Mark Bakker | B2B SaaS

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

@JordanGal UniFi!

Any recs for a home wifi mesh system? I got the Eero a few years ago and it was good at first, now not so good. What's the move?

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

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

Cashflow-focused Investors: How do you position your yield-focused public portfolio? Any clever trades beyond big dividend stocks + treasuries?

@awilkinson Holey Grail Donuts near Hanalei Bay

Anyone interesting on Kauai right now up for a coffee this week? Also: would love recommendations for food / drink / activities :-)

@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. open.spotify.com/episode/7guaO9…

What are the most impactful podcast episodes you’ve listened to in the last 6 months?

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

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

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

Things to note: Last year we hosted about 100+ founders. We're bringing back the taco truck. This has somehow been approved by my wife again. Event will start in light mode and end in dark mode. My house is a 3-minute Uber ride from SaaStr. I have strong WiFi.

Been hosting a startup founder meet up at my spot for the past 2 years in September when all are in San Mateo for @saastr. Probably going to do it again. Some meet cofounders. Some meet customers. Some meet new partners. It’s laid back and fun. More details soon.

@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!

@Shalinsky @liamcode Hell yeah brother

Sweat equity 😅

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)

"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. longform.asmartbear.com/bad-advice/?ut…

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

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. 👊🏴‍☠️

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

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 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?). finance.yahoo.com/quote/TINY.V?p…

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: discretioncapital.com/articles/when-…

@awilkinson My friends have this at their house and old business. Vancouver Island built. oneofakindcw.com

I need a sauna for my place in Vancouver. What's the best sauna company that ships to Canada? Ideally fast shipping, I don't want to wait months.