I invest in killers building painkillers
I feel really bad for Docusign
In today’s issue: How Plot read beauty shoppers’ minds, Reddit’s brand goldmine, and how ChatGPT helped a Vogue writer discover a new brand
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Notes from a messy desk
One day, I got a notification through the Slack channel I have set up to pull in cold pitches from Trust Fund’s website. I clicked, I read the deck, and I immediately emailed the founders.
That startup was Agree.com, and earlier this week they announced a $7.2M seed round led by Pelion Ventures, with participation from Hustle Fund, Better Tomorrow Ventures, Everywhere Ventures, 8-Bit Capital, and others (including me!). Shockingly, they had so much investor interest they had to turn down one of the biggest podcasters and internet personalities in the world who was alerted to the deal just a little too late (my intro, but it moved too fast!).
Agree is rethinking contracts from the ground up. Not just digitizing signatures, but rebuilding the entire experience of creating, collaborating on, and getting paid through contracts. I invested in the pre-seed round not just because I believed in the product, but because I selfishly needed it. And I’ve been using it ever since.
Watching them grow from a raw idea into a beautifully executed product used by over 25,000 people in under a year has been incredible. But the more interesting story is what they’re quietly replacing — and why.
DocuSign is a dinosaur. It was built for attorneys billing by the hour. It’s rigid, transactional, and completely divorced from what most modern businesses actually need. You sign a document, get a notification, and then have to send an invoice, track it down, nudge the client, follow up again, and maybe (hopefully) get paid.
Agree is what comes next. Here’s how it works:
You upload a PDF, and it becomes instantly editable and collaborative, like Notion for contracts.
You send it — it gets signed in a clean, intuitive flow.
The contract becomes the invoice. Stripe integration kicks in and payment happens instantly.
It’s a no-brainer for freelancers and consultants who want to look buttoned-up without chasing invoices. For creative agencies managing multiple clients, scopes, and revisions. For coaches, service providers, and boutique studios who need structure without the bloat. For SaaS founders and early-stage operators who want legal infrastructure that feels like 2025, not 1984.
And for anyone else sick of juggling DocuSign, Stripe, QuickBooks, Gmail, and their own memory.
Agree also brings real version control — not the “Final_v2_(ACTUAL_FINAL).pdf” kind. Every change is tracked. Every edit is attributed. You can see who changed what, when, and roll back if needed. In short, I feel really bad for DocuSign.
The team is lean, fast, and has taste. Will Hubbard and Marty Ringlein aren’t just building a product — they’re building an inevitable shift in how we do business. I like to say that at Trust Fund I invest in killers building painkillers, and they’re doing just that.
Check ‘em out here.
Wheels up,
Sophia
🫖 Tea with GPT — This Week’s Uses
This week I used GPT to…
Figure out how to remotely renew a street parking permit for my tenants in LA
Get the verdict on whether Apple or Google Maps is best for Lime bike routes across London
Scan an uploaded contract to figure out who to invoice for a recently completed partnership
Scan another agreement to extract the VIN of my 2023 Land Rover Defender that’s for sale (it’s in LA, HMU if you’re in the market!)
Evaluate the quality of my broadband by uploading a screenshot of my speedtest.net results
Choose which Greek Island to whisk my mom away to for her birthday in September
Consult on existential topics like motivation, meaning, and how to make the most of my time on earth
Collabs on my radar
One of the more talked about collabs – Gap and DǑEN’s latest collection. Into the pointelle cardigan. Also into the Aureum x Parke collection. Look at this Italian leather belt and wide leg jeans. Designer pimple patches are here thanks to the Marc Jacobs collab with Starface. Of course they’re already sold out. You can now pre-order the RIXO x Dragon Diffusion collection of woven bags and belts. Olive & June teamed up with Gen Z skincare brand Bubble on a line of mini polishes with limited-edition colors. If I was romping around a riverbed I would want to do it in these algae green KEEN x Hiking Patrol sandals. The Dr. Squatch soap with Liquid Death is incredible – Grime Reaper is made with Liquid Death mountain water, sea salt, and agave extract. And the branding is killer. Australian gelato chain Gelato Messina created a beetroot and dark chocolate flavor for Loewe’s new flagship store in Sydney. They doled out free scoops – inspired by the fashion house’s home fragrances – for two days earlier this month. & Other Stories and ROKSANDA are dropping a limited-edition collab next week. It looks gorgeous.
Collab report: Last week, subscribers were most into the New Balance x Miu Miu sneakers, the Love List x Chava pink linen shirt, and the Wrangler x Kendra Scott collection.
Shop my favorite brand collabs.
