Midnight Breakfast Podcast

Just before he left for Japan for Polofest, I had the privilege of sitting down with Jake Woolf - one of Substack’s top voices on fashion and style - to talk about how he built his creator business after over a decade in fashion journalism at some of the industry’s biggest names.

Episode description

Menswear journalist and creator Jake Woolf went from Hypebeast and GQ to building a Substack and TikTok business on his own. He tells Dan why freelancing for publications stopped adding up, what chasing virality did to his work, and why he now wants fewer wide-net videos and more deep dives on small, American-made brands. They also get into what makes a brand partnership feel real, why brands confuse popularity with influence, his plan to start making long-form YouTube videos, and his midnight breakfast order.

Key points

* Freelancing alone rarely pays. Jake calls supporting yourself freelancing for publications in your 30s “nearly impossible” and says that was his push to build his own audience.

* Substack needed a bigger top of funnel. With about 10,000 Instagram followers, he started making TikTok videos to drive signups, and the videos became roughly half his business.

* Growth for its own sake wore him down. At the peak he added about 1,000 followers a day, then stressed over any video under 100,000 views. He now makes what he finds interesting and treats reach as a bonus.

* Early videos were deliberately basic. Explainers like “what is selvedge denim” felt entry-level to him but built the audience that lets him go deeper now.

* Creator block has a fix: go deeper, not wider. One topic like denim can fuel dozens of videos if you pick a specific mill, pair or detail.

* Best partnerships feel authentic. His Ralph Lauren work, including a trip to the Milan show, worked because he loves the brand. Brands now give creators room, and he builds the product into a video he would have made anyway.

* Product collabs with small brands are about passion. Brands like Manresa and Mark the Tailor can’t pay for a video, so they co-develop products made in the USA instead.

* Popularity is not influence. A creator’s video can perform well and still not get anyone into the store. Brands should pick people whose audience actually cares about the product.

* The influencer 1.0 playbook doesn’t interest him. He’d rather tell stories about small brands, mills and makers than “get ready with me” content.

* YouTube is next. Reels cap him around three minutes, so he wants 25 to 30 minute videos, plus a business model that depends less on brand deals.

* His advice to new creators: keep going, keep trying different things, and remember that a post no one sees costs nothing.

Timestamps

Topic

00:00

Intro and welcome

00:40

Origin story: Hypebeast, Complex’s Four Pins, GQ, then Substack

03:33

Being on social before it was a business

07:08

Getting over “cringe mountain” on camera

10:01

The inciting incident: why freelancing wasn’t enough

13:08

Blowing up on TikTok and the growth trap

15:17

What a typical day looks like

20:31

Creator’s block, and going deeper on topics

22:33

Is he an entrepreneur? The business behind a one-person brand

23:58

Proudest partnership: Ralph Lauren

25:50

Influencer partnerships vs. product collaborations

29:22

What makes a brand partnership work

33:19

When a brand deal is the wrong fit

35:01

State of menswear and menswear influencers

41:25

How brands can go to market better

42:34

Popularity vs. influence

47:04

Advice for aspiring creators

49:10

What’s next: YouTube and long-form

52:12

Dream collab for 2027

53:23

Where to follow Jake

54:00

The Midnight Breakfast question

Quotes and mentions

“I do think sometimes brands mistake like, popularity for influence.” (42:34)

“I think it’s like the most important American men’s fashion brand of all time. Like it is the holy grail to me.” (23:58)

“If you keep trying, you might make it, and if you stop trying, you definitely won’t.” Jake, quoting Seth Rogen (47:27)

Brands and people mentioned: Hypebeast, Complex (Four Pins), GQ, Ralph Lauren, Movado (Heritage Kingmatic), Manresa, Mark the Tailor, Million Goods (Fort Greene), Gap, Audi, Wendy’s.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit midnightbreakfast.substack.com

In this episode of Midnight Breakfast, host Dan Feldstein sits down with Stefano Marrone, CMO of Siebert Financial, for a wide-ranging conversation about the realities of modern marketing leadership. Stefano shares his unconventional path from Milan's creative agencies to founding his own shop in London, through a successful earn-out, and into the fractional consulting world that eventually led him to a full-time CMO role at a publicly traded financial firm.

The discussion covers the daily balancing act of a CMO — translating creative vision into Excel-sheet language for the C-suite — and the surprising reactivity of an in-house role versus agency life. Stefano pulls back the curtain on marketing in a regulated industry, from SEC filing windows that can upend media buying plans to the Kafkaesque realities of compliance reviews. He offers a sharp take on the post-COVID and AI landscape, arguing that as AI makes production value cheap and falsifiable, what's left that matters is craft, taste, and in-person experience.

