June

Coaching a $50M Brand Builder Turned Investor to Attract the Right Founders | Gautam Gupta | Ep 1064

October 2, 2026 by June

“Playing your own game, even though it might not always be a straight line to success, you have only yourself to blame and only yourself to credit.” – Gautam Gupta

Join Niiamah (@niiamahashong) and Gautam Gupta for a live coaching conversation. Gautam’s challenge: making “raise the capital you need” land as more ambition, not less.

You’ll walk away with:

Why refusing to repeat your last mistake is the bigger ambition
Why a better pool beats a better message when you only need a few right people
Why the people meant for your work convince themselves

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

00:41 – $50M Revenue, $1.5M Monthly Burn

03:42 – Every Raise Is a Promise

06:24 – The Founder as Option Bet

12:22 – Do What You Say

16:49 – When Discipline Sounds Unambitious

19:46 – The Blind Ambition Reframe

21:54 – Capital as Fuel, Not Oxygen

28:10 – They Convince Themselves

29:01 – Better Message or Better Pool?

Enter Gautam Gupta’s World:

X | LinkedIn | Website

Continue into Outlier’s Edge World:

Coaching a Fractional CMO to Prove His Framework With Real Results | Marc Ensign | Ep 1063

October 2, 2026 by June

“Nobody’s climbing the other side of this mountain. I wonder what that looks like.” – Marc Ensign

Join Niiamah (@niiamahashong) and Marc Ensign for a live coaching conversation. Marc’s challenge: taking the marketing framework he’s only used for a handful of clients to everyone, with no path yet between idea and fruition.

You’ll walk away with:

Why the path everyone takes is the one nobody notices
How to play like you have nothing to lose, even when you do
Why proof beats population when you’re building something that matters

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

03:12 – Collect 15 No’s a Day

07:17 – Nobody’s Climbing the Other Side

10:42 – I Had Nothing to Lose

18:19 – Everyone Deserves to Be Heard

29:18 – All Trees, No Path Yet

33:32 – The Community Is a Byproduct

38:15 – AI Needs a Direction

43:14 – 100 Winners Beat 10,000 Members

46:46 – Go Find 1,000 Raving Fans

Enter Marc Ensign’s World:

Continue into Outlier’s Edge World:

Coaching an Engineer Turned Pressure Expert to Take Her Method Worldwide | Claire Hayek | Ep 1062

October 1, 2026 by June

“When you name it, you tame it.” – Claire Hayek

Join Niiamah (@niiamahashong) and Claire Hayek for a live coaching conversation. Claire’s challenge: bringing pressure-proof leadership to the whole world while she is still the bottleneck.

You’ll walk away with:

Why pressure is not the enemy, and what beats coping
How to catch yourself rehearsing an attack that hasn’t happened
Why your real bottleneck may be how big you’ll let yourself get

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

02:09 – Forged under pressure in Beirut

09:20 – Pressure is not the enemy

12:02 – You’re allowed: the walking call

19:10 – I’m the bottleneck

26:12 – Has it happened? Not yet.

29:21 – What if it’s easy?

31:43 – What if you’re the pressure?

40:37 – Is she holding herself back?

45:55 – The fear she couldn’t see

Enter Claire Hayek’s World:

Continue into Outlier’s Edge World:

Coaching the Founder of a Bear Crawl Club to Sign Up 3,000 Athletes | Tyler Smith | Ep 1061

October 1, 2026 by June

“We might not agree on everything in life… but we can all bear our own weight and carry it in the right direction.” – Tyler Smith

Join Niiamah (@niiamahashong) and Tyler Smith for a live coaching conversation. Tyler’s challenge: getting thousands of people into a coast-to-coast charity bear crawl when “bear crawl a mile” makes them turn away.

You’ll walk away with:

Why conviction enrolls people when the activity never will
How a middle-difficulty target loses the casual crowd and the hardcore crowd at the same time
The two-tier move: a floor anyone can hit and a stretch for the ones who go hard

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

00:44 – Vanity, Performance, Then Purpose

06:02 – How AI Made It Real

11:02 – The Pledge Behind Everything

20:10 – Koala to Kodiak Badges

25:54 – The Marketing Problem Named

27:17 – Earn Time, Don’t Rush

28:38 – Conviction Sold Me

34:32 – One Minute Beats One Mile

45:33 – Easy Floor, Hard Ceiling

Enter Tyler Smith’s World:

Instagram | YouTube | Website

Continue into Outlier’s Edge World:

Coaching a Neuroscience Coach to Build a Company That Outlasts Her | Suzanne Henwood | Ep 1060

September 30, 2026 by June

“I equip people to love themselves back to wholeness.” – Suzanne Henwood

Join Niiamah (@niiamahashong) and Suzanne Henwood for a live coaching conversation. Suzanne’s challenge: the gap between being a fantastic coach and trainer and running a business.

