The Diary of a CEODeliveroo Founder: From £0 to £5 Billion: Will Shu | E88
CHAPTERS
- 0:00 – 5:30
Setting the Scene: An Unlikely Founder
Steven Bartlett introduces Deliveroo and frames Will Shu as an anomaly among stereotypical brash founders—humble, understated, and not overtly self‑analytical. They set expectations that the conversation will dig into the harsh realities behind the glossy success story.
- •Deliveroo grew from a lone idea in London to a multi‑billion dollar company.
- •Shu is described as unusually humble and straightforward compared to typical high‑ego founders.
- •The podcast’s aim is to explore the difficult, often hidden parts of building such a company.
- 5:30 – 12:00
From New Haven to London: Early Life and Career
Shu recounts growing up in New Haven, Connecticut, with immigrant professional parents, doing well academically, and taking a Wall Street job more for money and prestige than passion. A transfer opportunity brings him to London, where he quickly decides to stay.
- •Childhood in a modest, frugal immigrant household in New Haven.
- •Parents: mother a scientist at Yale, father an actuary.
- •Top grades lead to a finance role on Wall Street in 2001.
- •Move to London in 2004 on a whim to try something new.
- 12:00 – 20:30
Seed of an Idea: London’s Food Problem and Timing
Working late at Morgan Stanley in Canary Wharf, Shu is appalled that dinner means Tesco microwave meals rather than high‑quality restaurant food in a culinary capital. He first explores the idea in 2008 but realizes it’s too early technically; smartphones and apps haven’t matured yet.
- •Shock at London’s poor late‑night food options compared with New York.
- •First‑day experience in London triggers the Deliveroo concept.
- •Attempted to start Deliveroo in 2008 but blocked by hardware/infra constraints.
- •Business school exposes him to the mobile revolution and offline‑to‑online shift.
- •He decides post‑MBA (2012) to return to London specifically to start Deliveroo.
- 20:30 – 31:00
Finding a Co‑Founder and Building V1
Shu reconnects with childhood friend Greg Orlowski, a former car mechanic turned software developer, to build the first version. Greg codes the restaurant tablet and rider app from the US while Shu in London signs restaurants and riders, launching with a simple website rather than a mobile app.
- •Shu and Greg bonded over early internet and Unix machines as teens.
- •Greg initially doubts feasibility in 2008 due to tech complexity.
- •By 2012 they commit: Greg quits his job, Shu moves back to London.
- •Early build: restaurant tablet, rider app, basic non‑mobile‑optimized website for consumers.
- •Launches Feb 2013 in Chelsea; first months are just the two founders plus a few riders.
- 31:00 – 37:00
Hyperlocal Hustle: Riders, Friends, and Early Traction
The business begins with a handful of riders and 10 restaurants in Chelsea, many recruited through personal relationships. Shu delivers most orders himself, leaning heavily on friends to order for fun before genuine word‑of‑mouth catches on.
- •First area: Fulham Road and King’s Road in Chelsea.
- •Landlord’s restaurant becomes an early partner upstairs from Shu’s flat.
- •Friends order mainly to watch Shu deliver; they keep ordering even when he doesn’t deliver, revealing product–market fit.
- •First ever order: pizza delivered upside down, turned calzone, then eaten by Shu.
- •No paid marketing for first couple of years; guerilla efforts like Shu in a kangaroo costume handing out flyers.
- 37:00 – 42:00
Bias on the Ground: Starbucks and Rider Dignity
Early on, Shu and three Pakistani‑heritage riders used Starbucks as a base while waiting for orders, repeatedly being kicked out by a manager. The dehumanizing way they were treated sears into Shu’s memory and shapes his commitment to rider respect.
- •Riders and Shu camp at Starbucks between orders and are repeatedly moved on.
- •Manager’s demeanor suggests they’re making the shop “look bad,” treating them as less than human.
- •Riders are numb and jaded, indicating such prejudice is routine for them.
- •Shu is angry and recognizes how comparatively privileged he is versus riders from extreme poverty.
- •This episode becomes a formative driver for his focus on rider voice and dignity.
- 42:00 – 48:00
Naming Misfires and the Booze Food Concept
Shu shares early, often terrible naming ideas—“Food Pony,” “Food Mule,” and an initial late‑night drunk‑food proposition called “Booze Food.” This illustrates how messy and unglamorous early branding decisions can be, even for breakout successes.
- •Early name candidates included Food Pony, Food Mule, and Booze Food.
- •Original focus was post‑night‑out food at 3am, inspired by New York’s late‑night scene.
- •A friend suggested a “cheat code” mode for drunk users to surface unhealthy options.
