We’re good at setting goals. Reading reports. Providing updates. Solving problems. We’re terribly efficient in Covid times. We wake up, affix our eyes to screens and barely budge for hours on end. We review roadmaps, project plans, and dashboards. We attend and run meetings with discipline. We’re machines.

And everywhere I look I see teams fraying at the seams. Great cultures degrading. Loyal employees spiritless. Once passionate team members with sunken eyes and suffering souls.

There are no team lunches. No serendipitous encounters at the coffee station. No happy hours, birthday parties, or off-sites. No walking into the office together…


And How to Vet Them Appropriately

Image by Javier Allegue Barros via Unsplash.com

A productive board of directors is a beautiful thing. It’s an accelerant. The group amplifies a leadership team’s thinking and extends its reach. Great boards open doors, challenge strategy, provide wisdom, and entice talent.

I’ve participated in a lot of startup board meetings — as an officer, director, and observer. I currently sit proudly on two boards (Worklete and Teampay.co) And thanks to the Enjoy The Work portfolio, my partners and I are exposed to dozens more.

Not all boards are well functioning. When speaking to our founders in such situations, we show balance in our guidance. We know we’re…


I was asked by a founder this week looking for support, “Any chance you guys have guidance to companies on an optimal black lives matter response?”

Short answer. We don’t. Not even close.

I don’t even know what optimal in this circumstance means. What is the optimal response to racism laid bare? What is the optimal response to a public assasination? What is the optimal response to what feels like a system of injustice impenetrable to protests of every form and elections of every era.

I’m numb. I don’t want to feel this way. But I do. It’s how my…


I keep seeing the same mistake.

A founder with a worthy idea brings a new technology into the world. The early generation of the technology wins some early customers, which leads to first revenue, which leads to first capital. The company begins to grow.

The company is well run with milestones, a financial plan, clear goals, timely communications, and regular dashboards. There is a rhythm. For every department, there is clear accountability… except one.

The product team is always late. And no one really seems to know why.

We know the leads we need to generate, the sales we need…


There is no correct reaction. You only can under react or overreact. And you won’t know which path you’ve chosen until the event is behind you.

We work with founders of every type. We have founders who are technically inclined. We have others who come from finance, marketing, or sales. We have first time founders and still others who are veteran entrepreneurs. We have startups worth hundreds of millions of dollars and others freshly out of accelerators.

Yet all founders are asking the same questions right now:

  • How will this pandemic and the developing economic shock impact my sales?
  • How…


Founders often have good sales instincts. They can read the room. They can tell a solid story. It’s not always polished or entertaining, but authenticity and passion more than compensate. It works great for one-on-one interactions. Need to convince one person? Recruit one candidate? Court one investor? Most founders are up to the task.

But what happens when a deal is not one-on-one? What if it’s one to many? What if it is highly complex with lines of authority, budget calendars, unclear politics, a procurement department, an RFP process, technology diligence, and/or a legal review? …


Have you ever sat in a meeting and wondered halfway through what the hell people were talking about? Or have you suffered seemingly bottomless email threads so long you struggled remembering why they started in the first place?

Every one of these moments brings cost. That cost is as real as buying equipment, acquiring media, or paying a legal bill. Founders understand that inefficient execution costs time, and time is not free. So why does it happen anyway?

I obsess about hidden costs.

They’re sinister in their invisibility, staying clear of detection and therefore, elimination. It’s their subtlety that makes…


Imagine perfect information flow at a startup…

The CEO articulates why the business must exist in the world. The leadership team and the entire workforce (via a Neuralink connection of course) fully understand the vision. There is no data loss or confusion as the story spreads from person to person.

The leadership team translates the vision into a series of initial target outcomes, the realization of which would indicate that the team is on the right path. The wider team fully comprehends the desired near-term outcomes and builds perfectly aligned action plans and accompanying leading indicator reports. The “why,” the…


Thirteen lovely people attended the first ever Enjoy The Work social. We occupied a single table at Chez Maman in Potrero Hill in San Francisco. We introduced ourselves, told some stories, ate good food, enjoyed fine wine, and most importantly, nourished new relationships. Special thanks to Eric Dy and Julien Penders of BloomLife, Kate Blake of 6x Project, and Nick Kohut and Andrew Gillies of Dash Robotics who are as much members of our community today as they were back then.

That was January 14th, 2016. Nearly 4 years ago.

At ETW, we often talk about serving those founders who…


Early stage fundraising takes a toll. A successful raise often requires months of preparation, pitching, and negotiating. You must craft a story, answer questions, prepare materials, and defend a financial plan. Then you get the pleasure of repeating yourself endlessly, often to investors only casually curious about your life’s mission.

It’s exhausting — and worse, it often ends in failure.

But for the fortunate minority who do raise the capital they desire, another danger lurks. It’s the honeymoon period.

I’ve seen it many times. Over the past 3 years, we’ve guided more than 100 fundraises. A distinct pattern exists:

Month…

Jonathan Lowenhar

President of @EnjoyTheWork. Startups, laughs, wisdom and irreverence (order unclear).

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