Entrepreneurship in early stage is hard
Reflecting on the struggles and realities of entrepreneurship and managing expectations.
Running a small business
This past week I have been reminded again what it feels to be an entrepreneur through multiple conversations with fellow founders. I have been doubting my relevance to the role as my career went on a different tangent in the last 2 years.
So, I have some bits of self doubt when I engage in conversations with founders trying to unpack their problems. It is a really difficult role and you find no empathy from people since you chose it upon yourself. Especially when you go out on your own as a solo founder.
The expectation of the role and responsibilities of shouldering a business really take a toll, even on the best. The ride gets little less bumpy when you have funding but that is not the case for every entrepreneur. The domain where I interact has a problem of being complex and hard to execute.
A long time ago, I tweeted a short lived thread on running a small enterprise. I didn’t have it handy during last week’s conversations but decided to revisit them for the purposes of presenting a more coherent version to be referred in the future.
Being optimistic about your chances and while pessimistic of the outcomes is default state of mind while running a small firm. 8:14 PM · Sep 5, 2020
This is an apt representation of the mental state of any founder in the seed stage. The state of startup wavers between extremes. Being optimistic pays but in moderation.
The Flywheel of wins generate momentum which is infectious. Similarly the hurdles that stall are disastrous. In small companies you see them happening simultaneously. 8:31 AM · Aug 11, 2020
Pessimism seeps into the psyche of the team when the hurdles stall the momentum. Hence, managing the expectations becomes key and it begins with the founder.
Expectation management is a core facet of building companies. Most important aspect of this particular ask is managing your own expectations. 3:46 PM · Nov 23, 2020
There is often the case when founder in the spirit of benevolence, especially because they care about the team, shield the team of the existential challenges that are being faced by startup.
Exposure to problems, tradeoffs and impact is what helps team to huddle up together and solve things. As a leader it’s your job to get them as much exposure as possible. Instead, we have the habit of curation. And then complain no one is coming up with ideas. 2:03 PM · Dec 4, 2020
If people leave at the onset of being exposed to this level of challenge. The synthesis would be that the hire wasn’t right fit for the role. No point haggling over the hire and trying to convince them.
In the end the choice a founder makes to start a venture is totally on their own volition.
Working on something of your own is immense privilege. Victimisation of self for working long hours is on you. Not the fault of anyone else in your life and especially not your team. 11:05 AM · Oct 7, 2020
The way to honour this privilege would be to increase the learning curve of the enterprise and the team that decided to join the journey.
Round up
Career lessons for me and you
This post was written first when I shed my role as an entrepreneur. It was a riff on the post that Nirant K wrote about “Act Like 35”. This last week he wrote an another thread on career which I found fascinating since it is relevant to my current career trajectory.
Too many folks feel stuck because they're trying to change too much in their career.
— Nirant (@NirantK) November 22, 2024
But how to prioritize? Here's how I help my friends do this:
Your career is a combination of Function, Industry, Geography.
You can change one of these. Not all three at a time. pic.twitter.com/nCbz696zon
Unknowingly I have traversed the same path in recent past and passes the believability rubric since the best also follow this approach as I reflect on their trajectories.
Links that resonated
Anxious Founder Loop
Long time ago James Rosen-Berch tweeted a thread about patterns that would kill a company. One of the systems of anxious founder loop really touched a nerve for me when I running things at Subjimandi.app.
eventually, the endless fires and feeling of rudderlessness explodes and results in the founders (or mgmt, if at a lower org level) feeling like they're losing control.
— James Rosen-Birch ⚖️🕊️ (@provisionalidea) May 10, 2022
a crackdown often ensues, that gravely exacerbates the problems they're trying to fight. pic.twitter.com/Xj9SxIFvD5
In anxious founder loop you see that founder has multiple communication and feedback loop failures. This results in lack of clarity and direction. Team will be engaged in continuous firefighting and give up eventually.
Sign off
I skipped last week because I was busy with last minute travel to Chennai. I met couple of founders during the weekend which was the genesis for the topic.
I blew past a significant hurdle to move on to the next phase of my life.I have many questions to answer myself first before I can shed more light on it. This post by Karthik of pertinent observation is what I read before my visit. It prepared me really well for my own ordeal. Ironically my own experience mimiced the one shared by Karthik.
Signing off till next time,
Vivek, going down the memory lane.