Sachin Rekhi

I'm always interested in improving my development stack in order to maximize productivity, facilitate rapid iterations, and maintain flexibility. Over the years I've periodically iterated my web stack, from a Microsoft-based self-hosted environment, to a PHP-centered world, to finally my present Python\Django stack on top of a cloud platform.

I thought I would detail my current stack and technology choices for those interested. I would also love to hear from you on what you use or if you have any suggested improvements.

As many of you know, I spent the last two weeks getting married. Yes, it did indeed take two weeks, including a wedding on April 24th in the Bay Area, as well as a reception in my home town in Rochester, NY on May 1st. Beyond the actual wedding festivities, there were months of planning and preparations prior to the events. Now that all of this has culminated, I thought I would take a moment to reflect on the lessons learned relevant to the startup community from my recent wedding experience.

Based on a suggestion from Andrew Chen, I spent Saturday afternoon reading The Monk and the Riddle by Randy Komisar, which put me in a reflective mood on my own goals and vision for success here in Silicon Valley.

Randy Komisar put together a short narrative that challenges the traditional assumption of the deferred life plan, romanticizes the notion of business as a creative pursuit, and even finds room to go into a discourse on self-knowledge of one's own motivations. Beyond this, Randy litters throughout the book a great set of lessons from his own career as a successful entrepreneurial executive.

I thought I'd take a moment to share some of the highlights through a set of my favorite quotes from the book.

Every week I meet with different entrepreneurs asking for my advice on topics ranging from funding strategy, exit opportunities, user acquisition, monetization, to technology investment. However, unlike others who often have a set of best practices they like to dispense around these topics, I find myself spending a considerable amount of time understanding the entrepreneur's personal goals before laying out my recommendations.

Entrepreneurs come in all shapes and sizes and there are a variety of successful outcomes that can be achieved. It's therefore important to be wary of anyone that gives you one-size-fits-all advice before understanding your needs.

One dimension along which I wanted to elaborate is a founder's choice to optimize for building fundamental vs strategic value. Let's start with some definitions. An entrepreneur that focuses on building fundamental value is optimizing for creating a standalone business that generates meaningful cash flow and profit as an independent entity. On the other hand, an entrepreneur optimizing for strategic value is one that is building their organization in such a way to maximize potential value to a larger organization that will ultimately benefit from an acquisition of the entrepreneur's startup.

Lately I've been spending time thinking about freemium business models and how best to structure them to maximize conversions. I believe we are still early in our understanding of these models and to date most of the available analysis has been limited to anecdotal evidence, one-off case studies, tips & tricks, and a few early overviews of what's been tried.

Despite this I think we are starting to see some interesting emerging design patterns and best practices coming together. I wanted to discuss one such design pattern, including examples of it's usage and potential limitations.

One of the segmentations that is often talked about among Chris Anderson, Eric Ries, etc. is dividing freemium plans into 3 main tiering types: time-limited, capacity-limited, and feature-limited. Canonical examples of each include 30-day trials for 37 Signals' Basecamp, storage space limitations for Dropbox, and mobile access for Remember the Milk, respectively.

One variant of capacity-limited freemium tiering that is particularly effective for products targeted at the SMB market is to scale pricing with customer success. What I mean by this is providing various premium tiers of your product that will become appropriate for your customer as they are more successful in their own business. Typically this means tying the tiers with capacity-limits that either directly reflect or proxy the customer's growth in their own user base or revenue.