[Founders Blog] Shadow’s Jay - The AI Assistant Truly Understands You

Inside the Mind of a SaaS Founder: The Journey Behind Shadow

As the founder of Shadow, my journey into entrepreneurship wasn’t a sudden leap but rather a gradual realization fueled by a persistent problem I noticed in my professional life. Coming from a background in venture capital and big tech, I was no stranger to the fast-paced, meeting-heavy environments where productivity often took a backseat to administrative tasks. I saw how these meetings, meant to drive strategic thinking, were frequently bogged down by the need to take notes, summarize discussions, and follow up on action items. This inefficiency sparked an idea: what if an AI-powered assistant could handle these mundane tasks, freeing professionals to focus on what truly matters?

This thought was the seed that grew into Shadow, an AI meeting assistant designed to automate note-taking, summarizing, and follow-ups, allowing businesses to operate more efficiently and effectively. The goal was simple: to help people reclaim their time and channel their energy into driving their businesses forward.

A Day in the Life: Balancing Strategy and Execution

After energizing myself, I typically spend 15 minutes reading. This is to ensure that my brain is fully engaged, especially for tasks requiring deep focus. I then take a moment to reinforce my weekly and daily priorities, concentrating on the most critical tasks before reviewing the team's progress on Linear.

Mid-morning, I shift my focus to the product side of things. During this time, I review conversations I've had with users via Zoom calls or Slack repeatedly to ensure that I understand their problems, motivations, and needs with absolute clarity. This is the most crucial part of my day, so I schedule it when I feel most the most focused and energetic. I often take long walks, which help me process information and acts as brainstorming sessions for new ideas. (I highly recommend this if your brain ever feels foggy!)

After a brief lunch break, my afternoon is filled with meetings. These range from talking to users(again!) to syncing with the team on current projects.

Evenings are a time for reflection and planning. I review the day’s progress, jot down notes for the next day, and spend some time learning something new—whether it’s reading up on industry trends or diving into a book. I try to end the day by unwinding with family, striking that delicate balance between work and personal life.

The Tools That Powers My Day

Running a SaaS company requires a reliable set of tools to keep everything on track. For me, the following four are indispensable:

Shadow: Naturally, Shadow is at the core of my daily workflow. It keeps all my meetings organized, ensures that important discussions are accurately captured, and tracks action items so nothing slips through the cracks. Whether I’m talking to customers daily, investors occasionally, or conducting internal meetings, Shadow ensures that even as a terrible note-taker, I don’t miss the critical points. Post-meeting tasks are also a breeze—what used to take tens of minutes to extract key insights from user interviews can now be done with just a click!
Capacities: Capacities has become my go-to for personal organization. It’s where I now organize my reading notes, personal meeting notes, and more. Recently, I find myself using Capacities more than Notion or Obsidian for these purposes. Its opinionated structure offers a unique approach that I appreciate and even find inspiring for our own product development.
Raycast: Raycast streamlines my workflow by allowing me to quickly navigate and manage my tools with keyboard shortcuts and custom commands. While saving time on launching apps or searching files is important, what truly matters is how Raycast helps me avoid losing focus on unnecessary tasks, thereby conserving my mental energy.

Advice for Future Founders: Validate, Validate, Validate

If I could offer one piece of advice to future founders, it would be to validate your idea early. It’s easy to get caught up in the excitement of your solution, but it’s critical to ensure there’s a real market need for it. Engage with potential customers before you start building—understand their pain points, gather their feedback, and iterate accordingly. We did this by setting up one-on-one onboarding sessions with our early access users, which helped us ensure we were building a product they truly wanted and needed. The better you understand your audience, the more valuable your product will be.

The Toughest Decision: Pivoting for Success

In the journey of building Shadow, one of the toughest decisions we faced was pivoting our product direction. Originally, we started with a product known as Tape, an asynchronous messaging software designed for remote teams. While we still use Tape internally and have a small user base, we realized early on that the market we were targeting wasn’t as receptive as we had hoped.

This realization led us to make a difficult but necessary pivot. We decided to focus on a broader market where we saw a greater need for our technology—meeting management. This decision wasn’t easy, but it has proven to be one of our best. It allowed us to leverage our existing expertise while addressing a more pressing pain point in the market. The key takeaway? In entrepreneurship, resilience and adaptability are crucial. It’s a marathon, not a sprint, and the ability to pivot when necessary is often the difference between success and failure.

What I Wish I Knew: It Takes Time—Do What You Love

Over the past decade, I’ve dreamed of starting my own company, met with hundreds, if not thousands, of entrepreneurs, and witnessed the successes and failures of countless startups. But experiencing it firsthand has shown me that building a startup takes time and is far more challenging than I ever imagined when I was just on the investment side of things. The only way to endure this journey is to acknowledge these challenges and do something you truly love and enjoy. Cliche I know, but it stands true.

Every step along the way, from the initial spark of inspiration to the day-to-day grind, has reinforced the importance of staying adaptable, validating your ideas, and leaning on a strong support network. As we continue to grow and evolve, these principles will remain at the core of our mission to help professionals reclaim their time and drive their businesses forward.

Final Thoughts

The journey of building Shadow has been filled with challenges, tough decisions, and invaluable lessons. From the initial spark of inspiration to the day-to-day grind of running a company, every step has reinforced the importance of staying adaptable, validating your ideas, and leaning on a strong support network. As we continue to grow and evolve, these principles will remain at the core of our mission to help professionals reclaim their time and drive their businesses forward.

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