Chloe is from Myanmar. In 2013 she graduated, got a corporate job, and felt completely unfulfilled despite doing everything right. She found fitness that year, started sharing free health and wellness content online for women like her, and people began asking her to coach them. She never intended to build a business. Then COVID hit, and 3,000 to 4,000 people signed up to her first fitness challenge overnight. She called her mum the next morning not knowing what had just happened. The community she has built since — tens of thousands of women, going seven years strong — is what she calls her greatest achievement.
This conversation covers the real timeline, the free work you have to do before anyone pays you, why feeling unfulfilled despite a good job is not a you problem, and what it actually looks like to build something people never want to leave.
Why feeling empty despite having everything is a sign of misalignment, not failure
Was fitness the missing thing or the thing that started everything else
The shadow self and why you expand into new versions rather than kill off old ones
Are entrepreneurs born or made
What Ryan and Chloe were like as students
The 10-year rule Instagram never shows you
What actually surprises you when you start coaching real people
Why women end up doing everything for others and nothing for themselves
What COVID did to two years of quiet building
Building the community you once needed and never had
Why she gave everything away for free first
What men don't understand about women
Managing multiple businesses at once
What she was naive about when she started hiring
Zero fear of failure and why regret scares her more00:43 What actually broke in 2013
04:00 Was fitness the missing thing or just the start
04:59 Were you depressed or just out of alignment
05:46 How do you explain that feeling to someone who doesn't have the words for it
07:54 What part of old Chloe still shows up
09:36 The shadow self and not killing off who you were
10:59 How fitness coaching became a career
12:33 Entrepreneurial DNA: selling stickers in Myanmar at grade five
14:08 Are entrepreneurs born or made
14:53 What were you like at school
17:22 High tolerance for uncertainty and Ryan's bankruptcy story
20:09 Instagram is lying about what entrepreneurship looks like
22:11 Why it actually takes ten years
25:03 What surprised you most about working with real clients
27:17 Why the mindset work is where transformation actually happens
29:12 What coaching thousands of Asian women revealed
31:40 People pleasing, resentment, and looking after others before yourself
33:01 Finding out at 22 or 23 it's okay to say no
34:35 How one hour of fitness gave Chloe ownership of her own life
37:23 What started to break as the business scaled
38:17 COVID and the morning thousands of people signed up overnight
40:36 Why it was never overnight: two years of building came first
41:38 When does life actually start to crack as you scale
44:06 Is the community your greatest achievement
46:07 Are you building the community you once needed for yourself
47:47 Did you start with free or low ticket
50:28 What men don't understand about women
53:14 The pressure on modern men
58:09 When clients come for fitness and stay for everything else
01:01:42 Would you ever work with men
01:03:19 Why expand into activewear in a saturated market
01:05:47 How do you manage multiple businesses at once
01:07:41 What is the highest leverage use of your time
01:11:11 What were you naive about when you first started hiring
01:15:28 Why competition doesn't scare her
01:18:49 Zero fear of failure
01:19:08 What are you building in the next ten years
01:23:56 What does success look like with no money, status, or approval
IG: @dr_ryangleeson
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