Raising money isn't success
Silicon Valley sold us a dream
In today’s issue: The skincare brand selling a product every five seconds, how to make your online shop less boring, and the pitch deck that just raised $3m
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Notes from a messy desk
At a conference last week, they introduced me by saying, “She raised $50 million in venture capital,” and the whole room clapped.
I literally interrupted the audience and said “that’s not the thing to celebrate,” and explained why raising money isn’t an indicator of success.
Building a business that prints cash, that you own, that gives you freedom – that’s success.
I know because I’ve done both.
I bootstrapped my first company to a $60m run rate before venture capital ever entered the picture. I’ve been celebrated as a unicorn founder – and I’ve watched the machine unravel from the inside.
Here’s the truth nobody tells you:
Raising money means you’re on a timer. You’re committing to someone else’s growth targets and someone else’s timeline. It’s not about building sustainably — it’s about building fast enough to justify the bet investors placed on you.
Bootstrapping forces real discipline. You grow based on customer demand, not investor expectations. You focus on profitability, not vanity metrics. And if you eventually sell or stay private, you keep the upside — without needing permission from a board.
The reality is, most businesses shouldn’t raise venture capital.
If you’re building a profitable, sustainable company that serves real customers – especially in industries like services, consumer goods, education, or niche software – you’re better off bootstrapping.
Venture capital is designed for companies chasing massive, global markets – businesses that can realistically 10x or 100x in a few years. Think: frontier tech, AI, biotech, or network-effect platforms.
If that’s not you, you don’t need to play their game.
In my new (free) guide, I’m sharing:
✨ Why bootstrapping builds stronger, more resilient companies
✨ How growing with your own cash – not investor cash – gives you leverage for life
✨ The rare scenarios where raising venture money does make sense – and how to know if you’re the exception
Wheels up,
Sophia
🫖 Tea with GPT — This Week’s Uses
This week I used GPT to…
Find the best time for my mom to fly California → UK — minimizing jet lag (we’re going to Greece)!
Check if a probiotic was still safe — based on a photo and the expiration date.
Compare renting vs. buying in London — financially modeling what makes more sense right now.
Write a script about failure for Instagram DMs — a personal note I could send to 1,000+ followers to build deeper connection.
Learn about T-bills — understanding if it’s a smart move for cash I don’t need short-term.
I asked you what your fringe AI use cases are… what software you can’t live without. And you all delivered. Keep ‘em coming:
Collabs on my radar
The Love List – a style Substack from Jess Graves – just dropped an oversized pink linen shirt with Chava Studio, designer Olivia Villanti’s made-to-measure women’s shirting brand. A need. The New Balance x Miu Miu suede sneakers are a dream, and we’re blessed by the collab gods with a continuation of the partnership – this time, with tennis champ Coco Gauff. It’s good. London-based Rixo is partnering with Dragon Diffusion on a summery, vintage-vibed, seven-piece accessory collection. The Wrangler x Kendra Scott collection is very festival coded. Into this fitted blazer and denim vest for bopping around London parks with the poodles. Madhappy and Crocs just dropped classic clogs with jibbitz made to get sandy at the beach. If I hadn’t just emptied out my closet, I’d look into dropping a few treasures on thrift marketplace Vinted – Alexa Chung just dropped her first pieces on the platform. Fun collab. AriZona (yes, the iced tea brand) and eyewear label Thierry Lasry are partnering on a “futuristic” collection of $99 sunglasses. The brands are hosting a three-day pop-up in SoHo right now to show off the gear and give out tastes of their new hard iced tea (it has vodka). The Chamberlain Coffee cafe added a signature drink to its menu inspired by Dove body wash. Gap and Doen drop their second collection tomorrow.
Collab report: Last week, subscribers were most into the Crown Affair x éliou necklace, the Campbell & Kramer collection for Urban Outfitters, and the ROA x Colin Meredith hybrid hiking sneakers.
Shop my favorite brand collabs.
Links to make you smarter and more interesting
Skincare brand Bubble made more than nine-figure revenues, and its bestselling moisturizer sells every five seconds. Clearly, they’re doing something right. That’s because the brand isn’t just riding the Gen Z wave – they’re shifting gears as its audience matures. In an interview with Vogue Business, founder Shai Esenman broke down how Bubble is evolving with their community. I surfaced the best bits:
Evolve with your audience, don’t outgrow them. Bubble launched Power Wave, a product aimed at older Gen Z and millennials, without abandoning its youthful roots
Turn your marketing into education. Bubble is bringing in expert voices, clinical claims, and ingredient breakdowns to meet a more discerning shopper. Gen Z may want trends, but millennials want results.