- •Deliveroo branding emerges later, after iterations and abandoning novelty concepts.
- 48:00 – 54:30
Co‑Founder Departure and Distributed Tech Challenges
Greg builds a dev team in Chicago while Shu scales operations in London, but their geographical split becomes a structural problem. Greg’s unwillingness to move to the UK ultimately leads to his exit, leaving Shu without a peer‑level co‑founder inside the company.
- •Greg is critical in building the platform but remains based in the US.
- •He creates an engineering team in Chicago instead of relocating.
- •As Deliveroo gains real momentum, Shu insists on co‑locating the team for a physical–digital product.
- •Greg leaves around late 2015/early 2016; the personal friendship remains strong.
- •Shu reflects that Greg didn’t fully feel the UK‑side momentum and that losing a co‑founder is emotionally difficult and isolating.
- 54:30 – 1:03:00
Entrepreneurship Philosophy: Obsession, Focus, and Avoiding Idea Lists
Shu contrasts his problem‑driven approach with peers who chase financial outcomes, side projects, or status as “entrepreneurs.” Both he and Bartlett argue that without genuine care for the problem, founders will quit when chaos hits.
- •Shu is not chasing entrepreneurship as an identity; he’s solving a food problem he cares about.
- •He criticizes friends who maintain lists of abstract ideas based solely on potential financial upside.
- •He opposes juggling multiple side businesses; believes you must pick one and be all-in.
- •They discuss Steve Jobs’ view that only irrationally committed people survive the chaos.
- •Bartlett echoes that building for money or status alone usually fails under pressure.
- 1:03:00 – 1:09:00
Embarrassment, Identity, and Delivering to Ex-Colleagues
Shu recounts delivering pizza to a former hedge‑fund colleague who assumes his life has gone off the rails. He also describes friends questioning why he’s “just delivering food” after prestigious finance roles, and how he chooses to ignore perceptions and focus on building.
- •A former colleague, Gianluca, opens the door shocked and asks, “Is everything okay?”
- •Friends see Shu delivering five hours a night and worry he’s wasting his elite career.
- •Shu insists he never considered quitting, unlike Greg; he felt responsible to stakeholders.
- •He views not caring what others think as a personal trait and, arguably, a founder superpower.
- •Bartlett links this to his own experiences of class and racial prejudice in “first class” spaces.
- 1:09:00 – 1:15:00
Scaling Up: Hiring on Gumtree and the 20–100 Employee Sweet Spot
With some early traction, Deliveroo raises an initial £2.7m round from Index Ventures and starts to scale. Shu learns hiring by trial and error via Gumtree and reminisces about the scrappy illegal office and his favorite company stage: 20–100 people.
- •First institutional round: £2.7m from Index felt huge at the time.
- •Shu, with only finance experience, posts job ads on Gumtree to build the early team.
- •The first “office” is an illegal, windowless room with scavenged furniture, costing £1,000/month.
- •He finds years 2–4 the most fun: fast growth, everyone aligned, informal communication.
- •He candidly admits being CEO of a large public company is less fun than those early days.
- 1:15:00 – 1:18:00
Mental Health, Anxiety, and Founder Flat Affect
Asked about mental health, Shu describes himself as emotionally steady rather than volatile but admits to prolonged periods of extreme pressure, especially when facing existential issues. He references Elon Musk’s “chewing glass, staring into the abyss” description and says it resonates.
- •Shu doesn’t see himself as highly up‑and‑down; worries this might mean he suppresses things.
- •Early on he was prone to “going nuts” over bad order handling or customer service, but has mellowed.
- •He acknowledges many “chewing glass” periods that lasted far longer than hours or days.
- •He suggests many parts of the journey are “super, super, super hard,” not just glamorous high points.
- •Bartlett probes whether, knowing this, Shu would still have started; Shu says it depends on eventual outcomes.
- 1:18:00 – 1:26:00
Funding Shock: Losing the SoftBank-Like Round and Recovering
In 2017 Deliveroo is days away from closing a roughly $600–700m investment from the world’s biggest fund when the deal collapses, reportedly due to that investor’s entanglements elsewhere. Shu must rapidly re‑fund the company or face running out of cash.
- •Term sheet signed and diligence underway for a very large round (~$600–700m).
- •Three days before close, the investor pulls out, citing external reasons (linked to Uber).
- •Shu is furious for about 10 minutes, then immediately mobilizes the team.
- •They line up ~25 investor meetings globally and raise from firms like Fidelity and T. Rowe Price.
- •Illustrates how fragile even late‑stage deals can be and the need for fast, decisive recovery.
