Dear Readers,

Three founders, three months, under $100,000 - and a product that already generates revenue. SkipUp is proving that the AI era has fundamentally rewritten the startup playbook. The company built an AI-powered executive assistant that handles scheduling through a brilliantly simple mechanic: you cc SkipUp into an email, and it books the meeting for you. No calendar links, no back-and-forth, no friction.

What makes this more than just another scheduling tool is the ambition behind it. Co-founders Sasha and Dheer see scheduling as the entry point to something much bigger - a personal AI agent for everyone. Their insight: people don't have too many meetings, they have the wrong ones. SkipUp doesn't just coordinate calendars, it brings the context awareness of a human assistant without the cost of hiring one.

In today's edition, we're dedicating the entire issue to an exclusive interview with the founders of this exciting AI product.

As a bonus, SkipUp has created an extra link for our readers, which allows users to create 20 meetings for free: Free SkipUp Subscription [CLICK]

Let's dive in!

All the best,

Kim Isenberg

Kim: Let’s start with the simple version. What exactly is SkipUp and what does the product do for the user?

Sasha: We see a world where every person has their own executive assistant. There’s a network effect when everyone has their own personal agent. We want to give every person access to that so they don’t spend all their time scheduling, living in their inbox, or coordinating logistics. Scheduling is an important part of this because it’s where intentions in the AI world manifest in a structured way with other people. That’s why we started there.

Kim: You mentioned executive assistant. Who is the core user today for SkipUp?

Dheer: We’re seeing anyone with a busy schedule and anyone who needs to schedule meetings 24/7. That ranges from account executives and salespeople all the way to founders and CEOs with small teams. Anyone living in their inbox who feels the pain of time zones, sending calendar links, or coordinating schedules. It’s actually a pretty broad set of users. Our first customers were software companies, venture capital firms, and teams that needed to schedule meetings constantly.

Sasha: One thing we’re also seeing is that many of the people adopting SkipUp are the ones driving AI adoption inside their organizations. CEOs and CROs use it themselves to show it works, and then the rest of the organization follows. So the change is often top-down, but the adoption can start bottom-up from individuals who feel the pain first.

Dheer: Usually it starts with someone saying, “I need an executive assistant but I can’t afford one.” SkipUp becomes the entry point. It’s one of the lowest-cost ways to begin an AI transformation without launching a large initiative.

If you’re a decision maker at your company, you need to be on the bleeding edge of, well, everything. But before you go signing up for seminars, conferences, lunch ‘n learns, and all that jazz, just know there’s a far better (and simpler) way: Subscribing to The Deep View.

This daily newsletter condenses everything you need to know about the latest and greatest AI developments into a 5-minute read. Squeeze it into your morning coffee break and before you know it, you’ll be an expert too.

Subscribe right here. It’s totally free, wildly informative, and trusted by 600,000+ readers at Google, Meta, Microsoft, and beyond.

Kim: It sounds small on the surface—just scheduling—but clearly you believe it’s a much bigger problem. What made you think it was important enough to build a company around?

Dheer: The concept started with agendas. We noticed companies often know what their teams did last week, but they don’t know what people intend to do in the future. Management reporting is usually backward-looking. Scheduling turned out to be a point where you can observe and influence how people spend their time.

Dheer: Another way to explain it is that we originally planned to build something like an ERP. We needed a way to enter the market and manage change, so we spoke to founders and CEOs about their biggest problems. Many said they were spending too much time in meetings and not getting anywhere. We started building meeting agendas to help with better planning, but the real problem turned out to be different.

Dheer: People weren’t having too many meetings—they were having the wrong meetings. They wanted to meet customers, prospects, and people who could help grow their business, but they weren’t getting traction there. Instead they filled their calendars with internal meetings. Scheduling became the entry point to solve that problem. Both of us have worked with executive assistants and chief-of-staff roles before, so the problem was familiar.

Kim: So it’s mainly about efficiency?

Sasha: Exactly. Scheduling and meetings are the operational cadence of a business. How efficiently people exchange information becomes the operating system of an organization. We saw scheduling as the smallest wedge we could enter with. If we get this right, the operational efficiency of teams improves massively.

Dheer: Think about a salesperson working a big deal. While doing that, they still need to maintain their pipeline and follow up with many people. That takes effort. If SkipUp handles that coordination, they can focus on the deal while their pipeline continues moving forward.

Kim: Before we go deeper into the technical side, let’s go back to the beginning. How did the idea for SkipUp come together, and how did you decide to build it together?

Sasha: Dheer and I used to work together. We were essentially the “dumpster fire team.” When something went wrong, we were the people crazy enough to tackle it but capable enough to pull it off. We were always fascinated with the idea of the operating system or ERP of businesses and how that would translate into the AI world.

Sasha: We started doing discovery interviews with founders and executives. Dheer looked at the future architecture from the ERP perspective, while I looked at it from a venture capital perspective: what is the smallest wedge we could start with? Over time we realized those perspectives overlapped. We started ideating, and eventually we said, “Let’s try it.” We incorporated through Stripe Atlas and suddenly it was a real company.

