Artificial Intelligence is Exposing Laziness

We're all secretly (or perhaps not so secretly) freaking out about the pending AI job apocalypse. There is more to write about on that subject, but I want to focus on something I have noticed lately as Artificial Intelligence (AI) adoption grows: the exposure of people who try

Are We All Developers Now?

I can't seem to resist weighing in on the conversation about vibe coding. The great gold rush of app building is here (again), reminding me of when mobile apps for iPhone and Android first appeared. The App Store debuted in 2008 with just a handful of apps, including

Can You Introduce Me to Investors?

I am frequently asked this question by early-stage founders I meet. While there are many other posts online about idealized ways to do this, I want to write my own post to share with people when they ask me this question. I'll include a resource you can copy

Hiring for Attitude, Coaching for Aptitude

I was reading a long story in The Athletic about how NFL teams fail their high-profile first-round quarterbacks, and it got me thinking about hiring tactics and coaching again. The part that stood out to me was a comparison of how scouts and coaches view prospects: Hasselbeck cites a disconnect

So You Sold Your Company, Please Let Me Know

Today's post is going to be a bit of a complaint. It is the natural progression of a business that if you start one and seek outside investors, those investors will want a return. As a result, you will need to sell the business. Added to this challenge

Founders and Fraud

I was reading the news when I came across the story of Christine Hunsicker, who was charged in a $300MM investment fraud scheme as part of her startup, CaaStle. I don't know anything about her or her company, but this is yet another example of investment fraud in

Priorities, Focus, and the Eisenhower Matrix

It’s very easy to get distracted. I’d argue it’s easier than ever before; thanks to modern technology, we always carry at least one screen with us, often two or three. Distraction is also more common in remote work settings. In an in-person meeting, you’re less likely

Talking to Users

A lot of ink has been spilled on the topic of talking to your users. Product leaders and entrepreneurs write about it with good reason: If you don't talk to your users, you don't know how to solve their problems. Founders have two starting points: 1.

Try to Stay Calm

Calm the Fuck Down: A Founder’s Guide to Surviving Startups I’ve long wanted to write a book about startups. The working title? Calm the Fuck Down. It’s a mantra that I’ve needed to remind myself of repeatedly over the years, especially during the Wallaby days, and

Cerro Grande & Eaton Canyon

This past Tuesday, January 7, a fire of unknown origin started in Eaton Canyon, a gateway to the Angeles National Forest at the eastern edge of my current hometown, Pasadena, CA. The fire exploded out of control, and while the damage assessment is ongoing, I am sure 10% or more

Startups

To Whom Should You Pitch?

Founders often ask me to introduce them to venture capitalist investors (VCs) that I know. My first question is always, “Which VCs do you want to meet?” Many folks don’t have an answer. I’m not asking to be difficult or to throw them off, but because not every

Startups

How I launched my company with no co-founder, no money, and no hope of survival

Recently, I have had a lot of conversations with founders about the value of public relations. Folks, generally speaking, don't want to spend money on it because it isn't clearly measurable marketing. In contrast, when you spend money on Google or Facebook ads, you know how

My Second Favorite Type of VC

A joke: Q: What's your favorite type of VC? A: Ones that say "yes." An insightful answer: Q: What's your second favorite type of VC? A: Ones that say "no." I am enjoying operating a business without outside investors (nor plans to

Not On Substack

Earlier this month, The Atlantic reported that "Substack has a Nazi Problem." On December 21st, co-founder Hamish McKenzie published a note on his platform with a clear answer: I just want to make it clear that we don’t like Nazis either—we wish no-one held those views.

New Adventures

It's been far too long since I wrote anything for my blog. Much of my writing efforts have gone into my substack, CardsFTW. My busy work life has also sapped much of my energy for writing here. It's once again time for a blog post about

Startups

Taking Off Hats

At a startup, everyone needs to wear a lot of metaphorical hats. With a small team, each person can have many responsibilities. Most companies have a pair of co-founders, one technical and one business-focused, on day zero. The CTO often must act as a product manager, engineer, technology operations, and

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

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

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

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.

entrepreneurship

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

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.

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

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.