The conversation digs deep into reaching wealthy audiences — the paradoxes of targeting people who pay to not be advertised to, regulatory barriers to income-based profiling, and why a golf tournament might still beat a digital experiment. Stefano explains Siebert's challenger brand strategy through the lens of their founder Muriel Siebert's story (the first woman on Wall Street), and how the firm finds success in underserved niches: collegiate athletes, military veterans, and women in media.

The episode closes with Stefano's practical playbook for selling content initiatives to a skeptical C-suite (cook with what you have, find an internal champion, start shoestring), his thoughts on marketing education's broken bridge to the profession, and why nonlinear careers and side hustles should be celebrated rather than screened out by AI-powered HR tools.

Show Notes

Guest: Stefano Marrone, CMO of Siebert Financial Host: Dan Feldstein

Chapters

0:00 Welcome to Midnight Breakfast — Dan introduces the show and guest

3:42 Being a CMO Today — The balancing act between strategic thinking and hands-on execution; translating creative into C-suite language

6:24 From Agency to In-House — How the CMO role looks different from the brand side; the surprising reactivity of in-house marketing; the soccer team dynamic of credit and blame

12:01 Marketing & Compliance — SEC filing windows, quiet periods, and the Kafkaesque realities of compliance in financial marketing

13:45 AI & the Post-COVID Shift — Why experiential is back with a vengeance; how AI makes production value cheap and falsifiable; the "nuggets of reality" thesis; Gen W vs. Gen Z audience divides on authenticity

20:16 Reaching Wealthy Audiences — The paradox of targeting people who pay to not be advertised to; regulatory barriers to income-based profiling; why events and experiences beat digital for luxury audiences

25:55 Challenger Brand Strategy — The Muriel Siebert founder story; riches in niches; serving collegiate athletes, military veterans, and underrepresented wealth segments

31:47 Content & Community Building — Why content is Siebert's strongest pillar; the veteran entrepreneur show with 1.5M monthly listeners; "make the logo smaller" philosophy; newsletters as the trust signal AI can't fake

36:08 Selling Content to the C-Suite — The shoestring playbook: find an internal champion, start small, prove results, then ask for budget; why thought leaders outside marketing are the key to content success

47:59 Marketing Careers & Education — The distinction between creators and marketers; the broken bridge between university and industry; why nonlinear careers and side hustles should be hired, not screened out

63:16 Looking Ahead — Optimism about coding no longer being a barrier; the midnight breakfast order: steak and eggs

64:49 Where to Find Stefano — LinkedIn (Stefano Marrone), Instagram (@sdumefy for illustration work)

Key Takeaways

The CMO as translator: The core of the role is translating creative and marketing strategy into language the C-suite — "somebody that mainly reads Excel sheets every day" — can understand.

AI flips the value equation: When production value is cheap and falsifiable, craft, taste, and in-person experience become the new signals of brand investment.

Wealthy audiences require old-school tactics: Digital targeting is broken for luxury — regulations prevent income-based profiling, and wealthy consumers pay to remove ads. Events and experiences outperform.

Content strategy starts shoestring: Don't ask for budget upfront. Find an internal champion, build a minimal season, prove results, then scale.

Hire the nonlinear: AI-powered HR screening filters out transferable skills — exactly the people marketing teams need most.

Mentioned in the Episode

Siebert Financial — siebert.com

Muriel Siebert — first woman to hold a seat on the NYSE

Cash Larsen — host of Siebert's military veteran show

Unit Nine — Stefano's former agency (acquired)

Leo Burnett, Ferrero, Campari, Ethereum — brands/campaigns referenced

Umberto Eco — on giving a megaphone to "the idiot of the village"

Glengarry Glen Ross — "always be selling" (subverted)

Zaha Hadid — where Stefano's best hire came from

Find Stefano

LinkedIn: Stefano Marrone

Instagram: @sdumefy — illustration and sketching

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit midnightbreakfast.substack.com

Midnight Breakfast host Dan Feldstein talks to content creator Rachel Tyers, also known as rachel.points, about her path to becoming a full-time creator, brand partnerships, the best travel experiences and points partners, and more.

00:00 Episode #1: Pointsmaxxing with Rachel Tyers aka rachel.points

00:34 Origin Story

10:55 Overcoming the Cringe Phase

12:48 Building the Business

24:49 The First 100 Posts

28:13 Brand Deals & Partnerships

36:49 Best Points Programs

38:16 Best Airlines & Hotels

44:08 Dream Destinations

47:06 Creators She Admires

50:17 What's Next

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit midnightbreakfast.substack.com

Dan Feldstein, marketer and entrepreneur, introduces his podcast Midnight Breakfast - a source for conversations with marketers, media executives, creators, and founders about what's next.

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit midnightbreakfast.substack.com