You’ll walk away with:

Why believing you’re already on the edge keeps you from jumping
How partnership can become the place you hide
Why the ask you make in passing enrolls no one

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

01:06 – Not a traditional coach

04:21 – Zero tolerance standards

08:10 – Acceptance only gets you neutral

10:17 – Radiographer to neuroscience coach

18:26 – Coach versus running a business

20:58 – Thinking you’re on the edge

24:40 – Hiding behind partnerships

25:51 – You’ve already jumped

30:56 – The courageous ask

Enter Suzanne Henwood’s World:

Facebook | Instagram | LinkedIn | YouTube

Continue into Outlier’s Edge World:

Coaching a 25-Year Holistic Chiropractor to Take His Message to Millions | Fred Blum | Ep 1059

September 30, 2026 by June

“Perfect can reach hundreds. Imperfect can reach hundreds of millions.” – Niiamah

Join Niiamah (@niiamahashong) and Fred Blum for a live coaching conversation. Fred’s challenge: he carries a message he believes could change how people live, and he’s been playing small with it.

You’ll walk away with:

Why the tension you feel when you name your vision is the next step, not the problem
How “a little more” and “not too offensive” quietly shrink a powerful message
Why you don’t have to live it perfectly to be the one who carries it

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

05:27 – Pressure works, but costs

21:21 – I’m playing really small

23:17 – The vision creates tension

25:03 – Declare, don’t introduce

27:19 – Five levels too low

31:38 – Too palatable, too small

35:46 – Afraid of being undefended

39:14 – Can’t show up imperfect

43:51 – A leap, not a step

Enter Fred Blum’s World:

Website

Continue into Outlier’s Edge World:

Coaching a Prize-Winning Opera Singer to Turn Past Clients Into Referrals | Susan Heaton-Wright | Ep 1057

September 29, 2026 by June

“Do you yourself believe in what you are doing enough to go and ask them for it?” – Niiamah

Join Niiamah (@niiamahashong) and Susan Heaton-Wright for a live coaching conversation. Susan’s challenge: asking past clients for referrals without feeling pushy.

You’ll walk away with:

Why leaders who once broke the rules for their ambition still hesitate to ask for what their work has earned
How a referral ask becomes a gift to your client, not a favor you take
The “who do you know” question that turns a vague intro into a real handoff

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

01:47 – She stole the application form

03:21 – Underestimating yourself instead

15:09 – “I’m not a vocal coach”

20:02 – Who wins the little box?

22:21 – “I’m English. I can’t ask”

26:29 – Her stroppy 16-year-old self

30:36 – Waiting to be invited

32:34 – The referral is a gift

32:57 – How to audition a referral

Enter Susan Heaton-Wright’s World:

Website

Continue into Outlier’s Edge World:

Coaching a 25-Year Marketing Firm Founder to Plan Her Legacy | Paige Arnof-Fenn | Ep 1058

September 29, 2026 by June

“If you are not a brand, then you’re a commodity, and if you’re a commodity, you’re competing on price.” – Paige Arnof-Fenn

Join Niiamah (@niiamahashong) and Paige Arnof-Fenn for a live coaching conversation. Paige’s challenge: wanting to leave the world better than she found it, and not yet knowing what her part looks like.

You’ll walk away with:

Why leaders who aren’t a brand end up competing on price
What your audience is actually buying, and why it isn’t your product
Why impact that happens by default isn’t the same as impact by design

Timestamps:

00:00 – Welcome to Outlier’s Edge Live

07:48 – What brands really sell

11:39 – Brand or commodity

16:18 – Clarity builds trust

22:13 – Everybody is a brand

25:48 – Choosing a life-changing conversation

27:33 – What’s your flavor of impact?

31:17 – The loss that changed everything

35:35 – Naming her fourth chapter

40:08 – Have you told them?

Enter Paige Arnof-Fenn’s World:

LinkedIn | Website

Continue into Outlier’s Edge World:

June

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