The ending is really another beginning
Hey all, how are you?
I’ve been doing some soul searching in the last 2-3 weeks. I talked to some old friends, did some journaling, explored tens of ideas in my head, made lists of my strengths and interests, recorded some fun Youtube videos etc. as I was slowly coming to a reckoning with my latest circumstances.
Ultimately the good news is I have finally arrived at clarity on what I want to do next. In today’s edition, I will share what happened that led me to this ‘period of wonder’ and what I intend to do the next few months.
CONTEXT
First, let’s zoom out. It all started when I realized that my time at On Deck was coming to an end by the end of May. On Deck has had an unfortunate series of events.
But as I reflect on my time there, all I can think of is how it was the best launchpad for my career. On Deck took a shot on me when I was relatively unproven and helped me become the brand that I am. (humble brag? Sure!)
Erik and David are not perfect but I adore them for how much they believed in me and how they gave the keys to the kingdom when it came to ODNC. With that powerful autonomy, a deep sense of mission and a strong spirit of service, I went to work every day and lead my team with confidence. I was the first outside hire to plan and launch an entire new Fellowship program in less than a week of joining. It took over Twitter and quickly became one of the most profitable and buzzing no-code communities on the planet. My goal was to make no-code even more mainstream and I believe I achieved that. Many of our fellows achieved life-altering outcomes that put no-code on the global map. And we minted new no-code superstars. You’ll see some faces and case studies on this website.
So by end of May, I went off deck from On Deck. I wrapped up one helluva career chapter with so many impressive milestones and learnings. And I got to serve a truly world-class community of builders, makers and no-code founders. My team and I worked with one soul .. as one unit. We set some unprecedented NPS records at On Deck. I loved my customers(Fellows) so much and they loved me back. Here’s proof.
THE ENDING
Well, all good things have to come to an end one way or the other. So June 1st, I found myself unemployed and wondering what’s next for me. I wasn’t going to rush into something immediately as I had just hustled my ass off for 1.5 years and needed a bit of a recharging break. I took time to reflect on my circumstances. Meanwhile, the news about my leaving On Deck spread and I kept getting strong inbound leads from founders and startups who wanted me on their roster.
This felt exciting. I never felt *this* wanted in my career before. Thanks to both my pedigree but also my 33,000 audience on Twitter who helped me with connections.
But I was in a unique dilemma.
THE CROSS ROADS
Should I start a new startup?
I felt skilled enough and experienced enough to pull this off.. but something felt strange. I wasn’t ready enough. I didn’t have enough conviction on any one of my ideas in my head. I do have tremendous social capital in certain niches (like no-code, ed tech, community mgmt) but something in me keeps bugging me that I am not ready to take the leap.
Or should I take up another job at a startup?
I frankly don’t need any extra experience of working at a startup or leading teams if ultimately my goal is to found a new startup. But I could use a steady job and more practice in the ‘market’ serving customers though content and community (which are my strengths). I also think I can help the right company accelerate towards it’s mission.
I struggled with this dilemma for 2-3 weeks which is when I did my soul searching. I asked myself if I was being afraid to take the leap into starting a startup or if I was being thoughtful/practical. I asked myself if I was wasting precious years of my life NOT founding a startup and only delaying that chapter. However, after many conversations with close friends and my family, I arrived at some clarity based on the below framework built on self-awareness and honesty.
What I don’t want to do?
blindly announce that I’m starting something new and begin fundraising
leverage my existing connections/network to raise a pre-seed round (I believe I can pull off a pre-seed easily even in this market)
delude myself with a compelling narrative and a pitch deck and think I have an idea worth going all in for.. purely based on gut feeling or my expertise in a domain (ex: no-code)
What I do want to do?
be humble and admit that I may have all the leverage but it won’t do any good if I take on unproven ideas without validating demand first
be realistic that I can’t take blind risks since I have a family to feed and a kid (real responsibility)
spend time building out a series of small bets on new ideas and actually validate them if they can be businesses
wait patiently until I can find signs of PMF and then raise a round to go full-time
until then serve another company’s mission that’s exciting to me and help them win while also getting paid and keeping lights on (for family!)
Note: If the above resonates with you, check out this doc and hit me up.
This framework was helpful along with some re-affirming conversations with my close friends. That brings us to today.
THE BEGINNING
I finally arrived at a much needed clarity moment this morning so wanted to document it both on Twitter and on this newsletter.
I decided to pursue two tracks ahead in conjunction:
Join a company with an inspiring mission/great culture where I can shine and add tremendous value to customers (aka dream role .. see tweet below)
2. Experiment with small ideas on the side to find a big problem with a magnetic pull that’s worth going all in for. Spend the next 12-18 months on this track.
I intend to intentionally begin both these tracks today.
I would also love to document my experiments, results, learnings (both wins and losses) on this newsletter so sign up if you haven’t and stay tuned. Follow me on Twitter for more real-time updates.
Hit reply and let me know if you are also on a similar journey or if you have just gotten off this track and started something new. Would love to hear your stories and learnings.
Originally published on KP's Column · Jun 12, 2022