Why Tim Cook is Steve Ballmer

What happens to a company when a visionary CEO is gone? Most often, innovation dies and the company coasts for years on momentum and its brand. Rarely does it regain its former glory. Here’s why.

Editor’s Note: for more on this theme, read “Visionary, Salesman and Pragmatist Model of Business Succes.”

Start-Ups: Stop Wasting Your Marketing Budget

Having the best product won’t help your start-up without a focus on segmentation, targeting and positioning.

The Most Common Mistakes Made By Startups Throughout The Hiring Process

In the venture capital industry, we talk a lot about the importance of the founding team. But we might underestimate, especially in the early stages, something that might be as important as their drive, soft skills and strategic sophistication: their ability to recruit an A-class team. So I wondered, what are the best practices out there? I knew that I couldn’t find the golden formula, … [ Read more ]

How to Calculate Your Total Addressable Market and Make a Great TAM Slide for Investors

I’ve seen hundreds of startup pitch decks and have found total addressable market (TAM) slides to be among the most frequently mis-executed. I get the sense they are often included as a formality in an attempt to get VCs to check a mental box and continue on hearing about other important things: the product, the team, the progress, the go-to-market, etc.
In this piece, I’m going … [ Read more ]

What Seven Years at Airbnb Taught Me About Building a Company

I first joined Airbnb as an engineer, and then as one of the first members of the budding PM team. Back then there were a couple dozen engineers, a few designers, and two very cute dogs. Over the next seven years as the company scaled to thousands of global employees, countless cute dogs, and over $30b in value, I took on a lot of interesting … [ Read more ]

Future Founders, Here’s How to Spot and Build in Nonobvious Markets

For Elad Gil, an important lesson for aspiring founders and investors alike is that nonobvious markets can lead to hypergrowth, but they’re hard to spot in the moment. The trick lies in finding what bucks conventional wisdom before anyone else and scaling that unlikely idea into a high-growth company — something Gil is very familiar with.

In his roles as an operator and angel investor, Gil … [ Read more ]

6 Ways Great Companies Use Board Decks to Their Advantage

After graduating from college in June, I had the chance to spend three months at Union Square Ventures, helping with a project that created anonymous aggregate insights for USV portfolio companies by analyzing data across stages, customers, and industries. In order to not put a lot of extra reporting effort on our companies, we approached this project by drawing from data in existing board decks. … [ Read more ]


Maybe, just maybe, you too have a nagging, gagging sense that the current atmosphere of disrupt-o-mania isn’t the only air a startup can breathe. That perhaps this zeal for disruption is not only crowding out other motives for doing a startup, but also can be downright poisonous for everyone here and the rest of the world.

How to Pitch Your Startup to a Venture Capitalist

Jenny Lefcourt is general partner at Freestyle Capital, a venture capital firm that specializes in seed and early-stage investments. She knows what it takes to be an entrepreneur because she’s been there. Lefcourt co-founded two companies — WeddingChannel.com and Bella Pictures — after dropping out of Stanford Business School. Meetings with investors to pitch the business and raise capital left her with a deeper understanding … [ Read more ]

The Imperative Practice of Relaxing Constraints

Howard Morgan is an encyclopedia of tech history and startup lessons. And all that he hasn’t experienced firsthand, he soaks up, too. (He keeps a running list of all the books he’s read over the last 30 years; it’s over 5,700 entries long.) In this exclusive interview, we dig into the practice Morgan has seen differentiate good founders from great founders: the ability to relax … [ Read more ]

What Do I Look for in a Pitch?

Founders will often ask me, “Do you want to go through our deck?”
It’s not about the slide deck. We have made the decision to invest in entrepreneurs without slides, whose ambition, passion, depth of understanding of an opportunity and compelling vision come through crystal-clear in conversation.
But…that’s a high bar for communication. Most of the time, putting a business plan on paper helps you structure a … [ Read more ]

Founder Dilution

In my experience, it will generally take three to four rounds of equity capital to finance the business and 20-25% of the company to recruit and retain a management team. That will typically leave the founder/founder team with 10-20% of the business when it’s all said and done.

7 Lessons From 100+ Failed Startups

There’s a joke about startups. “For every 10 startups you see in the market, 11 of them will fail.” I didn’t want to think that my startup would be the one to fail, and no entrepreneur does. I thought I knew it all…or at least would learn it all during the process of launching my startup. After my own failure, I became obsessed with understanding … [ Read more ]

Something Weird Happens to Companies When They Hit 150 People

The dynamics of companies change fundamentally when they exceed roughly 150 people, in ways that startup founders can struggle to address.

Hypergrowth and The Law of Startup Physics

Khalid Halim notices patterns in startups that how companies scale and break matches military groupings. In this exclusive interview, he pulls at the strings of this scaling-and-breaking phenomenon to articulate what he calls the law of startup physics. He explains how companies and people grow at different rates — and what this tension means for how both will break while scaling. Halim shares how he’s … [ Read more ]

The Cognitive Distortions of Founders

Cognitive behavior theory says automatic thoughts color and distort our observations, our judgments, and our actions. These automatic thoughts come to mind without even trying. They reflect deep beliefs about self, past experiences, and expectations for the future, and they have a profound impact on judgment and behavior. I’ve met thousands of founders over the last decade or so and I think many of them … [ Read more ]

Startup Pitch Decks

In my short career as a VC, I’ve reviewed thousands of pitch decks and helped hundreds of founders refine their pitches. Additionally, I’m often approached by founder friends to provide feedback on their slides before they go to market. Given pitch decks are frequently discussed and they’re essential in the fundraising process, I thought it would be useful to create a simple guide to building … [ Read more ]

Assembling an Executive Leadership Team is Daunting — Let Thumbtack’s CEO Help

For the first-time and early-stage founder out there, it can be daunting to recruit and hire executives — especially when you don’t have enough knowledge to test them for skill in their area of expertise. In this exclusive interview, Marco Zappacosta shares his four-step process for identifying and vetting his leadership team. From job descriptions to interview questions to references, Zappacosta shares his approach to … [ Read more ]