TThe Diary of a CEO
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05 May 2025

The Woman That Makes Millionaires: They're Lying About Work Life Balance! I Built SKIMS Without Fashion Knowledge!

8Frameworks
13Insights

Frameworks in this episode

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 1

Hot Take29:00

Grede's Uncompromising View of Work-Life Balance

Grede argues that ordinary jobs should allow people to live well without routinely working evenings and weekends, while extraordinary professional ambition usually demands extraordinary effort. She frames personal logistics as the employee's responsibility within a flexible workplace; this is her leadership philosophy, not an established universal rule.

  • Grede says her workplaces allow ordinary personal appointments and flexibility
  • She distinguishes a good life from pursuing exceptional public or business success
  • She believes higher ambition often requires more availability and effort
  • She places responsibility for personal arrangements primarily on the individual
  • Her position reflects her experience and values rather than evidence that all successful people work this way

Should you be able to do that without working evenings and weekends and putting all of the hours in? Yeah, I really think that you…

Emma Grede · 36:00

if you are leading an extraordinary life, to think that extraordinary effort wouldn't be coupled to that somehow is crazy

Emma Grede · 36:00
#work-life balance#ambition#leadership#work

Explainer· 2

Explainer1:06:00

Why Good American Did Not Depend on Cheap Social Ads

Grede says early Facebook and Instagram economics gave digitally native brands a temporary customer-acquisition advantage. She credits experienced board members with pushing Good American toward profitability and additional channels, including stores and wholesale, before that favourable period ended.

  • Grede describes early social customer acquisition as an arbitrage that later diminished
  • Some advisers urged rapid spending without prioritising profitability
  • Experienced board members argued for a business that would work after the channel changed
  • The company developed stores and wholesale rather than relying only on digital acquisition
  • Grede says this broader foundation buffered the later decline

You need a profitable business that works when this is over.

Emma Grede · 1:07:30

we never rested on that being the only way that we could meet customers

Emma Grede · 1:07:30
#customer acquisition#profitability#retail#channels
Explainer1:18:00

How Grede Separates Intuition From Excitement

Grede says repeated experience helped her trust intuition, but she distinguishes an emotionally grounded conviction from excitement about apparent financial upside. She reports that investments driven mainly by the latter have not worked for her, presenting this as personal decision experience rather than a universal diagnostic.

  • Successful past decisions helped Grede build trust in her judgment
  • She distinguishes emotional resonance from general enthusiasm
  • Apparent financial upside can create excitement without deeper conviction
  • Shark Tank required her to make that distinction quickly
  • Her test is subjective and should not replace evidence or due diligence

you've got to know the difference between having intuition and a gut feeling and then just sort of general excitement

Emma Grede · 1:18:30

are you moving me emotionally or am I just like oh that feels like money over there

Emma Grede · 1:19:00
#intuition#decisions#investing#emotion

Story· 5

Story02:00

How Early Responsibility Shaped Emma Grede

Grede describes growing up in East London as the eldest of four daughters raised by a single mother. She says preparing lunches, getting her sisters to school, and worrying about unpaid bills made her responsible and protective early, while also showing her how she did not want to live.

  • Grede took on substantial care for her younger sisters
  • Financial anxiety was visible to her as a child
  • She connects that upbringing with responsibility and empathy
  • Fashion initially represented escape and possibility

I think so much of who I am and how I feel about who I am comes from where I'm from.

Emma Grede · 02:30

I think that that made me super responsible at an early age

Emma Grede · 04:30
#childhood#responsibility#family#ambition
Story43:30

The Downsizing That Changed Grede's Leadership

Grede recalls dismissing 15 people from a roughly 60-person agency and experiencing the decision as devastating. Looking back, she says the crisis exposed an unhealthy business engine and showed that hiding bad news from senior managers had also removed their accountability and participation in solving it.

  • The first large downsizing felt overwhelming and personally heavy
  • Grede believes the change produced a more disciplined company
  • She had kept too much anxiety and information to herself
  • Withholding the full picture weakened shared accountability
  • She later brought senior leaders into problems and possible solutions earlier

I had held so much of the anxiety of what was happening in that company, it not going well to myself.

Emma Grede · 45:00

you need to bring people on the journey and get them involved in what those solves are

Emma Grede · 46:00
#downsizing#accountability#leadership#crisis
Story1:08:30

Why Grede Believes Physical Brand Moments Stick

Grede argues that in-person experiences can create memories that digitally native marketing does not reproduce. She uses a Skims store opening connected to a themed Hollywood diner as an example, noting that her three-year-old remembered the visit and wanted to return days later.

  • Grede sees renewed demand for shared, tangible experiences
  • The Skims activation joined a store with an existing local diner
  • All six days of available slots were booked quickly, according to Grede
  • Her child's later recall served as a personal sign that the moment was memorable
  • She says smaller brands can apply the principle by meeting customers at the point of purchase

in real life experience is always going to be out anything that is like more digitally native

Emma Grede · 1:09:00

getting in front of customers like getting to them and and that physicality of being in front of them

Emma Grede · 1:10:00
#experiential marketing#retail#brand#customers
Story1:20:00

Oprah Gave Grede a Larger Picture of What Was Possible

Grede says environment and exposure set the height a person can imagine. With few visible role models in her immediate world, she watched Oprah and found the example of a thoughtful, articulate Black woman aspirational, even though she did not want the same television career.

