BCC Protection


At Opendoor, there’s a healthy default towards transparency. While we are a Slack-heavy company, we still use email a good amount especially for communicating with external parties. However, email and transparency aren’t something that go hand-in-hand, unless you’re Stripe I II

Luckily, BCC can be used to build openness and keeping relevant internal parties in the loop when emailing external parties. I never really used to BCC or get BCC’d until I worked here but now it’s become indispensable. That being said, getting BCC’d or BCC’ing somebody has also become one of my biggest fears. 

  • What if I reply all?  ?
  • What if the person who I BCC’d doesn’t realize they’re BCC’d, and they reply all? ?
  • What if the other people then realizes that I was BCC’d and is now super confused? ?

Every once in a while my fear comes true…Case below: I BCC’d “C” but they ended up replying-all! 



Email clients should build BCC Protection that would reduce the chances of ending up in one of the above scenarios in two steps: 

  1. Visual Cues: Callout being BCC’d on particular email. Use a color to clearly signal to the reader that, yo friend, you’ve been bcc’d. please remember that” 
  2. Confirmation on Send: Additionally, if the user attempts to reply to any additional parties apart from the email address that bcc’d them, throw the user a warning when they hit send. You might save a partnership or somebody some embarrassment

We’ve already gotten used to this when the word attachment is mentioned but there’s no attachments on the email…this would be a nice addition to that. 

Note: I would usually send this note to my good friends at Polymail  but I’m actively attempting to give them a break from my ramblings  

DBX’s S-1: Bottom’s Up SaaS


The first companies that come to mind as one thinks about users as the gateway into an organization are Dropbox and Slack. While their individual mechanics are different, they’re very good at getting users to join orgs that then pay. ​In addition to building a 10x better product, they have the strong brand & community that it takes to be installed on day one of a new org; something which is incredibly difficult to nail down and continues to be a holy grail of the fabled land & expand distribution strategy. 
  • Dropbox: Win the user in single-player mode and then become the first option as a user thinks about a service for their org (multiplayer mode).
  • Slack: Win the org on day one because there’s zero friction to start on multiplayer mode. Get users as company’s get bigger and people move companies. ​​

(More on Single-Player vs. Multiplayer here on CDixon’s blog)

On the topic of distribution channels for new products, Peter Thiel  refers to a “sales deadzone” that sits in between needing sales people for complex transactions & advertising for simple ones (no sales people).  Eventually, as companies get big they develop multiple channels but it’s critical that there’s a product-channel pathway that works in the early-days for it to succeed and this bottoms up distribution approach works very well in this deadzone as it offers distribution that can scale from the early days for products that sit in between the two ends of the spectrum. (as most productivity related tools do)

In light of the S-1 being shared for Dropbox’s IPO, here’s a few tidbits related to this approach. 

At Dropbox’s Launch: 

  • There are some unannounced viral parts I didn’t get to show in there it;ll be a freemium model. up to x gb free, tiered plans above that. dhouston, 2007


At IPO: 

The bottoms up approach continues to be a core focus for the business even after 10 years.

What Sets Us Apart
Viral, bottom-up adoption

  • Our 500 million registered users are our best salespeople. They’ve spread Dropbox to their friends and brought us into their offices. Every year, millions of individual users sign up for Dropbox at work. Bottom-up adoption within organizations has been critical to our success as users increasingly choose their own tools at work. We generate over 90% of our revenue from self-serve channels—users who purchase a subscription through our app or website.

Industry Trends in Our Favor
Individual users are changing the way software is adopted and purchased

  • Software purchasing decisions have traditionally been made by an organization’s IT department, which often deploys products that employees don’t like and many refuse to adopt. As individuals increasingly choose their own tools at work, purchasing power has become more decentralized. A 2017 IDC report noted that new devices and software were being adopted at a faster rate by individual users than by IT departments.

Our Growth Strategy
— Early virality with a free user base continues to be a part of the plan to pay dividends  
Increase adoption and paid conversion

  • We designed Dropbox to be easy to try, use, and buy. Anyone can create an account and be up and running in minutes. We believe that our current registered user base represents a significant opportunity to increase our revenue. We estimate that approximately 300 million of our registered users have characteristics—including specific email domains, devices, and geographies—that make them more likely than other registered users to pay over time. Substantially all of our paying users share at least one of these characteristics. We reach our users through in-product notifications on our website and across hundreds of millions of actively connected devices without any external marketing spend. We define an actively connected device as a desktop, laptop, phone, or tablet on which our app has been installed, and from which our app has been launched, and made a request to our servers at least once in the most recent quarter.

Risks Related to Our Business and Our Industry
Our lack of a significant outbound sales force may limit the potential growth of our business.

