My Love-Hate Relationship With Bill.com

And now for a few words on that most painful yet critical of startup topics, billing and payments!

Working on billing and payments feels incredibly far from strategic objectives like product and sales. It’s not something that differentiates one company from another. And yet it’s critical to the ongoing operations and success of a business.

Most recently, a company I’m closely involved with starting using Bill.com.

The company was really looking for was a simple way to pay everyone electronically, which seems straight-forward enough.

First up were the services offered by the bank. Everything had to be manually entered into the bank web site and then sync’d to QuickBooks. Plus, the mechanisms for synchronizing with QuickBooks required a download and… well, that was enough of that.

Soon came Bill.com. Here’s what I love:
- Signup is quick
- The site is fast
- Entering vendors is easy
- Vendors can enter their own info to get paid electronically

Here’s what I hate:
- No way to run payroll right from within Bill.com. This has to be done separately. No problem if you have hundreds of employees, but a real PITA if you only have a few.
- Signup is confusing for vendors because the site is terse on instructions and next steps.
- Roles are limited. Suppose I want to have someone enter bills to be paid, but not have visibility into other bills that have been paid. There’s no easy way to do that. And just finding where to setup new roles is hard to do.
- No easy import function. Can’t upload a CSV or Excel file with items to be paid.
- Every bill has to be entered manually. While a user can forward bills to the system via email, one can’t specify the amount due and have that automatically entered into Bill.com. So someone still has to enter the amounts.

Not really a Bill.com issue, but a more general one—the company still has to work with a number of different web sites and repositories to run the business—from the bank account to QuickBooks to Paypal to Bill.com. But it would be great if it all could just happen in one place.

I never thought I’d find myself writing a passionate blog post about invoicing and payments. But Bill.com is a big step in the right direction—I just hope the company will take a few more steps to make payments, invoicing and accounting much, much easier!

Why Startups Fail: And How Yours Can Succeed

Most startups fail. That’s why when Jeff Olson at Apress (publishers of Founders at Work) approached me about turning my Why Startups Fail blog post into a full-fledged book, it was too good an opportunity to pass up.

Why Startups Fail: And How Yours Can Succeed is now available in both eBook and paperback editions on Amazon and elsewhere.

By way of background, in May, 2008, I wrote a popular and controversial blog post, Why Startups Fail. Venture capitalist Brad Feld called it a great post. Jason Fried of 37 Signals disagreed with several of my points. Dave McClure and dozens of others provided insightful thoughts and comments.

Over the past 10+ years, I’ve founded five startups, bootstrapped and raised millions in venture capital, had several successful liquidity events, and been a VC. During that time, I’ve gained a unique perspective on what makes startups succeed—and the avoidable mistakes that make them fail.

I hope this book will provide you not only with excellent reading but also with key insights that will help make you, and your startup, a huge success.