  • Grede says people may struggle to imagine what they never see
  • Her early ambitions were often incremental rather than grandiose
  • Oprah expanded her picture of how a successful Black woman could think and move
  • The useful model was a way of being, not a copied career
  • Grede says she leveraged each step into the next opportunity

you can't be what you don't see

Emma Grede · 1:21:30

I've leveraged everything that I've had into the next thing

Emma Grede · 1:22:30
#role models#ambition#representation#oprah
Story1:44:30

Grede's IVF, Pregnancy Loss, and Surrogacy Journey

Grede describes conceiving her first two children easily, then experiencing unexplained infertility, multiple IVF rounds, and three pregnancy losses before having twins through surrogacy. She urges people who want children to discuss and plan for fertility, while her general statements about age, egg freezing, embryo freezing, and fertility windows are personal claims in the interview and should be checked with qualified clinicians.

  • Grede says her fertility experiences differed sharply between her first two and later children
  • She reports pregnancy losses at nine, eleven, and sixteen weeks
  • She describes IVF and loss as isolating and emotionally devastating
  • A surrogate later carried her twins
  • Grede wishes she had spoken more openly with friends who had related experiences
  • Clinical decisions and fertility probabilities require individual medical advice rather than this account alone

I wish I'd have spoken about it more with all of my friends that had gone through it.

Emma Grede · 1:50:30

my twins were born via surrogacy

Emma Grede · 1:49:30
#fertility#ivf#pregnancy loss#surrogacy

Q&A· 1

Q&A1:35:30

Grede on Prejudice Without Internalising Its Limits

Steven Bartlett recounts research he describes as showing stereotype-threat effects when race or gender was made salient before a test, but the episode does not identify the studies. Grede acknowledges that prejudice is real, says she did not experience her identity as a personal limit in Britain, and cautions that race has felt materially different during her years in the United States.

  • Bartlett presents stereotype threat as a research-backed concern but provides no source in the episode
  • Grede says prejudice can be hard to identify directly because people rarely admit it
  • She experienced being distinctive in British fashion offices as an advantage at times
  • She resists internalising another person's prejudice as a limit on her own actions
  • She explicitly says her British experience should not be mapped uncritically onto the United States

It's never something that for me, knowing how I'm hardwired, I would have let get to me in any way, shape, or form.

Emma Grede · 1:38:00

It ain't the same here in America.

Emma Grede · 1:39:30
#prejudice#stereotype threat#race#self-belief

Takeaway· 4

Takeaway36:30

Why Grede Separates Leadership From People-Pleasing

Grede says leaders cannot make every person happy and still avoid all difficult business choices. She describes clear goals and unambiguous communication as her safeguards, while judging hard decisions by whether they fit her values and protect the wider organisation.

  • Grede believes people-pleasing can conflict with leading a focused business
  • She favours explicit goals and straightforward communication
  • She accepts that layoffs and other decisions can leave people disgruntled
  • She says decisions should remain congruent with the leader's values
  • She evaluates a downsizing partly by the jobs it preserves

you can't be a leader and a people pleaser at the same time

Emma Grede · 37:00

I'm somebody that leads with no ambiguity.

Emma Grede · 40:30
#leadership#people-pleasing#communication#layoffs
Takeaway53:00

What an Ambitious Person Needs From a Partner

Grede credits her husband, Jens Grede, with seeing her ability, telling her difficult truths, and reminding her of evidence when she doubts herself. She does not argue that every partner must be a cheerleader, but says a partner who drains self-belief creates a serious problem; mutual interest and respect help a couple grow together.

  • A close partner can identify blind spots and counter self-doubt
  • Support need not look like constant enthusiastic praise
  • Undermining a person's belief in themselves is materially different from being reserved
  • Grede values continuing interest in who each partner is becoming
  • She describes respect and shared growth as central to the relationship

you need somebody that at least supports your belief in yourself so that you can go off and do what you need to do

Emma Grede · 56:00

The secret is just being interested in each other. The secret is just growing together.

Emma Grede · 56:00
#relationships#support#ambition#self-belief
Takeaway1:55:00

Why Grede Created Aspire to Scale Mentorship

Grede says she already spends short morning calls helping founders and wanted a format that could answer similar questions for many more people. She sees a gap in male-dominated business podcasting and intends Aspire to combine her perspective, network, and an honest account of the work behind ambition.

  • Grede says she speaks with a founder for about 30 minutes on many workday mornings
  • The podcast is intended to scale access to those conversations
  • She sees business podcasting as containing many male hosts and a narrower set of viewpoints
  • Several invited guests told her they had not appeared on a podcast before
  • She wants to challenge what she calls toxic positivity around ambition
  • Her stated audience includes people trying to build the life they want

how can I scale mentorship?

Emma Grede · 1:56:30

I just have a very different point of view. I have very different experience.

Emma Grede · 1:57:00
#podcasting#mentorship#representation#aspire
Takeaway2:02:30

Grede Says Feeling Loved Expanded Her Capacity

In the closing exchange, Grede says secure love from her husband, mother, sisters, and children has increased her capacity to learn, give, work, and try new things. She attributes that freedom less to achievement than to knowing that mistakes will not remove the love and safety around her.

  • Grede describes herself as deeply loved by several close relationships
  • She connects emotional safety with greater capacity rather than complacency
  • The security makes large mistakes feel survivable
  • She believes her openness to learning and giving has increased with age
  • She distinguishes this foundation from her professional achievements

I know I feel so safe and so secure and so seen that I can do anything

Emma Grede · 2:04:30

I think that that is because I'm really loved.

Emma Grede · 2:04:30
#love#security#capacity#relationships