Howard Tullman doesn’t hedge. As a founder, investor, educator, and longtime pillar of Chicago’s tech scene, he’s seen cycles come and go. What he brought to this conversation wasn’t optimism—or cynicism—but clarity.
We talked about AI, startups, hiring, culture, valuation, Gen Z, and the post-VC era. What emerged was a leadership reality check: gritty, unsparing, and exactly what most people won’t say out loud.
Here are 10 takeaways that stuck with us:
1. Scut work wasn’t just grunt work—it was culture.
You learned how to pay attention by doing the things nobody wanted to do. That’s gone. Without it, companies are losing institutional memory, mentorship moments, and early-career development. AI is only accelerating the erosion.
2. You can’t teach work ethic. You can only hire for it.
The best founders Howard backed weren’t the smartest—they had grit. They didn’t need to be convinced that effort matters. They already believed it.
3. The new up is flat.
Valuations have stalled. Growth isn’t exponential anymore—it’s earned inch by inch. VCs can’t raise follow-on funds without exits. Meanwhile, founders are left building sustainable businesses that no longer fit the venture model.
4. AI is real—but only for the rule-based stuff.
Law, finance, compliance, code—AI is eating that world. But creative work? Not yet. We’re seeing high-quality output in narrow lanes, not broad innovation. The wins are in the infrastructure, not the imagination.
5. The platform tax is permanent.
If you’re building on top of LLMs, app stores, or any major tech layer, you're paying rent—forever. The myth of platform independence is dead. You either build narrowly and deeply, or get commoditized fast.
6. There’s no bench strategy anymore.
Hiring “just in case” is over. The best companies hire when there’s a real need, for a specific role, with clear outcomes. Anything else is a financial drag.
7. Founders are exhausted—for good reason.
They survived the pandemic, layoffs, capital freezes, and now face pressure to scale again. But many don’t want to risk that pain twice. The "growth at all costs" era has a hangover, and it’s long-term.
8. Venture is misaligned with what most businesses are now.
The era of chasing 10x outcomes on every bet is fading. Most great companies today are slower, steadier, and more grounded in real revenue. That’s not failure—it’s maturity. But the capital model hasn’t caught up.
9. Culture can’t be built through perks.
Dogs in the office, hybrid Fridays—none of it matters if there’s no shared mission or interdependence. Culture happens in the trenches, not in Slack channels.
10. Stop telling your kids you work to buy stuff.
One of Howard’s final points landed the hardest: if you want your kids to understand work, don’t tell them it’s about houses or vacations. Tell them it gives your life meaning. And then live that way.
Bottom line:
Founders can’t afford to chase illusions. The next era of leadership is about clarity, discipline, and alignment—no borrowed playbooks, no platform dreams, no venture fantasies.
You don’t need to grow at any cost. But you do need to know what you’re building, why it matters, and who’s in it with you.
