Introducing "Tales from the Trenches"

By David Stein

After 20+ years in tech, I'm launching a column covering building and scaling companies. Hard-earned truths about what actually drives growth and success.

“Tales from the Trenches” will cover one key issue we’ve recently encountered and collaborated on with founders, investors, or policymakers.

Why am I doing this?

In building and backing multiple technology companies that have rapidly grown from 0-100M+ in ARR, achieved 1B+ valuations, and expanded globally, I’ve engaged on many issues that may appear to be new and novel to the startups facing them, but actually represent an expected challenge, pattern, or plateau that we’ve seen or experienced and successfully navigated.

Instead of keeping these conversations to 1:1s, by sharing more broadly, I can help a larger group of founders and company builders see around corners, avoid costly errors, and achieve their goals faster as they build world-class companies.

We need more direct feedback and information on what it really takes to succeed in tech. No corporate speak, no sugar-coating — just honest insights based on what I've seen work and fail in the real world.

From recent conversations I’ve had, I'll address in my first few posts:

- Policy and ecosystem changes could move the needle for Canadian tech

- Common mistakes first-time founders make moving beyond founder-led sales

- How companies are positioning their AI solutions to show value and win deals

Some of my views might be controversial. I'm okay with that. I’m not trying to be popular — I’m trying to share insights that have worked, spark meaningful conversations, and help founders go faster.

Looking forward to the conversation.

David