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The First Pitch That Actually Landed

All, Business, Communication, Startups / 3 June 2025

Reading Time: 3 minutesI used to pitch like I had something to prove. Then I told one honest story about a real problem, and that’s when the pitch finally worked.

The First Pitch That Actually Landed Read More »

Photo of open hands with 'Yes' and 'No' written on the palms, expressing choice and diversity.

When to Say No to an Investor

All, Business, Startups / 27 May 2025

Reading Time: 3 minutesEvery founder gets told to chase capital. But sometimes, the smart move is to walk away. This post is about how to say no and why it matters.

When to Say No to an Investor Read More »

Stunning view of Golden Gate Bridge partially covered by fog with clear blue sky.

Why Investors Say No

All, Business, Startups / 19 May 2025

Reading Time: 3 minutesMany founders pitch the dream. Investors want the details. This post explores why good ideas still get passed on and what to do differently next time.

Why Investors Say No Read More »

Reflective image of shoes and person in muddy puddle on an unpaved road.

When the Deal Isn’t a Deal

All, Business, Startups / 13 May 2025

Reading Time: 2 minutesWe wanted to invest. The team was solid. But the agreement didn’t hold up. This is what founders need to know before asking for money.

When the Deal Isn’t a Deal Read More »

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Where Does Your Revenue Really Come From?

All, Business, Startups / 2 May 2025

Reading Time: 3 minutesYou made money. Great. But do you know where it came from—and if you can do it again? This post is about turning early wins into something that lasts.

Where Does Your Revenue Really Come From? Read More »

Colorful green food truck with umbrella, offering street food in Tokushima, Japan. This is an example of what some startups can be.

Startups Aren’t Just for Tech Bros. Seriously They’re Not.

All, Startups / 22 April 2025

Reading Time: 2 minutesWe’ve been taught that startups mean tech and scale. But there’s more to the story. This is for the builders who are figuring it out as they go.

Startups Aren’t Just for Tech Bros. Seriously They’re Not. Read More »

Explore the vibrant neon-lit train station platform in Toledo at night, showcasing urban architecture.

Why Startups Always Underestimate Time—and How to Fix It

All, Startups / 7 April 2025

Reading Time: 3 minutesMost founders plan for money, but not for time. Here’s how timeline slip creeps in, what it costs you, and how to build smarter, more realistic roadmaps.

Why Startups Always Underestimate Time—and How to Fix It Read More »

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The Trouble with Perfect Startup Projections

All, Startups / 31 March 2025

Reading Time: 2 minutesStartup forecasts that only go up and to the right aren’t helpful. Here’s why clean models fail—and how to make yours a tool, not a fantasy.

The Trouble with Perfect Startup Projections Read More »

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My Blog

Reflections | Strategy | Real Talk

This is where I share what I’m noticing in the work—things that come up in conversations with founders, questions we keep circling back to, and tools that help cut through the noise.

Sometimes it’s about clarity. Sometimes it’s mindset. Always grounded in real-world experience.

Thanks for reading—I’m glad you’re here.

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Hi there! I am Os Ishmael. Welcome!

I care about helping people build things that matter—and making sure they stay steady while they do it.

Over the years, I’ve worked with founders, teams, and organizations trying to bring purpose into their work. Not just the big mission stuff, but the day-to-day choices, the clarity, the conversations that move things forward.

That’s the part I love: helping you think clearly, communicate simply, and stay aligned with what you’re really trying to build.

Fitness is a big part of how I stay grounded—running, lifting, moving. It keeps me steady, and I bring that same mindset to the work: focus, consistency, small wins that stack up.

This work isn’t about hype. It’s about showing up, staying true to what matters, and building with intention.

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I’m not into buzzwords. If you’re looking for a consultant who’ll nod along and tell you to “scale fast,” I’m not your person. But if you want a thoughtful partner who can help you build something solid—and who actually listens—let’s talk.

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