Connor Ives on Bootstrapping a Fashion Brand Without Investors or Hype

Connor Ives rejected the incubator model that defined his generation of designers, instead trusting his gut and building the brand entirely independently—a bet that paid off as he went from CSM student to dressing Rihanna at the Met.

Summary of St. Conner Ives. Every timestamp links into the original audio.

The short version

• 00:04:53 — He maintains obsessive attention to health details like fiber intake and flax seeds, a trait he inherited from his health-conscious Midwestern father.
• 00:08:26 — His parents were both self-made professionals—his father a Midwestern therapist, his mother a pediatric dentist who paid through 12 years of medical school herself.
• 00:11:44 — He interned with Wes Gordon at 16, before the designer had major institutional backing, which gave him early exposure to how a young designer operates independently.
• 00:22:53 — Central Saint Martins tried to break him down and rebuild him in their image during the BA program, but he resisted their unconventional aesthetic philosophy and ultimately stayed true to his commercial sportswear vision.
• 00:32:38 — After being rejected from CSM the first time at 19, he doubled down and two years later had a dress worn by Rihanna at the Met Gala, proving his vision rather than conforming to institutional expectations.
• 00:50:24 — His first wholesale season consisted almost entirely of hand-reworked vintage t-shirt dresses, turning a zero-to-half-million-pound operation by doing labor-intensive customization that no production manager initially believed was viable.
• 01:01:56 — He rejected multiple designer incubators and accelerators that approached him, following a gut feeling that external investment would force him to cede creative control at a time when his whole business model depended on doing things differently.
• 01:12:14 — His design philosophy draws from American sportswear tradition and the idea of building a complete world around a brand—living spaces, wardrobes, accessories—rather than the post-war European mentality of staying small and understated.
• 01:17:45 — He plans in six-month to one-year cycles rather than five or ten-year strategies, believing that the moment you get comfortable in a rigid plan is when everything falls apart.

In depth

The CSM pressure cooker: breaking him down to build what, exactly?

Connor Ives describes Central Saint Martins less as an education than an ordeal, one explicitly designed, in his telling, to dismantle a student’s instincts before reconstructing them in the school’s preferred image 00:30:24. The trouble, as he frames it, wasn’t the demolition phase — he says in retrospect he needed to be broken 00:30:17 — it was that he had no interest in what the faculty wanted him rebuilt into. CSM’s dominant aesthetic register, as he characterizes it, ran toward conceptual, materials-driven experimentation (polyfoam, staplers, pyrotechnic runway stunts) rather than the pretty dresses and American sportswear vocabulary he actually loved 00:30:59. He insists this wasn’t a failure of effort; he tried to produce what tutors wanted, and he believes they could sense the insincerity in it even when the technical execution was competent 00:31:26.

That mismatch had real consequences. He was rejected from the BA program outright at nineteen, a blow he says nearly broke him and worried his friends enough that he didn’t leave his room for a week 00:31:55. Rather than reading the rejection as a verdict on his talent, he converted it into resolve: he decided he would make his intentions so unmistakable that doubt would never again be a credible response to his work 00:32:25. Two years later, Adwoa Aboah wore his design to the Met Gala — a vindication he returns to repeatedly as proof that the institutional gatekeeping and his own trajectory were never perfectly aligned 00:32:38.

Even after being admitted, he became a flashpoint inside the school. Once his pieces started appearing on Rihanna and in US Vogue while he was still a first-year student, tutors suspected he no longer wanted to be there, and classmates treated him as benefiting from a shadowy, unearned deal — proto industry-plant suspicion before that vocabulary existed 00:44:44. He stayed anyway, prioritizing the credential and the peer relationships over the external validation he was already receiving, and he reports that tutors eventually came around, admitting privately that they hadn’t understood how he’d pulled it off — but that if they’d offered that generosity earlier, he would have quit 00:46:30. He’s careful not to frame any of this as grievance: he says the adversarial relationship with authority, and with the school specifically, made him a better designer, even if the method was accidental rather than pedagogically intentional 00:46:53.

Bootstrapping a half-million-pound wholesale order with no money and no plan

The origin story of Ives’s label is less a triumphant launch than an improvised scramble that worked largely because he refused to wait until the mechanics were in place. His first wholesale season landed orders from a sales agency and from Net-a-Porter and Matches worth roughly half a million pounds, including a standing order for 2,000 t-shirt dresses 00:50:38 — a number that sounds like infrastructure he didn’t yet have. The product itself was built almost entirely from wholesale vintage t-shirts, sliced down the middle and hand-recomposed into new garments, a process so labor-intensive that the first production manager he approached laughed him out of the room and told him the plan was insane 00:51:15. He only secured production by negotiating full prepayment from buyers, which let him point to cash already sitting in hand as leverage when recruiting someone to actually make the clothes 00:51:29.

This wasn’t efficient or scalable by any conventional operating logic — by his own estimate, 75 to 80 percent of the line sheet in those early seasons was vintage rework, assembled by him plus twelve interns pulled from various London colleges 00:51:41. He’s unusually blunt that the story doesn’t make rational sense on paper, and credits an improvised team of believers rather than any strategic foresight on his part 00:51:51. The implicit admission here is that momentum, not planning, carried the company through its first seasons, and that the aesthetic maturity visible in his later collections wasn’t present yet — he says plainly that he was still figuring it out, and that the early work was not commercial in any meaningful sense, even though outside observers perceived it as instantly successful 00:47:55.

