How This Entrepreneur Sold His Startup To Dropbox For $165M | Russ Heddleston

Imagine thinking your startup is doomed, only to be acquired for $165M.

On this episode of High Stakes, Russ Heddleston shares the wild ride that led to DocSend’s $165 million acquisition by Dropbox.

The absurd part? His investors doubted the product.

Russ was left asking everyone, “Does anyone want to buy this company?” and heard nothing but no.

Then Dropbox saw the value and made an offer of $165 million.

Russ recalls, “We beat the IRR of every fund that invested in DocSend.”

In this chat with Managing Partner Paige Soya, they discuss:

• funding
• exits
• Russ’s next venture, Distill (hint: think Wikipedia, but for company and people summaries).

Connect with us here:

1. Russ Heddleston:   / heddleston  

2. Paige Soya:   / paigesoya  

3. K Street Capital:   / kstreetvc  

00:00:00 Trailer
00:00:51 Introduction
00:03:49 Selling Docsend to Dropbox for $165M
00:06:58 How Docsend Struggled to Sell
00:10:50 Why Docsend Chose Dropbox Over Higher Offers
00:15:23 Could Docsend Have Been Worth $1 Billion?
00:17:58 Negotiate harder when selling
00:22:21 Building DocSend Without a Clear Exit
00:25:24 DocSend’s Unbeatable Advantage
00:26:40 Advice for Founders on Exit Strategies