Cracked Productivity Hacks for 2026

Founder-to-founder pro-tips on productivity hacks and I share my latest 'Productivity Stack'

Frequently Asked Questions…

In my role as the Mayor McCheese of Triangle Tweenerville, I have the pleasure of meeting 3-4 founders a week on average and events that spikes up to hundreds. In the last year the first topic that comes up has interestingly split into two buckets: (and it’s not the weather):

• Bucket 1: “I read your article on productivity and it changed my life!”

• Bucket 2: “How do you find time to do all the things you do” or the corollary: “Do you sleep?” or “Is it really you doing all this?” or “Do you have a Twin brother” and so on.

The two are a Yin/Yang of the same coin. But first let me back up. The ‘Bucket 1’ folks are referencing the Tweener Times post here that I wrote a year ago (almost) to the day. I wrote that piece because prior to writing it, the top and only first topic would 99% of the time be currently Bucket 2.

Pulling Robbie into the fun and expanding…

Robbie and I have been co-GPing (cofounders in venture-speak) and building Tweener Fund for 4+ yrs now and what’s been most fun working with him is we both are somewhat obsessive optimizers. I optimize for time and GTM. He optimizes for health and coding.

Because of the popularity of that OG post, not only are we bringing it back and making it an annual update, we’re going to dramatically expand this series and tag team it between Robbie and I:

1. In this post, I’m updating with my 2026 productivity hacks and making this an annual Tweener Tradition: founder-to-founder optimization hacks.

2. Robbie is going to share his 2026 Founder-friendly Health Hacks

3. I’m going to share what I’m learning and other Tweener Founders are using as their GTM stack

4. Finally, Robbie will wrap and share his stack that’s pushed him from a 10X coder to a 100X cracked coder.

Our goal in this series to give the founders that read this your own superpowers. Everyone knows the cliché – you can work harder or smarter, pick one. Nope, we’re saying – pick both! Work hard and smart – turn the crank on that every year by 10% and you will have a superpower – live 10yrs longer and wow, you just added 219,000 hours! Improve your productivity AND your health AND your GTM and Code.

Sound too good to be true? It isn’t buckle up and come along for the ride, here we go.

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2026 Productivity Hacks

What a difference a year makes. In 2025 I changed my productivity stack, habits and system more than any one year. This is bigger than the move from PC to Mac, bigger than Outlook to gmail, bigger than gmail to superhuman. I am now using tools in my stack that have saved me 20-60hr chunks of time. You’ve probably already guessed it, but I’ve dramatically expanded my usage of AI tools as they’ve matured, the hallucinations are down, there are new tools that are more meat and not just sizzle and they are really impacting my productivity and making my 4hr/wk // 48mins a day optimization look like child’s play. It’s so large it’s hard to quantify. I’d say it’s at least a 25% increase in productivity possibly as high some weeks that it’s over 50%. It’s allowing me to add things to my plate I never thought I’d be able to do.

Before we dive in, I want to take a baby-step back and review some foundational concept so we don’t get too far ahead of our Skis.

Quick Highlights From the OG 2025 Post

As a refresher on the OG post:

• There are a lot of great frameworks and reasons to optimize your time, the post highlighted my personal favorites.

• I love the compounding nature of doing something every year/month/quarter and how over the arc of 10-20-30 years it can feel like a super-power.

• In that compounding spirit on the topic of optimizing time, I try to find 4hrs/week or 48mins a day of optimizations over the course of a year to achieve a 10% time optimization each year.

• Thanks to compounding, with a 10%/yr improvement in just 7 years you have a 100% improvement. (confused by this math?- research the rule of 72 and compounding).

• The other part of my system I run is a commitment to research, trial if it works I’m happy to pay for a variety of tools and techniques to achieve my 48mins/day optimizations.

My (start of) 2025 Time Optimization Stack

Coders call the set of tools they use their ‘tool stack’ or devstack or simply ‘stack’ for short. In startup land we’ve started using this language to talk about the tools we use across all parts of the business. For example, in GTM we have a GTM stack and so-forth. Here’s my 2025 Time Optimization Stack back in January of 2025:

• Search engine: Perplexity

• Email: Superhuman

• Research: Gemini 1.5 DR - pubs to gdocs and ChatGPT 4o

• Note taker: Evernote

• Image creator/brianstormer: Midjourney

• Spreadsheet tool: Excel

• Presentations: PowerPoint (I’m old-school)

• Avoid: slack notifications, reddit, time suckage.

• I pointed out some vertical AIs for HR, GTM and what not - Interestingly I haven’t heard much about most of these, but I did nail the Coding tools: Cursor, Bolt, Replit, v0.

