Mark Bakker | B2B SaaS

Co-Founder and Managing Director at Coho Growth. B2B SaaS. AltMBA Alumni.

[Andrew Wilkinson @awilkinson]

For years, I've struggled to journal. Most people I know do.

It's hard to just sit there with a blinking cursor and barf out your thoughts accurately every day.

But my friend Charlie Grinnell (@CharlieGrinnell) has cracked the code. He's built an amazing workflow that allows him to build a huge database of his thoughts and feelings using Reflect + OpenAI, and even crafted his own AI therapist that he uses to work through problems at work and in his personal life.

We break down how he built this, and many other nerdy things, in this week's podcast.

This one is for the nerds. If you're into workflows, this is your jam.

Here's some key insights:

• AI's biggest impact may be personal productivity, not job displacement
• Charlie's innovative journaling system using voice memos and randomized prompts
• How to build a "second brain" by connecting notes, highlights, and AI
• Using AI to chat with your past self and apply lessons from books you've read
• The power of specific prompts to get better results from AI tools

Charlie's approach shows how intentional systems can unlock creativity and learning.

The future of productivity looks bright - imagine an AI assistant that can:

• Manage your digital life seamlessly
• Synthesize information across all your tools
• Help you take action on ideas and insights

Topics

00:00 - Intro
00:33 - Getting to Know Charlie
03:17 - Charlie’s Typical Day
05:15 - Charlie’s Journaling Routine
11:56 - Charlie’s Library of Journaling Questions
13:48 - Facilitating Deep Work
15:39 - Dealing With Low Priority Tasks
20:09 - Avoiding Distraction While in Deep Work
21:19 - Time spent in Deep Work
21:47 - Charlie’s Favorite Type of Deep Work
23:19 - Meeting Recordings, Transcripts, & CRMs
26:48 - Charlie’s System for Reading
31:35 - Keeping Track of Interesting Podcast Tidbits
34:22 - Dealing With AI’s Recency Bias
35:57 - How Charlie Keeps Consistent With His System
38:11 - What Drives Charlie to Create Systems
42:18 - Broken Parts of Charlie’s System
44:00 - What Charlie’s Looking Forward to With AI
45:55 - Other Interesting Ways Charlie Uses AI
49:30 - Products Charlie Really Loves

[Mark Bakker | B2B SaaS @markbakker]

@JordanGal UniFi!

[Mark Bakker | B2B SaaS @markbakker]

@jayyeh I'm looking forward to your Venture Debt webinar. Have you heard of us? We offer debt without warrants, a sponsor, etc.

[Mark Bakker | B2B SaaS @markbakker]

@awilkinson We have a monthly yield fund providing loans to growing B2B SaaS companies. Our 7-year track record is 14% net to investors.

[Mark Bakker | B2B SaaS @markbakker]

@awilkinson Holey Grail Donuts near Hanalei Bay

[Mark Bakker | B2B SaaS @markbakker]

@awilkinson Because I'm raising a (debt) fund: Thomasz Tunguz on Venture Unlocked. He talks about even though he has a track record at Redpoint, still hard to raise capital. https://t.co/wow4YLCxL2

[☔🔥☔ @kirbywinfield]

techstars billion dollar outcomes by program:

boulder: 4
seattle: 3
nyc: 3
boston: 2
r/ga: 2
kaplan: 2
cloud: 1
chicago: 1
austin: 1
london: 1

sf: 0
la: 0

[☔🔥☔ @kirbywinfield]

techstars shutting down hundreds of accelerators where they're the only game in town...

...to focus on the markets where they're needed least.

good luck with that deal flow lol

[Mark Bakker | B2B SaaS @markbakker]

@agazdecki Hey Andrew, would love an invite! In the process of launching a new venture.

[Mark Bakker | B2B SaaS @markbakker]

@einarvollset Picked up water skiing 3 years ago. I'm getting better, but it brings me to beautiful, quiet places that I can truely relax. Amazing start to the day as well!

[Mark Bakker | B2B SaaS @markbakker]

@Shalinsky @liamcode Hell yeah brother

[Christopher Lochhead 🏴‍☠️ ✍🏼🎙 @lochhead]

According to HBR (not exactly dummies),

the top 0.1% performing startups have 45 year old founders. 

(let that swizzle around in your head for a sec)

[Jason Cohen @asmartbear]

"Smart Bear" was too dorky for Frank.

