David Barrett. He started programming at the early age of 6 and has been inspired to become an expense reporter ever since. He attended the University of Michigan where he worked in a virtual reality lab before moving to Texas to write a 3D graphic engine for the industry. Then, he moved to California to join a name that is probably familiar to many of you, Travis Kalanick, in building a peer-to-peer file transport technology called, Red Swoosh, which was acquired by Akamai in 2007. In 2008, David left that company to start Expensify—where he is today—and he’s trying to figure out the world’s frustrations, one expense report at a time. Famous Five: Favorite Book? – The Innovator’s Dilemma What CEO do you follow? – Travis Kalanick Favorite online tool? — G Suite How many hours of sleep do you get?— 6-8 If you could let your 20-year old self, know one thing, what would it be? – “I wish I had dropped out of college”   Time Stamped Show Notes: 01:13 – Nathan introduces David to the show 02:36 – David was working on a debit/credit card idea and the banks weren’t happy with it 02:50 – Expensify is the corporate card for the masses 03:08 – David got into the space when there was so much room for disruption and pain points 03:40 – Travis’ first company is called Scour, which is an early file sharing network that got sued 04:06 – When David got into Red Swoosh, Travis was the only guy there 04:48 – David thinks that Travis is very articulate in communicating his vision 05:12 – David had equity from Red Swoosh 05:31 – Red Swoosh didn’t have a big exit 06:14 – Expensify charges $9 per active user per month 06:20 – Expensify is a mobile app—you take a picture of your receipts and the app will read all the details on the receipt, automatically 06:29 – The information will then be categorized, sent to your account, and you’ll get reimbursed the next day 07:10 – The company is only paying the active users 07:29 – Expensify’s price points are $5 and $9 07:40 – David started Expensify’s idea after Red Swoosh’s acquisition 07:56 – David left Akamai in 2008, then he worked on Expensify 08:00 – Expensify’s official launch is 2008 08:05 – Expensify’s team size is around 110 08:18 – Expensify has raised capital 08:27 – Expensify has raised a total of $25M 08:36 – Expensify has been a break even business for a long time 08:39 – “We grow primarily through revenue” 08:52 – The vast majority of Expensify’s growth is through self-finance 09:54 – The business itself is breaking even, but they’re always raising and experimenting on big experiments 10:31 – There are about 25K companies who use Expensify 11:03 – There are millions of individuals who use Expensify, too 11:32 – 10% of Expensify’s user base are paying customers 10:43 – 10% of 4.5M are paying customers 12:12 – “Churn is complicated” 12:33 – Expensify has a net negative revenue churn 13:05 – Expensify doesn’t advertise and they have 100% organic traffic 13:37 – Expensify had a few fundraising rounds 13:41 – In 2008, they had their first $1M round 13:43 – They did a few more in a couple of years 14:25 – David doesn’t talk with investors and hasn’t talked with them in years 15:27 – Expensify is something totally different from Salesforce 15:53 – Expensify doesn’t have salespeople 16:16 – Expensify’s primary revenue generator is their support team who follow up on deployments 16:43 – Pricing has been difficult and Expensify is still working on it 16:53 – Expensify was originally free and customers didn’t understand why 17:18 – David thought they needed a reasonable price point 17:31 – After choosing a price point, people became more comfortable and trusting 17:51 – Expensify’s competitors followed their pricing 18:37 – Expensify’s focus is on mastering the dynamics 19:06 – David thinks that, realistically, their pricing should be much higher 19:34 – David is planning on increasing their pricing 19:52 – “Because we don’t need the money, we’re focused on something else” 19:58 – “Maintaining an incredibly low price right now for the industry actually helps keep the competition out” 20:29 – People find Expensify through word-of-mouth 20:51 – “All of our emphasis is on building a product in a brand that generates an incredibly strong word-of-mouth” 21:34 – 99% of Expensify’s traffic is people searching for us 21:40 – The Famous Five   3 Key Points: Adding a paid option to your product can actually make your customers more confident in your product. Word-of-mouth is one of the best and cheapest ways to grow your traffic and client base, but your business has to be valuable for people. A college degree is NOT the only road to success.   Resources Mentioned: The Top Inbox – The site Nathan uses to schedule emails to be sent later, set reminders in inbox, track opens, and follow-up with email sequences Organifi – The juice was Nathan’s life saver during his trip in Southeast Asia Klipfolio – Track your business performance across all departments for FREE Acuity Scheduling – Nathan uses Acuity to schedule his podcast interviews and appointments Host Gator– The site Nathan uses to buy his domain names and hosting for the cheapest price possible Audible– Nathan uses Audible when he’s driving from Austin to San Antonio (1.5-hour drive) to listen to audio books Freshbooks – Nathan doesn’t waste time so he uses Freshbooks to send out invoices and collect his money. Get your free month NOW Show Notes provided by Mallard Creatives