How to compete in an overcrowded market 🤼‍♂️ (Startup Watching #248)

By Andrew Askins • Issue #248 •

Happy Friday Watchers!

I learned a tough lesson this week.

When you provide feedback to one of your direct reports, make sure you can provide specifics.

If you can’t, then you don’t have enough information yet or your feedback is invalid.

I gave some critical feedback to a team member this week, and when she asked for specifics I had to admit I didn’t have any. As I thought about it I realized I had likely misread the situation and my feedback was off base.

I apologized and laid out a plan for what I would focus on instead. But at that point I had already damaged the trust I have with them, and made their day a little worse.

The tricky part about management is you have to practice to get better, but the only way to practice is with real people.

Best from Charleston ✌️

Andrew

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bubble.io • Share

MONEY

How a designer and YouTuber makes her money 💰

Charli Marie is the marketing design lead at ConvertKit and also runs a successful YouTube channel and podcast where she talks about design. She went super transparent in this blog post and broke down how much money she made last year and exactly where it came from. I love seeing this kind of transparency!

charlimarie.com • Share

The laws of investing 📈

This is a huge post from Morgan Housel about the fundamental laws of investing. There’s some really good stuff in here that goes counter to the standard cookie cutter advice you see.

www.collaborativefund.com • Share

LEADERSHIP

Don't solve problems if you want to be a great manager. 🦸‍♀️

This is one of the posts that’s most on my mind this week. I’m constantly having to remind myself to stop trying to solve problems and instead act as a coach and guide. Because what makes a great manager isn’t the problems they solve, but the questions they ask. Start with these 16 questions here.

knowyourteam.com • Share

Reflections on being a female founder 👩‍🎤

This is a super raw look at what it was like for Tracy Young to grow PlanGrid as a female founder, but it’s also one of the most raw looks at being a founder in general that I’ve read in a while. You can feel the energy behind the words.

tracy.posthaven.com • Share

GROWTH

How Glossier reached triple-digit annual revenue 💄

The latest from my good friend Laura Bosco. She dives into Glossier’s use of customer feedback loops and the way they’ve built a brand that feels like your BFF.

www.learnwhy.co • Share

How to compete in an overcrowded market 🤼‍♂️

Asia Matos is the founder of Demand Maven, a growth marketing firm that specializes in helping SaaS companies get to their first $10k in MRR. Asia knows her stuff, and she goes way deep in this thread breaking down lessons learned from an attempt at helping a recent client break into an extremely crowded market (project management).

demandmaven.io • Share

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By Andrew Askins

Curated knowledge, inspiration and background stories from the startup world. Delivered to your inbox every Thursday or Friday 📬 | Find me @andrewaskins.

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How to compete in an overcrowded market 🤼‍♂️ (Startup Watching #248)

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Zoom doesn't have product/market fit?? 🤯 (Startup Watching #247)

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The secret to being a prolific creator is right in front of you 👀 (Startup Watching #243)

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