He suggested "Software Test and Deployment Systems, Inc," or STDS for short. For real.

Smart Bear was bought for nearly $2B in 2020.

Still called Smart Bear.

https://t.co/HG8Lc5j8hk

[Mark Bakker | B2B SaaS @markbakker]

Forest fire float planes #fire #bc #forestfire @DNorthVanFire

[Christopher Lochhead 🏴‍☠️ ✍🏼🎙 @lochhead]

Entrepreneurs

Don’t be fooled by Gary VeeDee or any other
“personal brand" hustle porn star.

It's all a lie to sell you BULLSHIT you don't need.
👊🏴‍☠️

[Mark Bakker | B2B SaaS @markbakker]

@donutmedia check out how sick this Suzuki is! #northVan #vancouver

[Andrew Wilkinson @awilkinson]

I started my company 16 years, 3 months, and 5 days ago.

Today, it went public.

But let's rewind for a second...

5,939 days ago, I was a barista at a small cafe called @2percentJazz2, in Victoria, Canada.

I made $6.50 an hour.

Two guys, Chris and Jeff, started coming into the cafe.

They'd sit there all day drinking espresso and typing away on their laptops, using the wifi.

After weeks of this, I asked them what they did for a living.

Didn't they have jobs?

They told me they were "web designers" and this — sitting on their laptops — was their job.

As I dug in, they told me how it worked:

They asked local businesses if they needed a website, then charged them a couple thousand bucks to make one.

They could whip a website together in a few days, and each make $1,000.

Simple.

This blew my mind.

And at that moment, I realized something:

I wanted to be the guy drinking the espresso, not the one serving it.

Chris and Jeff were clearly smart, but I knew some basic HTML and figured I could do the same.

I decided to try it out.

When I got off my shift, I took the bus over to a book store downtown and bought a book called 'Bulletproof Web Design' by Dan Cederholm (@simplebits) to hone my skills.

Then, I googled "freelance web design jobs" and found a tech job board called Authentic Jobs made by this guy in Utah, @cameronmoll.

There were hundreds of posts, mostly from startups in San Francisco, looking for freelance web designers.

I decided to try to win one of these contracts, but I had a critical insight:

Nobody wants to hire an 18-year-old barista to build their website.

So, I decided I'd create a fake design agency.

Using tricks from Dan Cederholm's book, I whipped together a slick looking site and called my "agency" MetaLab (after the <meta> tag in HTML).

The website was very vague as to what exactly MetaLab did, who worked there, or where we were located.

It also featured a cringe-inducing tagline "We Help People Make Cool Stuff."

Like an email spammer, I started sending emails to every single web design job post I could find.

I was met with crickets, until I got an email from a guy named Kavin Stewart (@kavinstewart).

He worked at a startup called Offermatica in San Francisco and told me he needed an interface designed for a web app.

I barely understood what a web app was, but I assured him I could do it.

He proposed a $2,000 USD budget and my eyes went wide.

This was more than I earned in a month, and the project was just a few days of work.

I walked into the cafe the next day and quit my job.

I told myself that if I could just make enough money to wake up whenever I wanted and comfortably make rent, I'd be good.

The rest is history.

But I slightly overshot.

I still own MetaLab, but along the way me and my business partner @_Sparling_ started dozens of companies, then began buying wonderful businesses, including one (Dribbble) — amazingly — from Dan Cederholm, the designer whose book I bought when I first started.

Today, Tiny went public, and as of this moment has a market capitalization of just under $800 million.

I can't even begin to explain how mind boggling this is to me.

This has not been a feat of entrepreneurial genius.

My key skill has been choosing incredible people to work with, both internally and externally, and I wanted to say a huge thank you to everyone who has worked at Tiny and our various companies over the years.

And a special thanks to @simplebits, @cameronmoll, and @kavinstewart for helping with my first step😉

Watch for us on the TSX Venture Exchange under the ticker TINY (how cool is that ticker?).

https://t.co/tlpgiEO2MU

[Scott Yewell @syewell]

My partner @einarvollset recently gave a talk to a select group of B2B SaaS owners about when to sell your business... Some great insights in here: https://t.co/jWumotemBB

[Mark Bakker | B2B SaaS @markbakker]

@awilkinson My friends have this at their house and old business. Vancouver Island built. https://t.co/X6sTrgZgMk