He also pushes back on assumptions about how the money worked, given persistent ’nepo baby’ accusations 00:44:44. He states explicitly that there was no outside investor and no parental bailout — his parents, both self-made professionals, would help if he were in genuine distress but would not have funded a fashion label as a lifestyle choice 00:58:42. What capital existed came from childhood savings, favorable prepayment terms with wholesale buyers, and occasional small loans from friends and clients in exchange for custom pieces — essentially informal bartering rather than structured financing 00:57:21. He also credits his own willingness to walk away from clients who showed signs of becoming bad debts, avoiding the wholesale collapses that hit peers who extended generous net terms 00:56:52.

Saying no to the incubators — a gut call, not a strategy

During the period Ives was building his label, a wave of designer incubators and accelerator-style investment vehicles were actively courting young British talent, and he was approached by at least one, which he declines to name 01:01:12. He turned them down, and he’s candid that the decision wasn’t the product of financial modeling or a worked-out thesis about ownership structures — it was closer to a physical reaction, a recurring sensation he describes as an ulcer in his stomach whenever a deal’s paperwork looked fine on the surface but felt wrong 01:02:02. He generalizes this as a pattern across his career: when something doesn’t sit right, he’s learned to trust the discomfort over the apparent upside.

The reasoning he supplies after the fact centers on autonomy. He says he recognized early that his business model depended on deliberately not following the standard playbook for how a fashion startup is supposed to be run — meaning that ceding control to an external backer would have undermined the entire premise of the company 01:02:44. His stated principle is that if the business was going to take an unconventional risk, it needed to be a risk he owned outright, rather than one engineered by a partner who would reap the benefit without bearing the consequence if it failed 01:02:58.

He doesn’t claim this was obviously the right call at the time — he admits there were stretches, watching peers take incubator money and seemingly accelerate, where he second-guessed himself and felt he’d made a foolish, costly choice 01:03:17. The retrospective vindication only arrived later, as some of those same peers’ businesses became ‘challenged’ or folded outright, a trend he references without naming names but clearly ties to the financing structures he avoided 01:01:35. The company remains, by his account, entirely self-owned, with him as sole shareholder 00:54:42 — a structural fact he treats as inseparable from the brand’s identity rather than as incidental.

Building a world, not a collection: the American sportswear thesis

Ives traces his design philosophy to a specific image: Anna Wintour’s first Vogue cover, pairing a couture top with ordinary Levi’s jeans, which he says functioned as a kind of formative jolt once he understood its significance, not just visually but as an encapsulation of an American lifestyle-brand logic 00:55:30. He explicitly rejects a European, and particularly a post-war British, instinct toward modesty and restraint — the idea of staying small, keeping your head down, and treating overt ambition as distasteful 01:13:57. His stated counter-model is the American lifestyle designer who sells not a single garment but an entire imagined existence: buy the tie today, and in twenty years you’re buying the sport coat, the boots, the bedding, because the brand has built a coherent world around the consumer 01:13:35.

Crucially, he frames his years in London not as a departure from this American sensibility but as the condition that let him understand it properly — distance, he argues, sharpened his reading of the culture he’d grown up inside rather than diluting it 01:14:40. This is a direct extension of his earlier claim that leaving Bedford and attending CSM revealed to him how parochial his inherited worldview had been 00:25:17; here the same displacement becomes the source of design clarity rather than cultural humility.

He pairs this high-concept framing with an openly commercial ambition: the brand, he says, spans ‘high, low, and everything in between,’ deliberately mixing accessible slogan tees and polos with ornate eveningwear, a hybridity he says alienated some observers early on but which he treats as the whole point 01:11:44. He’s unusually explicit that fashion-for-fashion’s-sake experimentation — the kind epitomized by certain long-running, uncompromising arthouse labels — doesn’t interest him, and that commercial success is itself a legitimate creative achievement rather than a dilution of one [2723, by the host’s framing he agrees with]. The unresolved tension he leaves hanging is between that stated commercial instinct and the handmade, unscalable production methods (hand-spliced vintage tees, custom-built relationships with specific wealthy clients) that actually built the brand — a contradiction he never fully reconciles, beyond noting that it worked.

No five-year plan, and a managing director doing the unglamorous work

Asked directly how far ahead he plans, Ives gives an answer he preemptively calls terrible but defends anyway: he doesn’t think in five- or ten-year horizons at all, and treats the mere comfort of a long-range plan as the precise moment a business becomes vulnerable to collapse 01:17:45. He says past consultants brought in to professionalize the operation kept pushing him toward long-term forecasting, and he kept resisting, instead claiming competence only at the six-month-to-one-year scale 01:17:51. The one concrete example he offers — deciding, almost on impulse, to move his runway show from London to New York — came from an emotional data point rather than a market analysis: during a stint back in the US he noticed that new acquaintances and potential clients assumed he was British, which he treated as a warning sign about brand identity slipping from its American roots, and he phoned his managing director the same day to commit to the move 01:18:44.

That anecdote doubles as a tacit admission that his instinct-driven, reactive style of leadership needs institutional ballast to actually function at scale. He’s explicit that the financial turnaround of the company — a shift from a business that merely looked successful to one that was actually profitable — is primarily the achievement of a managing director he appointed relatively recently, someone he says accomplished that correction within about eighteen months 01:19:19. He doesn’t frame this as a contradiction of his gut-driven approach so much as a necessary complement to it: he supplies vision and timing, she supplies structure and financial discipline, and he’s unusually generous in crediting her rather than claiming sole authorship of the brand’s current stability 01:19:37.

What’s left unresolved is how this short-horizon style interacts with the long-range, world-building ambition he describes elsewhere — wanting the brand to eventually furnish bedrooms and country houses, not just wardrobes 01:14:27. He doesn’t attempt to square an avowedly six-month planning cycle with a multi-decade lifestyle-brand vision; he simply holds both claims simultaneously, treating adaptability in the near term as compatible with, rather than opposed to, ambition in the long term.

Summarised automatically. Listen to the original for the full conversation — this is not a substitute for it.