• I also pointed out some orchestration tools (Zapier/Make stand out as 2 still holding on)

What I Learned During 2025

I spent the first half of 2025 in this weird cycle:

Learn about a cool new AI tool that seems like it will help me→ Try that new tool → Give up on it after 30 days when the free period ended.

Then around June, things suddenly changed. I would try a new tool, it would be pretty good, I’d get better at using it, it would get better, it would come out with a new release and it would get better, then I’d learn to prompt it better, get better at understanding the context it needs, bet better at prompting and then I hit a breakthrough - it would change the game for me and the one new tool would unlock a huge productivity gain.

Before we get to my upgraded 2026 Productivity Stack, let’s take a look at how I work and the opportunties that presents for optimization.

How I Work and My Requirements for My Stack

I spend my time each day as both an investor and tech startup founder doing these buckets of tasks:

Investor/Tweener mode:

• Selling/persuading - Convincing founders to let us into their rounds, convincing LPs to invest in the Tweener Fund, convincing sponsors, convincing you to upgrade to a paid subscriber. …..Hey, look at this button, don’t you want to press it, aren’t you getting value? What’s 10% time improvement worth to you?

• Strategerizing - We face some interesting decisions on a regular basis on different directions we want to take the Tweenerverse with the overall mission of accelerating entrepreneurship in the Triangle. Should we do more events, should we invest in less co’s with bigger checks, what should we do next?

• Creating content - Long-form writing (Tweener Times), podcasting in audio and video (Tweener Talks), keeping LI up-to-date to raise awareness, being a guest on other pods, basically running the GTM

• Manipulating data - Using Excel and/or gsheets to manipulate lists of startups (Tweener List), portfolio companies (Tweener fund), and LPs (Tweener fund).

• Meeting people (founders and LPs) - Meeting people is simultaneously the most important thing I do, but also the hardest to optimize (analog, blocked in the 9-5 zone, synchronous and linear) and also my favorite thing. I use my extra time from optimizations to meet with more people.

Founder mode: (ReFiBuy.ai) **Note we founded ReFiBuy days after the OG post

• Selling/persuading - Persuading prospects to be customers, convincing investors to invest, convincing candidates to join.

• Strategerizing - Today’s startups face a fave of complexity - how fast can you go, how do you stay ahead of what’s sure to be a wave of ai-fueled competitors, what verticals to focus on, ICP, blasting through PMF, building GTM, sequencing of building - the list goes on, you get the idea.

• Creating content - Long-form writing (Retailgentic), podcasting in audio and video (Retailgentic pod), keeping LI up-to-date to raise awareness, being a guest on other pods, basically running the GTM inbound playbook.

• Financialing- As a pre-seed company, we can’t invest valuable capital on a financial function, so I fill in as the admin team - HR, finance, office space, etc.

• Meeting people - Meeting investors, meeting team members, meeting candidates, meeting prospects - lots of meetings.

• GTMing - Working with our GTM team to help however I can.

• Producting - Working with our Product team to work on product vision

When you fold those lists together, the opportunities for time savings are:

→ Content creation (the back-end, not the front-end writing)

→ Strategerizing (back-end)

→ Meeting setup and coordination

→ Data manipulation

→ Financialing

These are the 5 areas this past year where I focused on finding 48mins a day, 4hrs a week.

The areas in my task buckets where there’s little to no optimization (9-5, analog, synchronous, linear, fun) are: meeting people, Gtming, Producting.

I personally have put a ‘no tool zone’ around:

• The act of writing content - the words

• Persuasion

• Writing emails, messages to stakeholders (customers, investors, team, prospects, etc.

• No AI avatars attending meetings, doing content or anything like that.

I’ve met founders that have a longer list, and some have a shorter list. This is where theology comes into it. Where do you draw your line?

What are YOUR task buckets?

I wrote the above bullets in about 10 minutes - I share that because it’s not hard. Once you start, and I’ve given you a guide, it’s easy. It’s also the most important part of this system (in the OG chart I called it ‘what’s your piechart). You can’t optimize your time, unless you start by thinking about which buckets to tackle and them map those buckets to tool research. Go ahead and bang those out now and come back.

My Productivity Stack Requirements Rubrik

To earn a spot in my Productivity stack, a tool has to meet these requirements

• Multi-device – it needs to work on my laptops (Mac), phone and iPad.

• Easy to use – In the AI era UIs have taken a step back – don’t make me login 100x, make it easy to do what I need, etc.

• They must interoperate – make it easy to get data in and out, play well with others.

• Cost – While I love free, I am always willing to pay to save time, within reason. It’s always been my best investment.

