On financing/non-cash transactions & spacing payments across multiple years (to de-risk or acquire something larger)

via @rolandal (thanks for the email)

It’s honestly super hard (mostly due to lack of speed) unless you have a really strong lender relationship

Like I’m at the point where my lender knows what my investment style is and what kind of deals I even look at. He knows that my investment criteria and his lending criteria are aligned, so in many ways I’m “pre-approved” for just about any amount, and actually getting things in motion is just a matter of bureaucracy. Even with such a well-oiled relationship, stuff still takes forever

One time, I was trying to buy a Shopify app. I reached out to a lender for $300k. They asked me for a quality of earnings (typically 30+ page report) to ensure the Shopify PayPal payouts were legit 🤦‍♂️