- 1:26:00 – 1:42:00
The Amazon Investment, CMA Battle, and COVID Double Hit
Amazon agrees to invest as a minority shareholder, but UK competition authorities freeze the funding while conducting an unprecedented phase‑1 and phase‑2 review over ~16–18 months. Simultaneously, COVID causes partner restaurants to shut both dine‑in and delivery, cratering orders and forcing major layoffs.
- •Amazon takes ~13–14% as a minority investor with one board seat; capital is blocked by CMA.
- •CMA runs phase‑1 and then phase‑2 investigation, leaving Deliveroo in limbo for over a year.
- •Deliveroo must keep competing against well‑funded giants without access to the new capital.
- •COVID hits; many restaurants shut entirely, not just dine‑in, leading to disappearing inventory and users.
- •Shu executes large layoffs during maximum uncertainty, calling it the hardest thing he’s ever done.
- •He contrasts solvable business problems with the powerless feeling of waiting on a government body.
- 1:42:00 – 1:54:00
Founder Loneliness, Relationships, and Life Imbalance
The conversation turns to the toll on Shu’s personal life: he admits being obsessive, having limited capacity for romantic relationships and friendships, and rarely reflecting on his past. Bartlett wonders aloud if they’ve mis‑prioritized life by chasing success so singularly.
- •Shu describes himself as highly obsessive with limited “brain space” for other commitments.
- •He rates his friendship maintenance performance “five out of ten” and calls the job solitary.
- •They discuss the difficulty of compromising on time in romantic relationships as a founder.
- •Bartlett shares his own worry that he may regret under‑investing in relationships long term.
- •Shu says he rarely looks back or questions his priorities, but acknowledges he might be “hiding” from something.
- 1:54:00 – 2:02:00
Going Public: IPO Highs, Market Backlash, and Media Scrutiny
Deliveroo’s IPO is a milestone but the stock’s initial drop triggers intense media criticism and internal concern. Shu says he usually doesn’t care about public opinion, but the ubiquity of the coverage made the first weeks post‑IPO emotionally tough.
- •The IPO validates a journey from idea to major public company with a large market cap.
- •Day‑one trading is weak; media brands it a ‘flop,’ saturating news coverage.
- •Employees and investors bombard Shu with questions as sentiment turns negative.
- •He insists he now focuses on building the business, not daily share price fluctuations.
- •He remains optimistic that years of product and strategy work will pay off over time.
- 2:02:00 – 2:10:00
Riders, Classification Debate, and Will’s Night in Notting Hill
In the context of public debate over whether riders are employees or contractors, Shu emphasizes his direct experience doing deliveries, including a fresh shift the previous night. He describes rudeness from a restaurant and how such field observations feed back into operational changes.
- •Shu still rides; he did five deliveries in Notting Hill the night before the interview.
- •He uses these shifts to test the rider app, get exercise, and get unfiltered feedback.
- •He experiences dismissive treatment from restaurant staff and notes how often riders endure this.
- •He documents such incidents and follows up with restaurants to push for better processes and respect.
- •He asserts Deliveroo’s current model is best for riders but acknowledges there is room to improve.
- 2:10:00 – 2:18:00
Competition and the Emotional Future of Food Delivery
With giants like Uber and Just Eat as rivals, Shu frames online food as an enormous, under‑penetrated market. He argues that the winner will be the company that turns apps from transactional ordering tools into emotional, content‑rich food experiences.
- •Online food is 3–5% penetrated in Deliveroo’s markets versus ~50% in travel.
- •Food is perishable and emotional, making it harder to digitize than other retail categories.
- •Today’s apps, including Deliveroo’s, are “pretty transactional,” focused on utility.
- •Future vision includes restaurant storytelling, content from grocers/FMCG, recipe kits, dine‑in, and possibly private chefs.
- •Goal: users open Deliveroo to learn about food and feel a connection, not just to satiate hunger.
- 2:18:00
Money, Meaning, and Separating Will from Deliveroo
In closing, Bartlett probes Shu’s relationship to money and his long‑term aspirations. Shu says his lifestyle hasn’t changed much, he doesn’t think about wealth often, and he’s more interested in understanding how much of his life’s trajectory is self‑chosen versus being pulled along by the company’s gravitational force.
- •Shu says he lives similarly to 7–8 years ago and doesn’t buy much.
- •He concedes more money is better than less but doesn’t tie it to major happiness gains.
- •He’s curious whether he’s been consciously steering his life or mostly riding Deliveroo’s momentum.
- •He wants to better understand where his own ambitions diverge from or align with the company’s journey.
- •They discuss the need for founders to create space—holidays, therapy, reflection—to disentangle identity from the business.
- •Bartlett invites Shu back once he’s had time to explore that separation and new life dimensions.
