Kishau Rogers

Issue 01 | August 5, 2025

Issue #01: Start Where You Are

View on the web →

Hello again.

You may have signed up years ago, or just last week. Either way, this is the official relaunch of my newsletter, and I’m glad you’re here.

A quick re-introduction: I'm Kishau (pronounced Kih-shaw). For over two decades, I’ve been a full-time tech entrepreneur, building solutions for hundreds of leading organizations and growing businesses through everything from bootstrapping to grant-funding to raising over $10 million in venture capital. This is where I share what I’ve learned and what I’m still learning about making big ideas real using what you have, where you are.

This space is for:

• People with the audacity to believe they can build something meaningful using what they already have.
• People who aren’t waiting for permission, perfect conditions, or outside validation.
• People building big ideas with limited resources, using their skills, creativity, lived experiences, and (sometimes) tech.
• People who don’t want to be boxed in by someone else’s algorithm, niche, or blueprint.
• People who want to own their work, shape their path, and make a living doing what they’re good at.

If that’s you, you’re in the right place. And if it's no longer a fit, no hard feelings, you can unsubscribe anytime using the link at the bottom of this email.
​
Lately, I’ve been in conversations with entrepreneurs and the entrepreneurial who were counting on traditional systems to build something new. The economy is uncertain, funding is slowing, and the usual formulas aren’t working.

In this first issue, I’m sharing a few insights and creative strategies to challenge your mindset, empower your instinct, and explore new ways to bring your big ideas to life, starting where you are.

If any of this is helpful, reply to the email and let me know what you think!

In this issue: ​

Insights On Downturns, Improv & Instinct 3 Ways to Challenge Your Thinking Behind The Scenes: Creative Practice Notes Collaging: Be Prepared Not Predictable Don't Miss! What If? Series Technique for Breaking Linear Thinking Tools & Talks Tools I'm Trying: Voice Note Automation Talk: Creating the Conditions for Big Ideas

Insights

On Downturns, Improv & Instinct

I’ve been thinking about creativity, specifically improvisation, as a key skill for navigating the current moment (waves around).

During the 2008 financial crisis, I was interviewed for a Wall Street Journal article about how entrepreneurs were navigating the downturn. The piece was titled “It Just Isn’t Working? Some File for Customer Divorce” because, for me, survival wasn’t just about cutting costs. It meant questioning everything that quietly drained resources, including underperforming services and even misaligned clients.

When you’re constantly navigating systems and other people’s playbooks, it’s easy to lose touch with your own instinct. There’s always a framework. A formula. An expert with 10 steps to get you from here to there.

But sometimes, the way forward has to come from you.

If you’re feeling stuck or uninspired, keep reading for a few strategies to explore.

Tips

3 Ways to Challenge Your Thinking

01 Redefine The Rules What or whose rules are you following, and are they still serving you? Notice where a process or playbook no longer fits. What would it look like to step outside those constraints? What would you do if you could change or ignore the rule entirely? ​ 02 Redefine "Product" There’s the product that reflects your long-term vision, and all the smaller ones in between. Sometimes, the product is the process: the insight, clarity, or data gained from collaborating, experimenting, or shipping. What would an iterative approach look like for you? How can each step provide value? ​ 03 Start with Enough What would you build if you knew, with certainty, that all you have is all you can use? Constraints can be a creative advantage. Start there.

BTS: Creative Practice

Be Prepared Not Predictable

I’ve started a Creative Practice series exploring how routine, hands-on work can sharpen thinking, shift mental models, and unlock new possibilities. This summer, I began a creative sabbatical to recharge, rebuild my creative muscle, and leave space for high-impact work. I recently revisited an old hobby by taking a collage workshop. It had been a while since I took a course, especially in visual art or mixed media. This post offers a behind-the-scenes look at preparing for class, exploring how structure, curiosity, and improvisation interact and why presence matters when plans fall apart.

Read More →

What If?

Breaking Linear Thinking

“What If?” is my new blog series exploring speculative scenarios that spark curiosity, imagination, and big-picture thinking. This post is inspired by skip-reading, a surrealist technique used by artist Frederick Sommer. By intuitively selecting words, the method disrupts linear thinking, clears preconceived ideas, and sparks creativity through unexpected connections. A shift in viewpoint can change how we see problems, make decisions, and determine what is real.

Read More →

Featured Tools Tools I'm Trying Voice to Text Workflow Automation

I use voice notes to capture thoughts for blog posts or daily work journals, especially when I’m on the go. Since I usually need to transcribe those notes later, I set up a lightweight system that does it automatically, using tools I already have. Now, when I record and save a voice note, it’s transcribed in the background. A few moments later, the transcript appears in a shared folder accessible from all my devices.

Tools:

• Voice Memos (or any voice recorder)
• Sync Folder (Dropbox, iCloud, or Syncthing)
• OpenAI Whisper + Python +(runs locally)
• macOS Automator (or Windows Task Scheduler)

Creating the Conditions for Big Ideas

I had the honor of opening Richmond’s 2025 Big Dipper Innovation Summit on a panel that explored what innovation really looks like in legacy industries like medicine. As a Virginia native and longtime Richmond resident, I shared how I launched Time Study here. But our growth was fueled by partners beyond the region, helping us scale to over 100 leading health organizations. That experience shaped my message: innovation isn’t just about invention. It’s also about creating the conditions for ideas to launch, grow, and thrive.