  • Historically, our business model has been driven by organic adoption and viral growth, with more than 90% of our revenue generated from self-serve channels. As a result, we do not have a significant outbound sales force, which has enabled us to be more efficient with our sales and marketing spend. Although we believe our business model can continue to scale without a large outbound sales force, our word-of-mouth and user referral marketing model may not continue to be as successful as we anticipate, and our limited experience selling directly to large organizations through our outbound sales force may impede our future growth. As we continue to scale our business, an enhanced sales infrastructure could assist in reaching larger organizations and growing our revenue. Identifying and recruiting additional qualified sales personnel and training them would require significant time, expense, and attention, and would significantly impact our business model. Further, adding more sales personnel would change our cost structure and results of operations…

Growth & Conversion Metrics 

to Summary:

  • 500m Registered Users
    • 100m signed up in 2017 (20% of total)
    • ~2% over all paying customers 
  • 11m Paying Users
    • 2.2m started paying in 2017 (20% of total)
    • 30% Business Plan, 50% Individual for Work, ~20% Individual 
    • $111.91 ARPU 

​User Growth: We can see that the user base continues to grow at a rapid pace; 25% in 2017.  The number of paying users has grown at the same rate as well which means that the conversion rates have likely stayed the same for new customers on an annual basis, assuming that customers who haven’t paid in their first year drop to a near zero chance of conversion. However, the S-1 filing gives little insight into what the consumer conversion curves look like so I’ll look to track these in future filings. 

Conversion Channels: 90% of DBX’s current conversion comes from self-serve. This is remarkable and flies the other way of BOX. 

Conversion: Currently about 2% of DBX’s users are paying customers. The parallel to this is BOX where 17th of their 57mm customers are paying customers. It’s hard to parse out the cost of supporting the free users because DBX doesn’t include this in their CAC (26% of Rev) while BOX does (63% of Rev) but given that their gross margins have nearly 2x’d one can assume that the cost of free users in ratio to their conversion rate works out well for the company. 

Overall, this looks incredibly impressive for a company very rooted in the idea of bottoms up and is doing relatively well compared to BOX. In the long run, their bottoms up approach will be compared to Atlassian/Slack as opposed to their storage competitor. 



What got you here won’t get you there.

As has been pointed out in multiple discussions in-person and twitter: DBX’s S&M costs will trend towards BOX’s as they dive deeper into getting bigger corporate contracts via outbound sales. 

However, there’s a dark horse with creative tools like Paper & Showcase which have strong network effects that could continue to drive low CAC biz user growth (vs. personal user growth that was the first wave). Also, there’s still a big pool of free users (personal) who don’t have a paid sub via a company converting but these customers will be harder as time goes on & DBX will sell like how Box sells. 

This will be fun to see and whether it’ll be able to average out the increasing costs alluded to above. Personally, I continue to be incredibly excited about bottoms up adoption and how it plays out in the long-run and how it stacks up against two other wonderful bottoms up SaaS businesses TEAM & Spotify. 

P.S This is a good read on SaaS


Dropbox Paper: A product that’ll help drive future bottoms up adoption. Also, pages 96-105 of the S-1 are the most fun from a product perspective.

Special Sauce


Bottoms-up consumer delight being a core part of DBX’s DNA

Keyboard Shortcuts: The Blue Bubbles of Apps & Websites

iMessage is a default messaging service on top of SMS on the iPhone where your messages to a sender appear in blue bubbles as long as the other person has an iPhone (yes, even if you don’t sign into your iCloud). If you message a sender who doesn’t have one, DISASTER occursyour messages are now in green and you think of the counterpart differently. This stark call out of bad behavior in iMessage is probably one of the one biggest reasons of why people don’t move off of an iPhone. It forces you to think about the pain that the other person might feel when their message goes out in a green bubble should you make the switch away from an iPhone; making iMessage one of the biggest moats that the device has. The blue bubbles of iMessage helps justify owning an iPhone as it’s probably your most used app.
Similarly, I’ve noticed that when an app or a website has a strong set of keyboard shortcuts, it becomes indispensable once you’ve learned these shortcuts. The app becomes navigable without the need of a mouse, which dramatically increases your productivity on there. The #1 feature you use in the app becomes the keyboard shortcuts and the thought of needing to re-learn them on a different app becomes pretty daunting, preventing you from evaluating alternatives. The keyboard shortcuts become a pretty strong reason to keep using the product. Even though it’s not as strong as the iMessage bond on an iPhone, it’s still a pretty powerful one, especially for power users.

For example, Gmail, the Adobe suite, Paper, and Slack are good examples of products where I cannot live without the keyboard shortcuts.

If you’re building an app or service, it’s probably a great idea to carve out time to make it accessible via keyboard shortcuts. It’ll impact your churn and keep power users very, very happy. 

NYE 2017

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Catching Up Doesn’t Have To Suck

​One of the hardest things for me to do is playing catch up.

