Mark my words, VYS // IRL is going to be the biggest thing for tech nerds since iOS 7 eliminated skeuomorphism in Apple's design system.

Join hosts Arjun Dev Arora and me (Gregory Kennedy) for the second invite-only VYS gathering in San Francisco of AI-first founders and forward-thinking VCs reshaping the future of software. ​

Fireside chats with:

For Q1 of 2026, we have secured the AWS Builder Loft in SF for our event on Wednesday, March 11, 2026. If you’re a founder or investor, apply here to attend.

I still have a few sponsorship opportunities. Reply to this email if interested.

Founders: Aditya Rohit and Chilarai Mushahary
Location: San Francisco Bay Area
Stage: Pre-Seed
Website: Swytchcode.com
Social: LinkedIn

Confusing docs, slow support, too many languages, and brittle integrations can kill API adoption. SwytchCode treats APIs like a product experience problem, not a documentation problem, by acting as a 24x7 AI solutions engineer for your API.

SwytchCode sits between the API publishers and developers. It lets developers generate production-ready integration code with in single click across 15+ languages. Which makes API integration easier instead of adversarial.

Most companies keep throwing resources at the problem. Hiring support and writing more docs to help devs navigate API integration. SwytchCode attacks the root cause and gives developers working code fast, not better manuals.

This list is built for shipping, not chilling. High energy, no filler, no safe picks. Dark pop, club grit, trap edges, and confidence on repeat. Blast it late at night, on loudspeakers. If it does not make you want to move faster, cut deeper, or push one more ChatGPT prompt, it does not belong here.

Paul and I were lucky enough to have had Court Lorenzini on the Gregory and Paul Show a few weeks ago for a really interesting and in-depth conversation where we covered startups, entrepreneurship, and, of course, grit.

Court grew up in Silicon Valley in the early days, around the pioneers of Silicon Valley that people like me have only read about. His father was an inventor and early venture capitalist, and Court was literally part of the Fairchild crowd as a family friend. This had a big impact on shaping how he thinks.

Court went on to co-found and lead DocuSign starting in 2003, turning e-signature into a default workflow for business. He is also an active investor across dozens of companies and 19 VC funds, and he now runs Founder Nexus, an invitation-only community designed to help venture-scale founders learn from other founders with lived experience.

It was a true masterclass on what actually makes startups work. Not theory. Not another framework or playbook.

Here are six lessons that stuck with me.

Court did not start DocuSign because he woke up with a grand vision for contracts. In 2003, a former employee, Tom Gonser, brought him a set of leftover assets from a failed company his board wanted to sell off. Court took a look and noticed two things worth building around. A clear name, DocuSign, and an issued patent for signing over the internet.

That was enough. They acquired the assets, spun them out, and started building. The lesson is that most founders wait for inspiration when they should be looking for something usable. A small edge. A real customer pain. A defensible angle. You can start from that and earn the bigger story later.

DocuSign’s break in distribution did not come from ads or brand campaigns. It came from a deal with the National Association of Realtors, whose software is used across the real estate industry to generate the paperwork for buying and selling homes.

Court negotiated an embedded licensing arrangement, so DocuSign became a simple button inside that workflow. That put it in front of millions of realtors and home buyers without asking anyone to learn a new tool or process. He also insisted the signature stamp itself say “DocuSigned,” so every completed contract woud promote the product. The result was a massive compounding distribution, because the same people who used it to buy a home would bring it back to their jobs and ask, “Why are they still printing and signing and faxing contracts?”

Their product was an easy sell to business teams. They were able to move faster and with less friction. The blocker was legal. Federal law e-signature law existed, but there was little courtroom precedent, so chief legal officers would not risk core contracts on something untested.

Court’s was able to manufacture the missing proof. He hired a judge, jury, and attorneys to hold a mock trial retry a fraud case as if it had been signed in DocuSign. He then used the judge’s written opinion, which argued the digital trail was stronger than ink, to unlock enterprise approvals.

A lot of the advice he received was sincere, well-structured, well-intentioned, and also dead wrong. The worst guidance tended to come from investors and board members who had never been founders themselves. They had observed startups, funded startups, and even managed large organizations, but they had not carried the burden of making hard decisions as a founder.

By contrast, the most valuable guidance came from other venture-backed founders. People who had already made the ugly calls, hired too early, hired too late, overbuilt, undersold, misread the market, then figured out what actually mattered. They could tell him not what sounded good, but what worked for them under pressure. This was his motivation to start Founder Nexus. His goal is to get founders in the room with other founders, share lived experience to help precent others founders from making the same mistakes and learning every lesson the hard way.

The best founders treat the market like a signal system, not a judge. Every sales cycle, onboarding call, objection, and reason for churn is information about what is actually true. Not what you hoped was true.

The mistake many make is believing conviction means sticking rigidly to the plan. But adaptability and a willingness are much more important. For example, you think you are selling to an enterprise, but the only buyers moving quickly are mid-market. Or you think the product is the blocker, but the real blocker is legal, security, or procurement. Or you think you need more leads, but the real issue is that the buyer cannot justify the risk internally.

The founders who win do not argue with those signals. They change how they position the product, package it, distribute it, and earn trust, until the path to yes becomes obvious. Stubbornness is insisting that the market is wrong. Adaptability is accepting feedback and changing the approach quickly enough that the market never gets a second chance to ignore you.

Early on, DocuSign could be used almost anywhere. Sales contracts, HR forms, NDAs, or loan documents. That flexibility was tempting and dangerous. What actually worked was leaning hard into one use case that pulled the company forward on its own. Real estate. The Realtor workflow produced real revenue, real volume, and real proof, and it stayed the largest driver for years.

The lesson is that product market fit is not theoretical breadth. It is one concrete use case that works so well that it funds everything else. Once you own that, expansion becomes a choice instead of a hope.

I think what makes Court’s story so inspiring is how he overcame obstacles when there was no obvious path forward. At each inflection point, he identified the constraint and addressed it effectively.

If there is a meta lesson here, it is this. Progress comes from reframing problems and seeking smart solutions, not from pushing harder on the first solution.

🎙️ 031 Gregory and Paul Show - Will Vibe Coding Make Software Free?

On this episode, Gregory checks in from San Francisco with a field report from Llama Lounge, an AI meetup that’s become a real-time barometer for startup hype. From there, the conversation moves into where founders are still finding opportunity in AI, why hardware and industrial workflows are back in focus, and why vibe coding is now the default assumption, not a novelty. The back half of the show hits token economics, agentic commerce, ads inside LLMs, the newly open-sourced X algorithm, and a grounded debate on SaaS valuations, Brex, Figma, and whether AI is actually killing incumbents or just reshaping costs.

I'm a former creative director, 3x head of marketing, and founder of Vibe Your SaaS. After 20 years in Silicon Valley, devising new ways to get people to click, I now help early-stage B2B SaaS companies scale through GTM consulting. We use my proven frameworks and battle-tested methodologies so you can build a massive reputation, get leads, and close more sales. What startup doesn’t want that?

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