approach addresses the physical, emotional, and lifestyle needs of women, helping them thrive during menopause and beyond.

Dr. Shepherd’s influence reaches far beyond her practice. A sought-after voice in the media, she shares her insights as a regular on-air contributor on Good Morning America and has been featured on The Today Show, LIVE with Kelly and Mark, CNN, and Dr. Oz. Her expertise appears in Vogue, Cosmopolitan, ESSENCE, and Forbes, establishing her as a trusted voice in women’s health.

With a commitment to addressing health disparities, Dr. Shepherd now serves as Chief Medical Officer of Hers, leading efforts to expand accessible, personalized care for women. Through her work and advocacy, Dr. Shepherd continues to build a community where women are informed, supported, and empowered to live long and live well.  

For more on Jessica Shepherd, MD and her work, check out: https://www.jessicashepherdmd.com/modern-meno-community