As a startup investor, I've seen many careers develop over the last 20 years and one of the worst patterns I see is: low expectations.

Some funding rounds close quickly, but many get stuck in a quagmire of legal work.

The death of SaaS has dominated tech news and discussion recently, and justifiably so, household names like Salesforce have already seen their stock price drop almost 30% this year.

It sounds like science fiction but the coding AI tools are now advanced enough that you can have dozens operating on your behalf concurrently.

Today, we’re talking about where to find angel investors.

Today, we’re talking about fundraising momentum.

Today, we’re talking about when to fire yourself.

It's been more than 10 years since we sold SendHub, but I still get weekly reminders of the damage the acquisition process did to my health.

When your startup fails, it's hard to let go and lots of founders try to save the last breath of their old company and roll it into a new one.

Today, we’re talking about the importance of growth to investors.

Today, we’re talking about founders making negative comments at the start of their pitch.

Today, we’re talking about founder tactics that may work but your advisors have to push back on them.

The new World of AI has changed investor expectations for startups and that is making survival more and more binary.

Today, we’re talking about following up.

In November 2018, PlanGrid, a SaaS startup in Construction, announced they were acquired by Autodesk for $875M.

With AI hiring drama all over the news, it's clear the rules have changed when it comes to Silicon Valley's talent wars.

If one of your co-founders leaves, it can be an incredibly rough time for you and the company.

In early 2025, I made 4 predictions about how AI would progress over the next 12 months, thus it's time to review my accuracy and make new predictions for '26.