• Nice to have - Multiplayer mode - if a tool is great for me, but then when the others on my team use it, we not only all enjoy the productivity boost, but the multi-player mode has a multiplying effect, shazam - that’s magic. Example: Slack has this going for it - the ultimate multiplayer tool vs. single-user tool.

My 2026 Productivity Stack

Finally without further delay, my 2026 Productivity Stack:

• Email - Day-to-day I’m still on Superhuman but in the last year they have added major AI features which have made it extremely efficient. You can read about them here.

• Email distribution - Levitate - Levitate sends emails directly from your email to people 1:1 vs. the old mailchimp style bulk send or manual. The open rates and deliverability are 100%.

• Newsletters - I use Substack (Robbie uses Beehive) - each has their pros and cons, they are both excellent.

• Podcasting - Transistor.fm on 2 pods and Libsyn on the other

• Note taker – Granola for meetings has been a huge gamechange for me and I use ChatGPT for on the fly (voice mode) for taking notes - once they added memory which has had several improvements. ChatGPT voice mode is undefeated.

• Agentic browser - I’ve tried them all and landed on Perplexity Comet - it’s agentic capabilities have improved dramatically since launch and I use it to automate many data extraction, multi-step processes and more.

• AI Virtual Assistant - I use Perplexity’s email assistant Agent for all meeting work - it’s saved me a ton of time every day coordinating, organizing and finding meeting times.

• Calendar Manager - I have 4 calendars and coordinating them has been hard to solve. Onecal has been a lifesaver. Before Perplexity’s agent came out, I used it’s calendly-like functionality for meetings, now I only use it for cal-sync.

• News monitor - I monitor social media, news venues and more for a variety of topics, companies and people - Grok excels at this.

• Writing friend - Every month I upload all of my content I’ve generated to Claude and it knows my writing style and historical content, so it’s great at brainstorming and evaluating my writing.

• Tweener List (Excel) beast mode super power - Claude for Excel has been a complete game changer for me - saving me a max of 40hrs on many complex projects that involve a ton of manipulation in Excel. I created a $50m ARR business financial model and forecast with

• Image creator/editor - I do a lot of image work and use a combination of ChatGPT and Gemini Nano Banana. Sometimes I’ll give them both the same prompt and pick my favorite. Sometimes I’ll take the output of ChatGPT and have Nano Banana make the edits, and so on.

• Multi-purpose agent - Manus - I have a lot of processes that require more than 10 steps. For those the agentic browsers can’t keep up as their context window maxes out. A lot of founders I talk to for multi-step complex agentic orchestrations use n8n or make or Zapier. I’ve tried those and they take time to setup and figure out the nuances in. Why not have an AI do that AND the orchestration - that’s where Manus come in - I give it some pretty complex steps with a ton of context and files and it thinks and thinks and ‘bing’ it’s done.

• Presentation Inspo - I’ve tried Gamma (Robbie’s favorite), but I prefer Manus - it comes up with some outrageously good ideas - it always improves on my slides.

• Distribution to socials - Buffer

• Viral clips - OpusClips

Putting it All together: Applying my Productivity Stack to my Task Buckets

Earlier I mentioned my ‘Task Buckets’ another way to think about my Productivity Stack is which tools I pull out for each of my task buckets. Here’s that view:

Content Creation:

• Claude for Inspo

• Substack for mass distribution of written content

• ChatGPT and NB for images

• Levitate for 1:1 tight-beam content

• Transistor/Libsyn -

• Buffer - distributing content to socials

• Opusclips - viral clips

Stragerizing:

• ChatGPT and Claude for brainstormin’

• Granola - review call transcripts individually and across co

• Manus for presentations (with support in images by ChatGPT/NB)

Meetings:

• Perplexity Agent - meeting organization

• OneCal - calendar synchronization

Data Manipulation:

• Manus in partnership with Claude for Excel

Financialing:

• Claude for Excel

• Manus if needed

Day-to-day:

• Superhuman for email

• Perplexity Comet for 1-5 step items

• Grok for information monitoring and consumption

What Did YOU Learn Last year? Plus… Up Next…

I hope you enjoyed this year’s update on my productivity hacks and it helps you achieve even better results. Looking forward to 2026, if I can optimize half as much as I did in 2025, I’ll be very happy. I don’t know right now if this was a once-in-a-lifetime surge or if, thanks to AI, we’re on a new curve. Check in this time next year in Jan 2027, you’ll be able to come back where I’ll share how and what I did in 2026.

Let everyone know any productivity hacks, tools or tips you recommend or learned in the last year in the comments and I’ll add them to the mix in 26.

Up next, Robbie will tag in and share his health optimization hacks next week.