Rob Lennon

Most creators, coaches, consultants, and solo business owners know AI is powerful — but they’re trying to learn it by wading through hype, half-truths, and overly technical tutorials built for engineers, not entrepreneurs.

And that's a problem because those flashy demos and one-size-fits-all prompts ignore what actually matters: practical, repeatable business outcomes. They don’t teach you how to think with AI... they just throw more tools at you.

Because of that, people end up feeling overwhelmed, unsure, or worse: they waste hours tinkering without anything meaningful to show for it. AI becomes another shiny object instead of the time-saving, clarity-creating tool it could be.

Which means you stay stuck in the loop of knowing AI should help your business, but not knowing how to make it stick, missing out on the dozens of small daily wins that could actually move the needle.

On the other hand, what I do is cut through the noise and show you exactly how to use AI in ways that fit your business, your brain, and your bandwidth.

I give you high-leverage prompts, real frameworks, and live walkthroughs that make it easy to start using AI — not just understanding it — whether that’s creating content, refining offers, or automating tasks...

So that you build AI into your actual workflow in small but mighty ways that save time, spark clarity, and support the work you’re already doing — not add more complexity to it.

As a result, you become the kind of business owner or operator who’s not just keeping up with AI — you’re benefiting from it. Quietly outpacing others not with gimmicks, but with smarter systems, clearer messaging, and more momentum — powered by real-world AI you can actually trust to help with your most important work.

Solopreneur Coach / Consultant

Supporting solopreneurs, founders, and agency owners with coaching and consulting on audience growth and audience-driven business systems to drive $$$ at a fraction of the cost of traditional marketing.

I help growth-stage tech CEOs and CTOs turn ambitious visions into consistent execution, so they can scale with confidence and keep their teams fully aligned.

Most of my clients are brilliant builders stuck in "hero mode," making every decision, fixing every fire, and slowing down their own growth. I help them become high-leverage executives with the systems, team structure, and clarity to lead at scale.

Clients include OpenAI, Automattic (WordPress), ASML, Heap Analytics, and Tealium

- OpenAI: Helped productize and operationalize GPT-3 during rapid expansion
- Automattic: Coached VP of AI and VP of Product to launch an AI-native strategy and unify WooCommerce, Jetpack, and Domains
- ASML and Tealium: Led company-wide Agile transformations across product, engineering, and operations
- Sendlane: Tripled retention and scaled to 10.4B emails per year through customer-driven product systems
- Heap: Guided EVP through hypergrowth, hiring over 300 engineers in less than 6 months, with 90% retention
- Sempre Health: Supported CEO and CTO through $20M+ Series B+ with strategic hiring and founder growth

What we work on together:
- Building high-trust, self-managing teams
- Clarifying product and growth strategy
- Transitioning from founder to executive
- Leading with clarity, calm, and control

If you're a founder, CEO, or CTO ready to scale your leadership and your company, let’s talk.

To book a Clarity Call, DM me or book here: https://calendly.com/emweiss/30min

Eric Weiss

Welcome to the new year everyone, let’s talk about goals. You are 50% more likely to accomplish a goal if you announce it publicly, so let’s share!

Here are my goals for 2026:

1. Help the founders I coach on average raise $10M in capital and 2x their revenue.

2. Coach 2 new scale-stage founders, and help them raise $10M in capital and 2x their revenue.

3. Launch the San Diego chapter of VC Village, host 6 exclusive investor events, and make them so cool that we have a waitlist to join.

4. Launch a San Diego based Founder Circle, and help at least 5 seed-stage founders find Product-Market Fit and raise at least $3M in capital.

5. Finish my last year as President of Design Forward Alliance with a bang, by hosting the highest attended (and funded) San Diego Design Week ever.

6. Step into a leadership role with Startup San Diego, and help lead the largest community of entrepreneurs in the region.

7. If that isn’t enough to keep me busy, find a Fractional Chief Product Officer role at a mission-driven tech company focused on health, community, or the environment.

Now your turn!

Strategic Advisor and Performance Coach for CEOs and CTOs | Clients: OpenAI, Automattic, ASML, Heap | Product Strategy, Leadership, Growth Systems

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