Photo Cred: Ulises Baga

What if I told you that you could have a healthy and trusting co-founder relationship? What if I told you that you could meet any roadblock head-on? What if I told you there were simple practices to create a stronger union with your co-founder? Here’s the good news: this is all possible.

I’ve been working with co-founders as an investor and coach for a decade, and while I’ve helped many co-founders improve their communication and deepen trust, I’ve witnessed countless co-founder splits. This includes numerous clients, friends, and even my wife. I’ve seen close friends, college roommates, and former colleagues…


2020 has stretched us, unlike any year in history. All of our lives have been upended. We’ve had to cope with COVID-19, social distancing, work from home, the election, economic hardships, and much more. This year has been truly unprecedented.

Thankfully, it’s time to turn the page on 2020 and begin to look forward to 2021.

I’ve always believed December is the perfect time to step back and reflect on what we’ve experienced and learned over the past twelve months. It’s also an ideal time to define what you hope to accomplish and change in the year ahead.

Dating back…


(this was originally posted on my blog at schlaf.me)

Since I started coaching three years ago, I’ve supported countless founders who have experienced some form of deep and/or prolonged rejection. This includes being passed on by superstar recruits, having an M&A deal fall through at the eleventh hour, and hearing “no” from a hundred VCs.

Here’s the reality: rejection is part of the entrepreneurial journey. Every founder experiences it at some point.

Rejection is defined as dismissing or refusing a proposal, idea, etc. It describes a person or entity pushing something or someone away or out. According to Mark Leary


(This post was originally published on my blog at schlaf.me)

I recently had an exchange with James Beshara, Founder of Magic Mind and creator of Below The Line Podcast, about having a multi-path career.

Embarking on a multi-path career has been a big adjustment for me. Not even a year ago, I had a single career as an institutional investor. This was my life and identity for nearly a decade. The transition from VC to coach, angel and creator has been incredibly life-expanding but also challenging.

Each month, I spend countless hours collaborating with dozens of founders, executives, and creators…


(This post was originally published on my personal site at schlaf.me)

At about 6:15 this morning, I completed another rotation around the sun and turned forty-one. Even though I’m relatively young and healthy, typing this number makes me more reflective because I’ve officially landed in midlife.

Despite COVID and the state of the world, the past year has been the most fulfilling, productive and expansive of my life. I transitioned from being an institutional VC to a coach. I moved from NYC to the Catskills. These were just two of the many events that shaped my life.

In the days…


(This was originally published on my personal site at schlaf.me)

Last weekend, Dom Holland, the outspoken and inspirational CEO of Fast, shared the following tweet:

I don’t know Domm or his intention behind his tweet, but I couldn’t disagree more with the basic message. This is generally bad advice and doesn’t send the right message to the scores of founders who follow him. It’s also a privileged perspective. There are millions of humans who need mentors far more than either Domm or I can even comprehend.

We shouldn’t be shouting from the rooftops saying, “You don’t need a mentor.” Instead…


Photo: Tim Mossholder

I wrote this post four years ago but didn’t publish it for a variety of reasons. Every word written below remains untouched and unedited all these years later. As I celebrate my fifth anniversary today, I thought it would be a fitting milestone to finally share my initial road to recovery. Sobriety isn’t something I’m ashamed of. In fact, it’s a superpower. I wouldn’t be who I am today if I didn’t go on this journey. May this post inspire you to discover the superpowers that are already deep inside of you.

June 5th, 2016

“Our lives begin to end the day we…


Photo: Alice Donovan-Rouse

Authors note: I co-authored this post with Romeen Sheth, President of Metasys. It originally was published in TechCrunch.

“Peacetime CEO/Wartime CEO” by Ben Horowitz is one of the most commonly cited management think pieces of the last decade. And for good reason. Horowitz has surfaced a fundamental distinction in operating philosophy that is necessary for companies to survive, reinvent and ultimately win when macroeconomic environments shift. …


Last fall, I made the decision to leave institutional venture capital to coach startup leaders and angel invest. While I’ve enjoyed being an ‘Army of One’ for the last six months, I’d love some help and support as we head into the summer.

I’m now kicking off a process to hire my very first intern to help me with a variety projects and processes related to my angel fund and High Output, my boutique leadership development company. This lucky person will be my right hand for the summer. …


Photo: Vegan Liftz

Since I’ve been in quarantine, I’ve been hooked on my devices. In fact, it feels like my iPhone has become an extra appendage. It follows me wherever I go, even in bed sadly. Despite my best efforts at times, I’m addicted. That’s not an exaggeration.

Late last week, it occurred to me that I was spending the majority of my time in social feeds, email and text. I was incessantly scrolling and staring at screens hour by hour, day after day. Not only has my attention been hijacked but also hours of my time have seemingly vanished. …

Steve Schlafman

Founder & Coach at High Output. Angel Investor. I help the creators of tomorrow realize their potential as humans and leaders.

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