This doesn’t refer to something new that I am curious about or want to become good atit’s about catching up on things that I used to be good at or something I have lost momentum on. I have always felt a sufficient drive and enthusiasm in making the time to learn, practice, and execute something new.  It’s been much easier to stay in the mindset of, this isn’t something I want to be good at any more (but not always more on that later). 

This tweet storm titled Some loose thoughts on ego, fear and losers” helped me realize the parallels between my attitude and the Aesop’s fable, The Fox and the Grapes.” Something that seems unattainable has now been termed sour grapes”; hence, it’s unworthy of my time and effort. This is a good rationalization, but it’s a blanket protecting me from my own fears between where I am and my expectation of where I want to be. 

Much of this past week, I have tried to recollect times when I have succumbed to this behavior and why I didn’t go back to the original activity. There have been many reasons:  

  • Inertia: The path of least resistance is to do nothing. Depending on the activity, the amount of activation energy needed to get started again might be variable, but it’s certainly a blocker. 
  • Fear: I used to be good, but if people find out I am not good anymore…disaster.
  • Regret: Imagining how much progress could’ve been made in the time that passed. The present hasn’t lived up to the future you had expected in the past — you regret how time was spent. 
  • Competition: People who I consider my peers are further ahead on some arbitrary scale. They’re ahead and I need to catch up. 
  • Prioritization: This is no longer a priority for me, so I don’t need to go back. Funnily enough, this is a sword that cuts both ways: it’s a weak excuse to not go back or it’s an incredibly powerful tool to eliminate non-critical activities. 

Having become aware of these reasons, I’m working to spend time improving upon my behaviors. Here are a few ways that have helped me over the years to get back into things and make catching up suck less: 

  • 10 Minutes: Start with doing the activity for just 10 minutes and make sure to accomplish something small. This will help build momentum and help evaluate the path forward in a more objective fashion. 

    • Eg. Doing this with writing and publishing it. Just 10 minutes a day has been very helpful in making me comfortable with my own writing again. You’ll be seeing a lot more content here.  Eventually, the activity will last longer than 10 minutes. 
  • Humility: The fear of fear is usually the biggest blocker usually. Be okay asking for help with simple things, and find people you can feel comfortable being vulnerable with and can help you improve. 

    • Eg. Math/Data Science — I am taking an online course to  improve as I haven’t really done any math or Data Science in two years…learning the basics which I was so familiar with is a bit painful, but there isn’t a path forward without it. 
  • Rubric Yourself: Write out goals and milestones that you want to measure yourself against as opposed to comparing against the success/momentum of other people. Be realistic and unrealistic at the same time. 
  • Use Time Gaps as a Tool: Asking yourself to take a break from something you regularly like doing can help evaluate its priority and value. The activities that have I always caught up after a break remind me of my priorities. 

    • Eg. Photography — I didn’t take pictures for most of this year. I recently got my camera back and have made a few hours every weekend getting comfortable with my gear and taking pictures again.

There are 3 activities that I’ve been applying the above to. will have more to share in the coming months on how effective the above has been for me and whether it’s been able to help me making catching up easier. 

Experience of the Week: Wells Fargo Card-Free ATM

A few weeks ago, I saw an interesting billboard by Wells Fargo near one of the first few exit ramps of the freeway after crossing into San Francisco via the Bay Bridge. The billboard illustrated  Wells Fargo’s latest consumer experience/offering – Card Free ATM Access. I was excited because this was one of those product ideas everybody, including me, has probably wondered, “Why it isn’t this a reality yet?” 
I believe the first time this thought crossed my mine  was right after the time I had encountered Venmo in college. I questioned why everything didn’t just work from my phone – the washing machine, the doors, the lights, the vending machine, the ATM, etc. Over the years, lots of startups have been built around this specific thesis. We’ve continued to see mobile become the center of our lives; not just for interactions and transactions online, but more and more, offline too. The latest in the trend towards the latest, surprisingly, has come from Wells Fargo. A legacy bank that is more tech-forward than we imagine. They have  helped in realizing the aspirations of accessing physical money without a card, and I was excited to try it for myself.

I found a WF ATM right next to 16th Street BART and voilá: it works. It takes a few too many taps for it to be a truly magical experience ✨ but it’s still incredibly convenient. This has allowed me to remove my debit card from my wallet and I cannot wait until this becomes a default offering at other big banks as well! 

End Result: 💰💰​💰 without an ATM card! 

What If You Had Bought $AAPL instead of Apple?

I could barely sleep last night so I decided to head to my desk and do a fun project: How much money would you have today if you had purchased the $AAPL stock instead of buying the Apple Product? I do recognize the bias of picking the company that has generated the more shareholder value in the last decade but this is still fun to think about.