My First Big Sales Deal
In my first start-up, I was mostly hunting whales — seven figure and eight figure deals. I had no experience doing any of this. For our First Big Customer, we’d been negotiating a $6m/year contract for quite some time (they always take time). We finally had the “all hands” meeting with all the C-level and […]
Dharmesh Shah of Hubspot: From Day 0 to IPO. What Went to Plan. What Most Certainly Didn’t (Video + Transcript)
In anticipation of the upcoming SaaStr Annual 2017, we’ll be releasing the full series of transcripts and videos from all the awesome 2016 sessions. There are rules in starting an enterprise software company. You will fail if you: 1) try to build a suite of products out of the gate, 2) focus solely on SMBs, or 3) […]
Why Some SaaS Companies Stall Out at $20m ARR
Part of my job when I invest in a start-up is to get folks excited about the company. It’s not that hard. Because I am genuinely excited. Or I wouldn’t make the investment . And part of the picture I try to paint for the The Next Investor is where they’ll be in 12-18 months. E.g., […]
Why We Can’t Let Luddites Ruin Global Trade
Luddites. It’s a term most of you know as being somebody who is backward or uninterested in learning new technology. Actually, the Luddites were worse than this. They were a movement in England during the Industrial Revolution who had the objective of ruining machinery that was used to build products at scale. They thought […]
Why Raising Too Much Money Can Harm Your Startup
Amongst the most often asked questions I get from founders is, “How much money should I raise?” Reflexively founders want to raise as much money as they can because they figure it will give them more resources, better chances of competing and a longer runways before they have to do the often painful job […]
Why Acceptance of Failure is Critical to Startup Success
I talk about failure a lot because I think it can be tremendously instructive and I think that success without failure often masks underlying lessons. I even prefer to fund entrepreneurs who have experience some level of set-backs in their careers or startups because I think it brings a humility to decision-making that I […]
The Corrosive Nature of Over-Introducers
In modern society we’re all over-worked and over-loaded with information and tasks and to-dos and obligations. Nowhere is this more apparent than working in a startup where you are definitionally under-resourced and trying to make big accomplishments in compressed periods of time. That’s why focus is critical. Saying “no” often to people who want […]
Small Deals at Large Companies. Hooray!! And 100% At Risk.
Every customer you close, the next day, is at risk of churn. A month-to-month customer can basically cancel anytime. An annual contract customer can sort of cancel anytime, but really probably won’t for a year, or even 3 (more on why Year 3 is the biggest risk for bigger customers here). You know this, of […]
e-Staff Meetings and 1-on-1s: You Gotta Do Them
For the first time in my career, I’ve worked with amazing first-time managers as CEOs. Before I was a CEO, I was a mid-level manager, a director. And then a VP. Across a few start-ups. Before I was first a founder. Those management team weren’t perfect, and I wouldn’t copy everything they did. But at […]
4 Tips To Earn Respect as a Young CEO
While age ultimately doesn’t matter — results do — in SaaS, starting off as younger-than-average can create stress in a sales and customer-driven environment. But Aaron Levie started Box at 19, Mark Zuckerberg and Bill Gates dropped out at 19-ish, you know all this. Some some hacks: Start with SMBs. It’s easier to get taken seriously, […]
Disconnect To Reconnect
All journeys, no matter how fruitful, come to an end. After a little over nine and half years I decided to leave SAP last week. What a journey this has been! Making Design Thinking real I was hired into a multidisciplinary corporate strategy team, set up by Hasso Plattner, the chairman of SAP’s supervisory board, […]
CIO workshop: ROI of customer experience
Customer experience is one of those vague phrases that one hears about digital transformation (itself one of the most common jargon buzzwords of our time). There are two issues associated with customer experience: determining the meaning and quantifying the value or ROI. To understand the meaning, let’s turn to two authoritative sources, Dion Hinchcliffe and […]
Why The LinkedIn Acquisition is So Important to SaaS
So, Microsoft bought LinkedIn for $25.6 billion dollars. That headline shocked all of us the other day. But if you step back, it’s not that impressive, the raw number itself. After all, as a public company, LinkedIn was worth $32 billion just a few months earlier, and had been on one heck of a run […]
The Easiest Ways to Get From $1M ARR to $10M ARR
The most important thing is not to chase the shiny penny, assuming you are growing at least 60% Year-over-Year. You’ve done the Impossible. You’ve gotten 50, 100, whatever # of businesses to pay you $1,000,000 a year. There are 10,000 new apps out there. It’s “impossible” to get to $1m. You did it. Now, the […]
How to Avoid Being Replaced as CEO by Your VCs
Worried about a bunch of VCs replacing you? You should be a little worried, probably. Just the other day, a CEO that I know fairly well was fired by a VC. Strange thing was, the VC didn’t talk to the rest of the board. Who didn’t agree. So he got un-fired. Awk. Ward. CEOs getting […]