Price for loyalty, not just margins. Despite moving toward a more mature product, Bubble keeps prices affordable, proving you don’t need to hike costs to earn trust.
Focus on depth, not breadth. Bubble isn’t chasing new categories — it’s doubling down on skincare, solving specific problems like hormonal acne, and mapping out its future through 2027.
Check out the pitch deck for Series, the AI startup that just pulled in $3.1M to reinvent professional networking. Business Insider has the 11-page pitch deck the company used to raise its pre-seed. The deck leads with the pain point: “the way entrepreneurs connect is broken.”
Rare Beauty has a creator – not a brand – mindset when it comes to Substack strategy. And that’s a good thing. Substack is hot right now, but it’s still early days, especially for brands, which means there’s a lot of opportunity to have fun and experiment on the platform. Which is exactly what Rare Beauty’s director of creative strategy MacKenzie Kassab, who writes the brand’s Substack issues, is doing. She told Modern Retail that they’ve ditched their original content playbook and adjust their strategy daily based on feedback from readers.
The best time to post on Instagram is 3pm on Monday. For LinkedIn, it’s 10am on Tuesday. That’s according to Buffer, who looked at millions of posts across social media platforms to identify the best posting times. Worth brushing up on as you build out your content calendar.
Luggage brand BÉIS went viral for keeping it real about tariffs. CEO Adeela Hussain Jonson told Modern Retail that the brand wanted to “be real with our community.” They got very real – their email includes the word "dumpster fire.”
Vera Bradley is chasing a richer shopper. The company, known for bags priced between $5 and $300, is narrowing its product assortment and redesigning styles to better target younger, more affluent shoppers at a time when customers earning $75k or less are scaling back spending compared to higher-income households who continue to shop.
Only 38% of people would recommend Target after its DEI retreat – an 11-point drop from the previous month. Target had more negative media and social content compared to Alphabet and Amazon, who also scaled back their efforts. That’s because Target had positioned itself as a DEI champion, so the change feels more like a betrayal.
79% of consumers find online shopping lonely, and 78% are overwhelmed with product choices. They want personalization, excitement, a sense of discovery. Your brand’s online presence should…
Curate the experience. Make shoppers feel like the site gets them before they even click.
✨ Glossier tailors product recommendations based on your skin type and purchase history via their Skin Quiz
Charm them with the unexpected. Turn your homepage into a dopamine machine – think delight, not just design.
✨ Charlotte Tilbury spices up the homepage with tarot-inspired product quizzes and “mystery box” drops that turn browsing into a game of chance.
Engage emotionally. Copy isn’t filler, it’s your brand voice holding their hand all the way to checkout.
✨ Reformation is known for its cheeky copywriting, and weaves it into the real-time sustainability stats on each product page (“You saved 15 lbs of carbon!”)
Add exclusivity. If everyone can get it, no one wants it – drop it, tease it, gate it.
✨ Revolve creates buzz with its limited-edition capsule collections that drop with little warning, sparking major FOMO and making you feel like you’re ahead of the curve when you snag one before it’s gone.
Get personal… while respecting privacy. Smart personalization should feel like magic, not surveillance.
✨ Spotify uses your listening habits to create highly personal playlists without feeling too invasive… or at least, the delight outweighs the invasion
Use ChatGPT to value your biz. Researchers are now building AI models to remove some subjectivity from the relative-valuation process. I’ve used ChatGPT to figure out market rates for a brand partnership and even freelance retainers for a project. There’s definitely value in its capacity to help you get a valuation number – it can mine historical data and competing companies in seconds.
London-based illustrator Aysha Tengiz shared a free contract template for artists and creatives to send clients when a project kicks off. “If illustrators understand their rights and together take a stand against bad practice and dodgy contracts, we have a much better chance of surviving this ever-changing creative industry,” she wrote in an It’s Nice That essay on dodgy contracts and copyright.
ChatGPT’s personality has gotten “too sycophant-y and annoying,” according to OpenAI CEO Sam Altman… and a lot of users. Altman said they are working on updates to dial back the ass-kissing.
Link report: Last week, subscribers were most into beige as the new power move, the Boy Smells rebrand backlash, and Kendrick Lamar as the new face of Chanel eyewear.
More from my rich universe of endeavors
I may include affiliate links, which means I receive commission on purchases made from some of the links. But I’ll only show you stuff I really like.
Love this perspective on raising money. Last year i went to a lot of founder/investor meetups and couldn’t shake the intuition that VC was not the direction i wanted for my business, and yet it seems like the thing that legitimizes you in the startup world. Much sexier to succeed without it tbh
💯