This is Matthew

The Value of Capital Constraints

Quibi is shutting down, and everyone has an opinion. While the Quibi debacle inspires this particular post, it isn't about Quibi. It's about the value of capital constraints. When you start a venture-backed company, you want to raise more money. Whatever amount of capital that you wish to raise, you

Mandatory & Preferential Voting

In 2002 I spent a semester studying abroad in Adelaide, Australia. One of the classes I took at the University of Adelaide was an Introduction to Australian Politics. I enjoyed the course thoroughly; it led to me understanding the parliamentary system. One aspect of Australian politics that stood out to

Information Asymmetry in Startups

We all know that having information and insights can allow you to make better business decisions. It can help you close deals, avoid time-wasting activities, and accelerate your business. I've noticed a particular information asymmetry in startups around what startup founders know about investors and what investors know about startups.

Remembering the Digital Divide

I've recently been in a lot of conversations about how school is going this fall. My children are starting their sixth week of virtual school for the year, and I don't expect them to return to in-person learning any time soon. I prefer to stay positive and optimistic and tend

management

Talking About Why People Are Leaving

This post is a post I can only write because it has been a long time since I've had to let someone go from a role (and when it should be along time when I need to do so again). It's not about anyone in particular. People, all of us,

Entrepreneuship

Building and Selling

I've taken an extended hiatus from blogging. We all know 2020 threw a lot of plans to the wayside. The loss of routine has undoubtedly had an impact on my writing. The web site littered with blog posts saying people will write more frequently with no follow-up, but I will

More on the Death of Expertise

I've spent a lot of time thinking about the death of expertise. I wrote about it two years on this blog, but it feels like something that comes up frequently. It is once again at the time of my mind during the COVID-19 pandemic we are all experiencing. To me,

My Latest: Grand Reserve Rewards

Today, we launched the first product from my new company, Vertical Finance. Many people have asked what we've been working on and it's a real pleasure to share it with you now. Reposting our welcome letter from Grand Reserve below: The idea for Grand Reserve came to me several years

Founders, Initial Employees, and Risk

A recent discussion online and several real-life conversations have had me considering the risks and rewards of founding startups as compared to being an early employee. Most of the conversation focuses on the financial risks and rewards of whether or not it is worthwhile to be an early startup employee.

Not So Easy

Today I heard a statement that I am hearing frequently: "It's easier than ever to start a business." This statement is usually followed by some discussion of how great Amazon Web Services is or the cloud in general. The concept is that instead of spending lots of money buying servers

The New Stakeholders

Business Roundtable Redefines the Purpose of a Corporation to Promote ‘An Economy That Serves All Americans’This announcement by leading CEOs has certainly been a hot topic as of late. I have been asked my opinion a few times. If you haven't been following along, the issue at hand is

Arrogance and Humility

Leadership requires being visible. We can discuss leading from in front versus leading from behind. We can also discuss leadership versus authority and many other interesting ways to discuss leadership. Through it all, however, I believe there is a requirement that as a leader you are visible. You have to

Office Space

Ever since I've been in the professional workspace the open office design is all that I have known. For years now we have had research that shows that the open office is a trap. As I think about how to build my next company the question of how to build

Product Management

Reasons to Buy, Reasons to Believe

When attempting to define a product, it is key to discover the core value proposition to the user or customer of the product. For many products, this results in the product developer putting together a long list of benefits and values. Here's the problem: defining what is core. It is

Startups and Heads of Product

As I've taken the past few months off, I have been having a lot of conversations with startup CEOs about product and product management roles. Some of this has been in the potential discussion of my joining their teams and some of which has been in more general advice. Over

Startups

The Bias of Success

I've noted previously that 0.2% of startups have a chance of having an IPO of more than $1 billion (very different from companies that at some point were valued at more than $1 billion). Naturally, when there are articles and advice on how to be successful it is from

Product Management

What is your user's problem?

For product managers, the most important part of the job is truly understand what the user's problem is. It sounds easy, but in reality, understanding and defining a problem clearly is a huge challenge. Product managers need to identify problems and prioritize those problems. This enables a product manager, in

Startups

Decision-Making Speed in Startups

Startups are constrained by many factors. These include financial capital, team size, and speed. The ability to hire great people is constrained by both competition and by financial capital. The ability to raise financial capital can be constrained by market conditions and experience with fundraising. Speed, specifically, decision-making speed, is

Startups

Startups and the Death of Expertise

There are many startup-related myths out there. These myths occur when the rare and exceptional events become assumed to be the mundane and normal. This is to be expected; if an event were mundane it would not be reported in the media or shared among people. Mundane events are ignored.

Startups

Obligatory Why I Left My Job Post (Second Edition)

More than six years ago, I penned my first Obligatory Why I Left My Job to Start a Blog Post. It was short and a bit confusing, upon reading it again now. Last month I left Red Ventures, which had acquired Bankrate, which had acquired Wallaby Financial, which is the

Perils and Powers of Pride

Pride makes most of us do stupid things. I don't know the true origin of the quote, but in the context of the current discussion around harassment and assault someone said that women are afraid men will rape and kill them, while men are afraid that women will laugh at

Unintended Consequences

I tend to believe that some government regulation is a good thing overall. Especially in today's economic situation, where fewer large companies dominate that landscape, and learning from the 2008 financial crisis, I believe there is value in the government setting reasonable guardrails. Coming out of the Dodd-Frank Act is

Levels and Title

Most startups want you to believe that they have a fundamentally unique culture. This makes each company special. The reality is that most startups subscribe to the same types of standard cultural norms for the workplace. They are just trying to sell you on it so that you will work

Announcing Departures

Over the past few months there have been quite a few departures at my place of work. It's a combination of things. Some people have been terminated, some people have left for other jobs (or no job), some people were laid-off when the company was acquired. I've received a lot

Year End Reviews

Year end reviews are usually terrible. It's a long complicated form from Human Resources that seems designed to be a complete CYA move. My last form had "demonstrates ethical behavior" on a scale of 1 to 10. I mean come on, can you be only partially unethical? I'd