Links to make you smarter and more interesting
Only 28 out of 54,000+ Sephora Sale comments on social media mentioned tariffs. Plot founder Megan Duong (seen above!) used her own social listening platform to analyze thousands of comments on Instagram and TikTok posts about the sale to determine that beauty shoppers care more about deals, hauls, and restocks than tariffs and policy discourse. This is also a genius way to market your product – using this trending moment to subtly show off Plot’s superpowers for marketers.
A must-bookmark for anyone running paid ads on Facebook. This updated guide from Buffer lays out all the current Facebook ad sizes, formats, and file types in one place so you can actually focus on creative, not combing through Meta’s help docs.
A 26-year-old Vogue Business writer asked ChatGPT for a white button-down to take her from the office to after-work drinks. The result was a mix of hits and misses, but one standout gem: a $148 shirt from Almina Concept, a brand she’d never heard of. It wasn’t flawless, but it showed AI’s potential to make shopping feel like advice from a friend that’s kind of tapped in. If you’re not connecting with your potential customers on a deeper level, you’re missing out. The future of shopping is about context, authenticity, and making your brand feel like a trusted advisor.
Walmart’s cranking out trend-driven fashion in as little as six weeks thanks to a new generative AI tool that can scan red carpet events. The retailer’s new AI tool, Trend-to-Product, isn’t just spotting trends – it’s generating mood boards, slashing design timelines, and compressing the entire product development cycle. What’s smart here is how Walmart is integrating generative AI with its internal data – training it on its own brand DNA rather than just chasing whatever’s viral.
Your brand’s probably not eavesdropping or engaging on Reddit – but it should be. 93% of brands aren’t using the platform, but those who are are seeing real results. Dove tapped into Crumbl cookie fandom on Reddit by mimicking how users leak flavor drops, and it worked: their collab announcement drove more daily impressions than any of their past campaigns. Reddit’s ad revenue is now growing faster YoY than other social platforms, and 40% of posts mention brands – whether those brands are active or not.
You didn’t build your business to get bogged down in the boring stuff. AI is the shortcut. If you’re completely new to the generative AI space, get the 101 in this new Wall Street Journal guide. Then dive into some of these creative chatbot gems:
Nail your product descriptions in half the time. If you’re great at making, not writing, let AI handle the rest. Feed AI your product features, and it’ll spin up a product description in seconds. Then, tweak it to your voice. More time for design, less time fighting with copy.
Generate viral marketing ideas. Running a campaign doesn’t have to be a months-long slog. ChatGPT can brainstorm 30 viral TikTok ideas for your new product launch based on trending themes, hashtags, and your niche.
Research your competitor’s next move. Ask ChatGPT to summarize the latest moves by your competitors, from new launches to social media campaigns, so you can adjust your strategy on the fly.
Write personalized client pitches at scale. Use AI to create tailored client pitches that are hyper-relevant to each lead – based on their business model, goals, and pain points.
Draft pitches for the press. Tell AI about your latest product, initiative, or story, and let it craft a PR pitch that’s compelling and, most importantly… short and sweet.
Build custom surveys for your audience and customers. Input your key business questions and let AI generate customized surveys – whether it’s for a product launch or brand loyalty check.
It’s a sharp moment for brands to push their hybrid products. Consumers are leaning into versatility – buying fewer things that do more. This Business Insider piece breaks it down. You don’t need a full product pivot, just a creative lens. Look to your community: how are people using what you’ve already built in ways you didn’t expect? That’s your marketing angle.
Shira Lazar, who has worked as a creator for two decades, is building a therapy service for creators. CreatorCare will offer therapy and mental health services designed for creators on a sliding-scale access, with sessions costing as low as $60, whether or not you have health insurance.
Small businesses in the U.S. are losing $153 billion a year to hidden fees – $7,200 per business just on international payments. There are a few approachable things you can start doing right now to avoid sneaky costs, which Entrepreneur outlines here. This one’s key, if you’re not already doing it: Set up transaction alerts so you're not blindsided by surprise charges. If you’re not checking your statements regularly, you’re leaving money on the table.
Link report: Last week, subscribers were most into my bootstrap guide, the pitch deck for Series, the best time to post on Instagram, and Rare Beauty’s Substack strategy.
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.
Sophia, the best bike map route for London is actually CityMapper! It gives you three routes - fastest, normal, and quiet for those of us who want the chillest route. Also, good point on Reddit: used to lurk on there plenty when I worked at Glossier.
“Consult on existential topics like motivation, meaning, and how to make the most of my time on earth” on man, this resonated with me. I have saved thousands on therapy but I do pity my chat gpt having to deal with all of my inane contemplations 😂😂