Appirio — Lessons from the Untold Stories

In November of 2016, when Appirio announced its acquisition by Wipro, I had the normal range of rollercoaster of emotions you’d expect from a founder. I know all of the founders feel proud of what we accomplished and a large part of that is because of how we got there. We started as a scrappy underdog: we hustled, we irritated industry leaders, we hid behind and even slyly managed our friends at giants like Salesforce. After we grew by riding the tidal wave of cloud fever, we had to confront our own dose of harsh reality — the same tricks didn’t work, growth made us less scrappy, and we still didn’t have the market power of the industry leaders.

Making a company feel special ! Sequoia home page the day of the Appirio acquisition

Never shy to voice an opinion, now that i’m completely unshackled I am using that freedom to reflect on some never told stories of Appirio, and broader lessons I learned from them. I still won’t go full on tabloid. I decided to save stories like “which cloud provider has a terrible technical platform and knows it”, “who has the most unethical sales team”, and “which industry founder was the biggest @$$#!^# defender of private SaaS until he got fired” for nights off the internet…

Nevertheless, there are many stories from the history of Appirio that have never been shared broadly. In them are lessons that could apply to many startups. In this post, I’ve shared ten of the most memorable lessons of Appirio. Hopefully they move beyond many of the normal platitudes you here about success after the fact. They are most relevant to those trying to navigate a trend much bigger than you are (in our case the cloud). In subsequent pieces, I’ll drill into each of the lessons and share some of the more provocative stories of Appirio and the cloud industry we grew up in.

Below are ten of the top, hopefully non-obvious, lessons we learned at Appirio. Follow on posts will stand alone and be linked from here and contain the stories beyond the story.

Before continuing, the one piece of advice you should absolutely listen to? Understand every lesson shared here (and everywhere) could be the exact wrong advice for your circumstance. Universal truths are few and far between and you’ve almost certainly heard them all already. Enough disclaimers, let’s get to it.

1. Taunt the bully — if you have a difference to flaunt — Appirio was known for our constant taunting of Accenture over the years. We were reprimanded by salesforce, cheered by its employees and even once contacted by Tiger Wood’s agent in response. No, we didn’t hate Accenture, we just loved the way the attention drew a contrast between what we were doing and everyone else. [Read the Full Story]

2. Be the pirate and the navy — Steve jobs celebrated Apple as the pirates to the industry’s navy. With two Naval Co-Founders, Appirio took a different tact. With strong discipline, we knew exactly where we stood and the landscape around our business. Even when our actions appeared spontaneous, erratic or even angry, they came from well established principles.We were able to “wing it” on strategy and decisions because we had meticulously planned. We made decisions over a handshake that our competitors took months to even contemplate. [Read the Full Story]

3. Learn from Sun Tzu and High School Musical — You’ll find the Art of War on the bookshelves of many a business leader. Entrepreneurs should supplement it with a dose of insight from High School Musical (or for those of us who remember the eighties: The Breakfast Club, Say Anything, or Can’t Buy Me Love). At Appirio we were too small to outspend our competitors; instead we spent selectively — on lavish parties that fortune 500 CIOs lobbied for invitations to. The power of FOMO isn’t just for high school. [Read the Full Story]

4. Founder’s tales: rediscover the lost art of keeping your mouth shut — With enough time conflict amongst founders is inevitable. Avoiding hard issues and allowing them to fester is nearly always the wrong decision. Gossiping about them freely is equally dangerous. Disputes, issues and disagreements should remain with only with those who are needed to resolve them. Sharing beyond that in the company creates a culture of rumors and an in and out crowd — forcing people in the company to choose sides. Discretion allows you and your co-founders / executives to address your challenges without turning the company into reality television. [Read the Full Story]

5. Growing up is hard to do: face it directly — Early stage startups can be intoxicating. You move fast, have the eyes of the industry on you and grow in leaps and bounds. Yet that growth adds people and eventually you need two things seldom associated with fun — process and management. Face it head on — because losing your culture through this phase is more dangerous than any competitor. [Read the Full Story]

6. Move beyond “kum ba yah” and acknowledge conflict between customers and partners — Your customers may come first, but if your business revolves around partners who are 800lb gorillas there is a conflict of interest. Your reputation with customers’ demands honesty that can’t be compromised. But that runs the risk of antagonizing gorillas. Navigating all of this with honesty requires partner relationships founded on interpersonal relationships between people, not the firms. [Read the Full Story]

7. Treat everyone like they matter, but invest in people like you’re handing them your money — When you first start your company it’s in your own interests to treat everyone at your partners and customers like they are the CEO. It’s important to put ego aside and retain that approach even when you no longer have to. Yet you still must prioritize. Play the long game and invest in relationships not by title but based on who you believe “gets it” and will drive change. If you can’t trust your own judgement on this –inside and outside of your company- you’re probably in the wrong role.

8. Make decisions based on your strategy and self-reflection of who you are — In 2010 Appirio sold our professional services management product (PSA) to Financial Force. They turned it into a success worth magnitudes more than what we gained from the sale. Ultimately, it may help make their company substantially larger than Appirio was. Yet it was still the right decision. We organized Appirio around trying to push the cloud overall. A single app wasn’t consistent with our strategy or culture. Our company had become a next generation services firm and even with our talent, we knew we wouldn’t do as good as job with the PSA app as Financial Force. For them it was a part of their strategy and aligned with their culture. Ultimately the combination must remain in harmony.

9. Success attracts a crowd; evolve or find a new home — Startups are all about convincing the world there is a new or better way to do something. We fight so hard to do that. It’s easy to miss considering how you will react once the world believes you. For Appirio we helped the industry see the vast potential of the cloud. Eventually all the Global SIs sounded a lot like us when they spoke of it. That became our defining problem. Sure, we were nimbler, could execute better and had happier customers — but ultimately we were now on the same playing field. That’s a dangerous place to be with competitors who are 200x your size. Ultimately we were not able to establish a new playing field fast enough — we needed a partner that could help us bulk up so we could win on the one we originally invented.

10. Recognize the privilege — Most startups fail. We all know that. Its why taking a risk to start a company can have such outsized rewards. Yet every day you grow as a company your individual impact is much less than the collective impact of those who decided to join you. They often work just as hard and care about the success of the company and their coworkers just as much as you do. Yet the gains from your collective work will still flow disproportionately to those that took the original risk. I don’t consider that unfair, but do believe it’s critical that entrepreneurs recognize this as a privilege. Too often founders and early executives start to believe their own hype — forgetting all the luck, recognizing but not fully appreciating the contributions of others, celebrating their best decisions without mourning their poor ones, and forgetting the day to day struggles of the people who work at “their company.” Even if living in self serving bubble works, is that who you want to be as a leader?


I’ll take the advice of my last lesson and say thank you to everyone who is a part of the Appirio story. My co-founders, our amazing partners, visionary customers and — most of all — the nearly three thousand people who worked at Appirio over the years. I’m most proud of what you created for one another. I know not every moment was perfect and I’m sure there are those who didn’t have an amazing experience. But I’ve seen first-hand how so many have worked so hard; cared about co-workers and the community; taken an opportunity and turned it into a new direction for their career — and helped those who came after do the same. That spirit of wanting to make things better for each other, our customers, the industry and those who aren’t as fortunate is something I will always remember and cherish. Thank you.


Being a part of Appirio was a life changing experience. I’m hoping my next chapter can take that good fortune and experience to help change medicine and healthcare with technology. Since I ignored that industry for the first twenty years of my career you’ll find me trying to catch up with an amazing group of people (many half my age!) at UCSF and Berkeley in the Masters of Translational Medicine program.