The ToutApp Story

As ToutApp has grown over the past few years, I’ve been diligent about writing out my lessons learned, yearly reflections and core principles. This has amounted to nearly 83+ posts (as of August 2014). On this page, I’ve tried to outline some of my best posts for those that are interested in seeing what it takes to start a business from scratch and grow it over time.

Yearly Reflections

One of the things I always made a point of doing was to write my own reflections at the end of each year of running the business. Not only did it help me understand where we started and where we ended up, it also helped me distill and clarify my own thoughts on what “moved the needle” in terms of the business.

2010 – I quit my job. Shipped 2 products. Launched a Services business with clients. Now what!?

2011 – A Year in Review, 2011 Reflections in 2011, I talk through how I decided to focus on Tout as a real company, raise our first round and build a team

2012 – Reflecting on 3 years as a Startup Founder, In 2012, I talk about how we figured out our target market, rebuilt our team, and increased revenues

2013 – It takes 3 years, In 2013, I talked about what happens to a SaaS business once you’ve managed to survive for 3 years and how a ton of things start to come together

2014 & 20154-key lessons learned about being CEO of a SaaS Business Through 2014 and 2015, I switched to being a true CEO of a venture backed company as we raised our Series A and Series B. Here are my reflections from those two critical years and lessons learned.

The Art of the Start

One of the hardest things about Startups is actually starting. There are those that raise millions up front, get on Techcrunch, and do a massive launch, only to fail. There are those that go through meticulous Excel analysis to define a target market, problem and solution and then never start due to analysis paralysis. And then there are those that set out to solve a simple problem and stumble upon a goldmine and go on to build a real company.

For me, I’ve been through a lot of different permutations of the start, but the one that ended up working was when I just solved a problem myself, and luckily stumbled upon a market that was dying for a solution to a massive problem.

If you’re looking to start a startup, you should read these articles that outline the days leading up to and the early days of starting ToutApp.

How I made a Principled decision to quit my Six Figure job

My 1-page Wireframe of ToutApp

How My Weekend Project Turned into a Real Lean Startup

How I Set Out to Kill Email and Ended Up Making It Better

10 Things an Entrepreneur Needs to Get Started — The Entrepreneur’s Starter Kit


When you think about building a startup, inevitably the topic of funding, fundraising, angels and VCs come up. As we ‘ve gone through our advisory round, our seed round and even our venture backed rounds, I’ve blogged about some aspects (but not as much as I’d like to have) of the journey. If you’re fundraising, these posts may be valuable.

Why I’m switching from being a bootstrapper to a funded startup

ToutApp raises $350k from Esther Dyson, Dave McClure, Eric Ries, and Others

How I Raised $350k as a Solo Founder using these 4 Email Templates

Reflecting on my Summer at 500Startups

There are more posts I plan on writing about our Seed round, our Series A and on-wards. If this is something that you’d be interested in, email me and let me know so I know people want it!

Keeping On

If there is one thing I’ve learned from ToutApp, it is that building a company, a real company, takes time, patience, and grit. I didn’t learn this in one fell swoop, and at a high level this sounds obvious. What I did learn is that going the distance requires you to manage your head game. Here are the different strategies I discovered, developed and implemented to keep my head game straight as a Startup Founder and as a CEO:

Heads Down Mode

Bumbling and Awareness During Heads Down Mode

Jab, Punch, Jab — the Startup Mantra

Rule #1 – Show Up

How I Gained More Confidence as an Entrepreneur

Take It Easy

Core Principles

As I built ToutApp over the years, and as I continue to do so, we always tried to tackle new challenges in a first-principles basis. As we set out to define principles that we believed in, I wrote some of them down on this blog so that others could benefit. Here are some of the most pertinent ones.

9 Principles Behind an Effective Landing Page

Principles Behind a Freemium Pricing Model

Principles Behind Customer Service at a Startup

How to Interview an Engineer for your Startup