Startups - This is Matthew

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

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

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

Startups

Five Things About Fundraising

I've been asked a lot about my fundraising experience. With the latest e-mail, I figured a blog post would be a productive answer, by making it available to all. In no particular order, here are five quick thoughts about fundraising I usually share: One. Self-Confidence No one will, nor should

Startups

How to stay semi-independent after selling your startup

Note: Venture Beat first published this piece of mine. Last December, my cofounder Todd Zino and I sold our startup, Wallaby Financial, to Bankrate. We immediately went from being a team of nine, on the verge of going big or going broke, to being part of a 600-person company valued

Startups

The Negative Side of Negative Advertising

As a startup, you are engaged in a competitive battle for investments, customers, revenues, employees, and more. You have to decide how to go to the competition and what tactics you will use. Negative is not a good answer. With the launch of Apple’s latest iPhone 6/6 Plus,

Startups

Vote for my SXSW Panel: "Regulated: Startups That Have to Follow the Rules"

Software is eating the world. Startups are fighting decades old laws to build new business models that are more efficient, serve users needs, and grow profitably. Regulated industries remain a huge open space of opportunities, if you can stomach disrupting and following the rules at the same time. Four successful

Startups

Disrupting the Male-Dominated Startup Culture

There is probably no way that this post comes off well, but I’m going to try it anyway. Credit first to the anonymous author of What It’s Like Raising Money As A Woman In Silicon Valley that was published in Forbes yesterday for inspiration. First, let’s establish

Startups

Why My Team Doesn't Look Great on Paper

Left, Ashvin, CEO of Themer. Right, Me. Claremont McKenna Graduation, May 16th, 2004. There is a really interesting article today in TechCrunch today about credentials and Silicon Valley. Great work by Danny Crichton that hits it right on the nose that Silicon Valley loudly proclaims its qualities as a meritocracy,

Startups

Why I Started Wallaby

About one-and-a-half months ago, I wrote a blog post entitled “Don’t Start a Company to Be Your Own Boss” It had better coverage than I expected, gaining some noticed on HackerNews. Because that post focussed on a reason not to start a company, a couple of

Startups

Reckless Startup Spending

When a startup is having trouble its spending is reckless (see BeachMint article at Pando). When it’s doing well, that same spending is fun and culture building. Nobody knows for sure the right path. I think Google’s continued belief that they should buy everyone breakfast, lunch and dinner

Startups

How To Land an Internship at a Start-up

TL;DR Like any other job, do your homework and choose carefully At Wallaby Financial, we like to have a product management intern on hand at all times. First, it’s a great source of inexpensive labor (more on why we pay in a later post). Second, we like to