Once More, With Feeling

Start-up lessons, the importance of self-honesty, raw journals, pitching products.

Dear Readers,

I hope your entry into the new year was just what you intended — whether reflective, relaxed, jubilant, or simply relieved.

My 2022 was full of growth. What does that mean? A few visits to the Pit. A few summits to the peak. A whole lot of learning.

In 2023, my goal is to continue that journey, but with more honesty and transparency.

I’m realizing it starts with me first: honesty towards myself. We all have self-deceptions. These defense mechanisms provide us comfort.

It struck me that true self-acceptance can’t come without true self-honesty. And there are ample examples where I am not fully honest with myself:

1. Brushing aside, judging or justifying my feelings
2. Self-censoring opinions
3. Not proactively asking for feedback
4. Externalizing problems rather than seeing my role in them
5. Avoiding observing myself.

Of course, I have been on the other extreme too — too much self-judgement of the above, feeling guilty for feeling this or doing that.

But judgement is not honesty.

Honesty is curiosity, and then awareness, acknowledgement, and accountability. Not ‘good’ / ‘bad’ labels.

Letting go of judging labels requires trusting that somewhere deep down, the self knows the path. The self sees something lovely and fulfilling about the journey and even its hardest obstacles.

This year, I hope to spend more time in dialogue with that self.

What does that mean for The Looking Glass, and what can you expect?

More raw stuff here. More exposure to the inner workings of a start-up founder’s journey. But please give me feedback. What do want to hear more of?

You might have noticed that I’ve turned on paid subscriptions. While much of my writing will continue to be free, I’m looking to hire someone part time to help me wrangle this newsletter and take care of the publishing logistics so I can put out words more regularly.

If you’ve followed me for a while and gotten something out of my writing, I hope you’ll consider subscribing. It’s $6 a month, less for a year. Consider it a gift of a fancy third-wave coffee every 4 weeks. I am highly motivated by coffee :)

With that, let’s get to some recent ideas.

Start-up Life = Hard Won Insights

Twitter version; LI version

1. Doing well at a start-up is not simply about skill, it is about mentality.
2. A start-up mentality values action over correctness, results over process. It suits those that value autonomy over clarity.
3. Start-ups operate in wartime, not peace.
4. Founders must therefore lead from the front — charge into the mud, make decisive calls, and survive to battle another day.
5. To maximize learning, you need to doubt your knowledge.
6. To maximize creative production, you need confidence in your knowledge.
7. The inner game is maintaining this in balance.
8. Transparency and vulnerability are the fastest ways to earning trust.
9. Don’t hide problems. Run towards them, expose them to light and conversation, and marvel in the power of communal support.
10. Top performers like accountability.
11. Accountability means caring, it means excellence matters, it means a commitment to something greater than ourselves.
12. We care about data because we feel a deeply human need to be masters of our own destinies.
13. Analysis in the face of uncertainty is one way we wrest control from the whims of fate.
14. A great company fulfills a win-win exchange: individuals give their talent, effort and heart toward a purpose they find more meaningful and rewarding than the satisfaction of individual egos.
15. Being “successful” in a particular role at a particular company in a particular chapter of your life is not a reflection of your worth as a person.
16. We can be objective about the effectiveness of a particular fit while maintaining love and respect for each other as people.
17. The price of rapid improvement is repeated failure.
    Doubt and discomfort are the entry price of excellence.
18. It’s your choice to play this game, of course. But if you do, recognize that there are no shortcuts to hard work and struggle.
19. You sometimes feel things earlier than you can logically articulate them.
20. Trust yourself enough to explore the feeling and learn something from it.

Talking Excellence with Kunal Shah

If you don’t know Kunal, he’s a serial entrepreneur (currently building Cred, which processes about 20% of the cred card payments in India) and someone I’ve gotten to know and admire as an insatiably curious voice (just check out his Twitter). In this rooftop chat, we discuss everything from what I think about ChatGPT to the price of excellence.

Manifesto for the Data-Informed

I shared the core ideas some weeks back, but now see it beautiful rendered and with its own nifty URL: https://datamanifes.to/! I truly believe that if we all fully internalized these values, we’d see the productivity and creativity of organizations everywhere skyrocket.

Many thanks to Jay Mo and Deepankar Bhade for giving this page love and soul.

From the Archives: Pitching a Product Idea

Q: Our team is planning for next year. What tips do you have for how I can present my product ideas effectively to the team’s leaders so they’ll get support?

While nobody likes to admit to judging a book by its cover, there is no denying that the same product idea can be presented in a compelling way that gets a room yelling “where can I sign up to build this?” or be described in bland, uninspiring terms that leave folks wondering “What’s the point?”

Communication matters. Here are a few ideas to help communicate product ideas effectively:

Describe the problem you’re solving.

Every product should have a reason for existence and a story for why people’s lives will be better after this product comes to the rescue. But before you can talk about the superior future you want to create, you should set the stage by describing the dismal present we currently living in.

Envision the start of an infomercial, where people are stumbling around in black and white, wallowing in tears while cutting onions… because they don’t yet have the Slap Chop!

Or imagine the problem statement for ride-sharing apps: “Getting a taxi is sooo hard. How many times have you stood by the side of the road (sometimes when it’s rainy or cold outside!) holding out your arm, only to see taxi after taxi driving by already occupied? You feel annoyed, maybe anxious. You have an appointment in 20 minutes, and who knows how long this is going to take? Maybe you should drive? Ugh but parking takes forever as well, not to mention it’s expensive!”

Stories like this paint an instant picture of what people are doing today, and why today’s world isn’t ideal.

Even if you’re building products for people who aren’t like yourself, it’s important to set the stage, ideally through research. Research helps us build empathy with customers. Perhaps your products are for business users (not consumers) or people living in different countries. Gather and share stories of real people, what their lives are like, and what problem they’re having that there isn’t a great solution for. This is most powerful when you include quotes, pictures, and a clear depiction of what people are trying to do, and why it isn’t working for them.

Describe how many people have this problem.

Now that you’ve broken it down to human terms, the next step is to expand this with market research to show just how large this problem is…

Continue reading…

Daily Moments

A snapshot of 5 recent journal entries, for subscribers only.

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