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Maximizing Productivity: Insights from a $30M CEO's Toolkit

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Chapter 1: The Call from My Ex-CEO

Two months ago, while I was engrossed in writing an article, an unexpected call came through—my former CEO. He built his company a decade ago and sold it for an impressive $30 million during the pandemic (I had the privilege of working under him for five years). Now, he’s diving into startup investments and exploring new ideas, which is what prompted his call.

"I'm crafting a presentation to attract investors, but I’m not satisfied with its current look. I quickly threw it together in Google Slides, but it definitely requires some refinement. Could you lend a hand?"

I was both surprised and eager to assist. I have immense respect for my CEO, and we share similar values. However, I was about to go on paternity leave the next day, and we had family travel plans across Europe in just three days. He needed the presentation completed within a week. Ultimately, we managed to connect over Zoom, where I gained valuable insights and guidance during our conversation.

We discussed his return to the entrepreneurial scene, as he looks to launch a new venture. I took the opportunity to inquire about his current favorite productivity tools. I had previously documented this two years ago and thought it would be fascinating to compare his toolkit as a startup CEO back then versus his current role as an investor/adviser.

A Quick Recap

Here’s a brief overview of the five productivity tools my CEO couldn’t live without in 2021:

  1. Garmin Fenix 6 Pro Solar: He loved to boast about his fitness, claiming to have the stamina of a 25-year-old despite being 50.
  2. Notepad: "I find note-taking on my phone cumbersome; it’s too small."
  3. Nike Revolution 5: "Switching from dress shoes to sneakers significantly boosted my efficiency."
  4. Google Calendar: He meticulously planned his week in blocks ranging from 15 minutes to several hours, often from 7 AM until 9 PM.
  5. Wake-up Light: "This gadget is essential for getting out of bed early, especially in winter."

The Updated Toolkit

Fast forward to our latest discussion, here’s the updated toolkit he shared with me:

  1. Google Slides

    "I’m utilizing Google Slides much more frequently as an investor than I did as a founder. I’m constantly reviewing pitches and assisting emerging founders in crafting their presentations. It’s an efficient way to share ideas and feedback. Plus, since everyone has a Gmail account, collaboration is seamless."

He highlighted the advantage of tracking version history in presentations, allowing for easy reversion to earlier drafts. Although he believes his designs are subpar, he relies on a pre-existing template called "Prototyping Presentation" from Google’s library.

"This template typically contains 90% of the slides I require for pitches, and I simply delete the unnecessary ones. It’s perfect for drafting, and I also recommend it to founders seeking my advice."

  1. Pocket

    Pocket is a fantastic bookmarking tool that allows users to save online articles for later reading.

"I realized that as an investor/adviser, consuming a significant amount of reading material is crucial for making informed decisions. Previously, I only read at night, but now I dedicate several hours each day to industry-related content, saving everything in Pocket."

He maintains two lists in Pocket:

  • Inspiration: For articles he has read and finds valuable.
  • To Read: For lengthy content he encounters during the day but doesn’t have time for; he usually revisits this at night.

He appreciates the ability to highlight content and easily access his past highlights. I too regularly use Pocket, and interestingly, my CEO reads saved articles on the same type of device as I do—his next essential tool.

  1. BOOX Note Air3 C

    "I use this device to read saved articles from Pocket in bed. I prefer not to look at a regular screen before sleeping, and this tablet mimics the appearance of paper. I can read comfortably with my bedside light on, and I also jot down notes in bed, as reading sparks many ideas."

Although he mentioned a traditional notepad as a necessity in 2021, he now prefers his E-ink tablet for nighttime reading. During the day, he still uses a notepad, as he finds phone note-taking impractical, opting to filter important notes on his tablet later.

Priced at $500, the BOOX Note Air3 C is an investment, but as my CEO pointed out, it’s worth it. The technology has significantly improved since my girlfriend and a friend purchased earlier versions, which suffered from slow refresh rates.

"An E-ink device is unparalleled for nighttime use. It feels more natural to read, devoid of blue light that disrupts sleep cycles."

  1. GARMIN MARQ Commander Gen 2

    "This was one of the first high-end gadgets I bought after selling the company. I had a previous Garmin watch, and as a fitness enthusiast, I simply googled ‘most expensive Garmin watch’ and bought it. While it’s pricey, it’s a fraction of the cost of a Rolex, offering far greater functionality."

It didn’t shock me that my CEO invested in a Garmin watch, as he’s never been one to flaunt wealth (he still drives his old family car). He’s committed to fitness, showing up for every sports event during our startup days.

"This watch includes many preloaded maps my previous one lacked. I prefer varied running routes, and it’s ideal for long-distance running. Ultimately, anything that enhances your productivity, health, or activity is an invaluable investment in yourself."

  1. Philips Grind & Brew Coffee Maker

    "I have a funny story about this. As CEO, I was always the first to leave home, enjoying my morning coffee at the office. After selling the company, I began spending more time with my kids and wanted a smoother morning routine. I wake up at 6 AM, and I didn’t want to waste time setting up a traditional coffee maker. So, I bought this fantastic machine that only requires water to be filled once a day and coffee beans every two weeks. I set the timer for 6 AM, and it handles everything else!"

This brought a laugh, as I had never pegged my CEO as a coffee lover. Like him, I struggle to find time for morning coffee with a baby at home, often forgetting to prepare the night before.

In conclusion, it’s intriguing to see how many items from my CEO’s current toolkit mirror those from two years ago. He still cherishes his Garmin watch but has upgraded to a pricier model. Google Slides has supplanted Google Calendar for prospect communication, reflecting a reduction in meetings. He maintains a notepad but prefers his E-ink tablet for a more digital approach. The coffee maker and wake-up light both cater to early mornings and waking up refreshed.

As I noted two years ago, simply acquiring the tools mentioned here won’t instantly transform you into a millionaire CEO. This article is about inspiring you to experiment with various productivity tools and techniques. Embrace what resonates with you and discard what doesn’t; remember, individual needs vary.

Thank you for reading, and I wish you success on your productivity journey.

I interviewed 50 productivity/business experts and compiled a comprehensive 150+ page guide filled with practical advice from those who excel in productivity. Download it for free here.

Discover the productivity system of a CEO making $20,000 a month, including essential tools and techniques.

Watch as a CEO reads Glassdoor reviews, gaining insights into company culture and employee feedback.

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