Kim: Did the original version look different from what SkipUp is today?

Sasha: Yes, we pivoted. The first version focused on meeting preparation and agendas. But the behavioral change required there was too big. We wanted something intuitive where someone could understand and start using it within 30 seconds.

Sasha: People who already prepared agendas didn’t need help, and people who didn’t prepare agendas didn’t see it as a problem. So we realized we needed to earn the right to do agendas by first solving scheduling extremely well. By doing that we gather context along the way. That path is much more scalable.

Kim: Why is now the right time for a product like this? What changed recently?

Dheer: Scheduling is extremely complex. You have time zones, preferences, multiple calendars, and personal commitments that don’t appear in calendars. Historically the solution required heavy human involvement. Technology helped a little, but humans still handled most of it.

Dheer: What changed recently is that large language models have become much more capable. They can process more context, follow mental models, and reason through nuanced situations. Those advances make it possible to automate scheduling at a much deeper level than before.

Sasha: We’ve also learned how to build robust frameworks around these tools. Because of that, our three-person team has produced the equivalent output of a 20- to 40-person engineering team. That’s how we went from concept to revenue so quickly.

Kim: What differentiates SkipUp from existing scheduling tools?

Sasha: Our best users are former Calendly power users. They shared links everywhere and eventually their calendars were destroyed—meetings from morning to evening with no logic behind them. They needed the context awareness of a human assistant but didn’t need a full-time person. SkipUp provides the structure of a booking tool with the awareness of an assistant.

Dheer: Traditional booking tools work well only in simple one-on-one situations. They break down with power dynamics, multi-person meetings, or follow-ups. Someone usually ends up acting as the coordinator manually. SkipUp removes that friction and automatically follows up at the appropriate cadence.

Sasha: It also improves the experience. If you send someone a booking link with multiple steps and forms, that’s not a great experience. With SkipUp it can be as simple as someone saying “3 PM works for me.” The system handles everything behind the scenes.

Every day, 4.5 million readers turn to 1440 for their factual news fix. We sift through 100+ sources to bring you a complete summary of politics, global events, business, and culture — all in a brief 5-minute email. No spin. No slant. Just clarity.

Join for free today!

Kim: Let’s talk about the technical challenges. What makes something like this difficult to build?

Dheer: There are multiple layers. First, the system has to behave like an expert executive assistant with decades of experience. It must understand context, priorities, and nuance. Second, large language models are non-deterministic—you can’t always predict the exact output. Our system adds guardrails and deterministic processes so the behavior is reliable.

Kim: How do you prevent it from losing context?

Dheer: We train the agent to extract only the relevant mental models for the situation it’s in. Instead of loading everything, it identifies the relevant scenarios from a large library and acts accordingly. It’s similar to how humans recall experiences from memory.

Sasha: You can think of it as a library of experiences. The system recalls how to handle similar situations based on past patterns.

Kim: What were the earliest signals that this was working?

Sasha: Usage. We focused on whether people actually used the product and whether it genuinely helped them. When users began telling others about it and word of mouth started spreading, that was the strongest signal.

Dheer: We even had users asking how they could pay before we had fully implemented billing. That’s when we realized we needed a payment system quickly. We also have users who talk about SkipUp constantly—even showing it to friends at bars.

Kim: Was there a moment when you realized the product felt special?

Sasha: Some users treat it like a party trick. They introduce SkipUp in meetings and people are surprised they have an executive assistant. For people outside the AI bubble, it looks like magic.

Dheer: Sometimes people even treat SkipUp as if it’s human. Someone emailed us asking if they could meet SkipUp in person.

Kim: What surprised you most about building the company?

Sasha: The velocity. The last few months have been unbelievable. We incorporated a company, built a product, set up accounting and compliance, and reached revenue—all for under $100,000. That would have cost millions a few years ago.

Dheer: Another big change is the feedback loop. Previously a product request could take months to reach engineers through multiple layers of management. Now the product itself detects requests, generates tickets, and workflows can produce code in minutes.

Kim: Where do you see this going in the future?

Sasha: We’re riding a massive wave of AI capability. It’s difficult to predict exactly where it leads. We believe every person will eventually have a personal AI agent, and scheduling is a powerful entry point. Beyond that, it could evolve into something like an operating system for companies or something entirely new.

Dheer: Relationships will still exist in business. Meetings will still happen. Technology that facilitates those interactions will remain valuable.

Kim: Any final advice for founders watching this?

Sasha: Many founders still build companies based on outdated assumptions about funding and team size. Today you can build a company with very little capital. If there was ever a time to try building something, it’s now.

Dheer: And of course, try the product. Play with it and see what it can do. That will give you your own ideas about what’s possible.

Why it matters: SkipUp demonstrates that AI-native startups can reach revenue with tiny teams and minimal capital, reshaping how companies are built. It also signals that scheduling — long considered a solved problem — is becoming the strategic entry point for much deeper AI integration into daily work.

Sources:
🔗 https://app.skipup.ai/sign-up?promo=SUPERINTEL