October 5, 2023
Finding Professional Purpose
...and what I'm now building with Upside
Archive
Posts
All posts live at /posts/[slug], ready for the rest of the site to grow around them.
September 26, 2021
Choosing optionality over arbitrary goals
Why I'm choosing to stop writing this newsletter on such a frequent basis
September 19, 2021
Generating Momentum Part II: a portfolio approach to building momentum
How to know when to double down on projects, when to experiment with changes, when to put them on autopilot, when to pivot them, and when to kill them.
September 12, 2021
Jobs where former founders have unique advantage
The rare assets that former founders have and the jobs that need those assets the most
September 5, 2021
Content medium-distribution fit
An argument for finding distribution based on first identifying your ideal content medium, not the other way around.
August 29, 2021
Side projects as cross-training
How side projects can make you better at your day job
August 22, 2021
Generating Momentum Part I: Managing perceived momentum
How entrepreneurs can generate more momentum by managing perception and expectations
August 15, 2021
Resilience as an entrepreneurial skill
How resilience – which is better than persistence – can be worked on.
August 8, 2021
Why resourcefulness is the most important skill for entrepreneurs
And how like any skill, it can be learned
August 1, 2021
Value creation vs. value extraction
Why forgoing value extraction leads to a bigger pie for everyone and more serendipitous outcomes
July 25, 2021
Persuasiveness as a skill
Being persuasive is a skill that enables entrepreneurs to be good at the many hats they wear; here's how persuasiveness breaks down and how it can be fortified
July 18, 2021
Claiming false starts instead of pushing through slow starts
How you can use false starts to take ownership of your career narrative – rather than trying to push forward after a slow start
July 11, 2021
Assessing and acquiring the credentials to accelerate careers
Being intentional about acquiring credentials that will help with future endeavors
July 4, 2021
Creating artifacts that accelerate your career
How entrepreneurs crystallize their experiences and insights into domain expertise
June 27, 2021
Consistency without experimentation is a treadmill
It’s easier to hold to your principles 100% of the time than it is to hold to them 98% of the time.
June 20, 2021
Developing domain expertise by reducing writing surface area
And a deep dive into the themes in this newsletter
June 13, 2021
Building a portable audience
Why and how we can build portable audiences through our current gigs which we can take with us for future endeavors
June 6, 2021
Unpacking VFA's secret sauce in getting 20somethings to start companies
Why focusing on cultivating friendships is more effective than prescriptive guidance
May 30, 2021
Nobody cares about what you're building
A dumb-simple mental model for being more efficient in building things
May 23, 2021
How agents, communities, and collectives are helping entrepreneurs diversify
And why entrepreneurial careers are about to become far less risky.
May 16, 2021
Evaluating side projects to improve their returns
6 months into writing this newsletter, I did a self-evaluation to figure out how to increase the ROI of this side project without additional investment
May 9, 2021
You're moving on from your startup. Now what?
A framework for navigating to the next chapter of your career after moving on from your startup, with reflections from my own experience.
May 2, 2021
Part II: Cultivating superpowers to maximize career trajectory (self-evaluation)
Applying a framework for identifying potential superpowers
April 25, 2021
Cultivating superpowers to maximize career trajectory
What watching Andrew Yang's ascent has taught me about cultivating superpowers
April 18, 2021
Being mentally ready to start a company
Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.
April 11, 2021
Dealing with risk asymmetry between founders and investors
How investors will increase the chances that a startup fails, and how founders can benefit from that dynamic
April 4, 2021
7 aspiring founder personas
A framework for getting ready to start a company (including my own self-assessment)
March 28, 2021
How startup failure can help founders expel toxic traits
Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes frameworks, analyses, profiles, and musings about building entrepreneurial careers. This isn’t just startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal.
March 21, 2021
Don’t look for co-founders; make friends
How to go about finding co-founders months or years before starting a company
March 14, 2021
Preserving optionality to find harmony
How entrepreneurs should consider the loss in optionality when making commitments
March 7, 2021
Why entrepreneurs should improve their writing
If I had to pick one skill to encourage any aspiring entrepreneur to develop, it would be writing.
February 28, 2021
Side projects as a lever for professional growth
and why employers should embrace side projects
February 21, 2021
The inaccessibility of entrepreneurship and using side projects as a back door
Entrepreneurial opportunities are not as accessible as they're made out to be, but a more liberal interpretation of side projects can make entrepreneurship more accessible
February 14, 2021
Entrepreneurship is a skill, not a switch to flip
Entrepreneurial muscles are either non-existent, being strengthened, or atrophying
February 7, 2021
Three Rules of Entrepreneurial Diversification
When and when not to diversify time into side projects
January 31, 2021
This newsletter is not yet good
The benefits of proactively seeking negative feedback to remain intellectually honest
January 24, 2021
Founder/Product/Market fit
Why we as founders are an overlooked but equally important consideration in the hunt for product/market fit
January 17, 2021
Maximizing entrepreneurial progress by systematically de-risking
Why focusing on KPIs can be misleading and why it's better to focus on constantly de-risking
January 10, 2021
Making progress on ventures before even starting
How entrepreneurs can de-risk ventures years before starting them
January 3, 2021
Everyone is an Investor
Everyone with an entrepreneurial career – from investors, to founders, to startup employees – are investors. We can learn a lot from investors on building entrepreneurial careers.
December 27, 2020
Using Intellectual honesty to maximize the value you get from your asks
How being truth-seeking about the value you will provide to others will help you calibrate your asks
December 20, 2020
Creating personal flywheels to grow entrepreneurial assets
Finding harmony between passions, side hustles, and day jobs to accelerate your career as an entrepreneur
December 13, 2020
A Conversation with Noah Shanok, Founder of Stitcher
Noah talks about his journey building Stitcher, what acquisitions actually look like, dealing with burnout, and figuring out what's next after building a startup.
December 6, 2020
Why and how to maximize the opportunity costs of starting a startup
A framework for thinking about day jobs vs. side projects to make sure your next startup has high initial investment
November 29, 2020
Entrepreneurs as 1-person Venture Studios
Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes essays, interviews, and more about building entrepreneurial careers. This isn’t startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal. I’m a former startup founder, the co-author of a book on seed fundraising, and am on the Early Stage Startup team at AWS.
November 22, 2020
Writing as an onramp to building a startup
Hi - I’m Mike Wilner, the writer of this post which is part of my weekly newsletter, Getting Shots Up. The newsletter includes essays, interviews, and more about building entrepreneurial careers. This isn’t startup advice – it’s a zoomed out view of how entrepreneurial people can think about constructing a career that results in a lot of high quality shots on goal. I’m a former startup founder, the co-author of a book on seed fundraising, and am on the Early Stage Startup team at AWS.
November 15, 2020
Why my best move as a founder was giving up
Two and a half years after moving on from my startup, here is the reflection on the benefits I experienced by moving on when I did rather than sticking with it.