Dec 15, 2025 · 51m · startup-ideas
Sahil Bloom Gives You a Plan for 2026
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gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this goal-setting episode of Where It Happens, Greg Isenberg and Sahil Bloom break down a practical seven-question Personal Annual Review framework to help listeners extract key lessons from 2025 and optimize their energy, focus, and performance for 2026.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Greg holds 33.5% of the talking time here. How this is scored →
Greg as informed peer 4.5 Guest teaching 3.0 Guest disagreement 0.0 Greg pushing back 0.2
speaking balance: gold is Greg, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:26 Nuanced disagreement on early-career autonomy
In a very collegial discussion, Sahil lightly pushes back on absolute autonomy, noting that eliminating all draining obligations is an earned privilege rather than something beginners can immediately execute.
Hardest push from Greg ▶ 16:14 Host tests boundary on privilege and saying noGreg pushes back on Sahil's advice to cut out draining people by asking if that luxury is realistic for early-career founders and 20-somethings in the zero-to-one phase.
Biggest teaching moment ▶ 13:00 Evaluating energy in the aftermath rather than the processSahil educates the host on how to evaluate energy-draining versus energy-creating tasks by focusing specifically on the post-activity physical and mental state rather than the friction felt during the act.
Greg holds their own ▶ 45:30 Host demonstrates hard-earned startup investing wisdomGreg demonstrates deep operational and angel investing expertise by breaking down a concrete multi-million dollar equity mistake and explaining why backing founder talent supersedes evaluating initial product ideas.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Greg as informed peer | Guest teaching | Guest disagreement | Greg pushing back | Why |
|---|---|---|---|---|---|---|
| Welcoming Sahil Bloom and the Power of Reflection | 3 | 3 | 0 | 0 | Greg welcomes his former co-host Sahil Bloom back to the show, setting up the 2026 planning framework. Sahil outlines the premise of reflecting on experience rather than just rushing into goal-setting. | |
| Question 1: What Did I Change My Mind On? | 4 | 2 | 0 | 0 | Sahil introduces the first question around changing one's mind as a sign of continuous reinvention. Greg agrees and adds that successful operators constantly reinvent themselves. | |
| Deconstructing Mindset Shifts and Calendar Audits | 3 | 4 | 0 | 0 | Sahil advises auditing calendar entries from the start of the year and finding what makes one cringe. Greg notes that the question is broad and requires practical tools to unpack. | |
| Categorizing Reflections: Personal, Professional, and People | 5 | 4 | 0 | 1 | Greg introduces a nuanced counterexample: activities like podcasting or workouts that drain energy in the moment but create net-positive energy afterward. Sahil explains evaluating the post-activity state rather than the in-the-moment fatigue. | |
| Managing Interpersonal Energy and Incremental Changes | 5 | 4 | 0 | 1 | Greg challenges whether cutting out energy-draining people is a luxury exclusive to established operators. Sahil concedes it is an earned privilege but argues even early-career individuals can make small, incremental adjustments. | |
| Question 3: Identifying What Drained Energy and Setting Boundaries | 5 | 3 | 0 | 0 | Both share mutual disdain for recurring meetings and Zoom fatigue, contrasting them with structured async reading memos modeled after private equity board meetings and Amazon practices. | |
| Question 4: Identifying Boat Anchors and Subtractive Progress | 4 | 3 | 0 | 0 | Sahil introduces boat anchors as subtractive friction holding people back. Greg suggests using trusted third parties or AI truth-tellers to identify these blind spots. | |
| Live AI Demonstration for Uncovering Personal Boat Anchors | 4 | 2 | 0 | 0 | Greg and Sahil run a live ChatGPT prompt to dissect boat anchors, discussing the 'strong one complex' and emotional burdens founders carry in silence. | |
| Question 5: Overcoming Fear and Reevaluating Ambition | 6 | 3 | 0 | 0 | Sahil breaks down fear as inexperience rather than incapability. Greg recounts receiving feedback from an idol that his businesses were 'not big enough,' working through the fear prompt to validate his alignment with his chosen scale. | |
| Question 6: Analyzing Greatest Hits and Worst Misses | 4 | 3 | 0 | 0 | Sahil details his greatest hit (his book launch) and the importance of being unapologetically 'all in' rather than using half-hearted effort as ego protection. Greg strongly validates this dynamic. | |
| Question 7: Core Learnings and the Value of People Over Ideas | 7 | 2 | 0 | 0 | Greg shares a major investing lesson where he passed on an exceptional founder over a flawed initial product, missing out on an eventual $3B outcome. Sahil agrees that backing talent over initial ideas is the critical differentiator. |
Statements from this episode (13)
Bloom: 'Second brain' tools create illusion of progress without actual work
“What I found in my own experience working with some of those things is that you end up moving a whole lot, but not actually making progress on things. You know, you like have this complicated productivity system, but you're not actually you know, creating prog…”
Bloom: Focus on activities providing natural pull for best life outcomes
“So the fundamental idea with both question two and question three, which we'll come to, is that your outcomes in life follow your energy. Idea being like when you are working on and leaning into things that create that lift, that natural pull, you create the b…”
Bloom: Evaluate energy drains by aftermath feelings, not during the activities
“I focus on how do I feel after rather than how do I feel during for that exact reason working out, actually the example that you brought up there is the best one in my mind for me, because there's plenty of run workouts or different lifts or whatever, where I'…”
Bloom: Leaving podcast co-host role was primarily to focus on writing
“When you and I stopped being co-hosts, like the main reason was I was going to write this book, right? I was like, I was, I'm going to take on writing as my main, main thing.”
Bloom: Cutting off unearned relationships was decade's most impactful behavioral change
“I would say if there's been one single change that has been most impactful for me over the last decade, it has been closing off my energy to people who had not earned the right to it.”
Bloom: Recurring meetings force teams to invent low-impact discussion topics
“Recurring meetings are a funny one too, because what I find happens is you create stuff to talk about on them. That's not actually impactful. You, you're like, oh, okay, I have this recurring meeting every month on the first Monday of the month. So I'm gonna h…”
Bloom: Effective boards require advance updates to focus entirely on strategy
“The structure of board meetings when well done, which was The CEO and the board and the team would send around like maybe a week in advance a deck that was basically the business update and all of the key information about the business. And then the meeting it…”
Bloom: Subtractive optimization drives progress faster than adding new routines
“Identifying what those are and cutting the line, if you will, is the fastest way to make progress. We, as ambitious, high-performing people, Automatically assume that the fastest way to make progress is to add something new. You're like, oh, okay, I'm going to…”
Bloom: Unwinding scattered commitments took a year to focus on core projects
“It led me to a fairly painful, like one full year of like unwinding a bunch of things that I had my hand in that really made no sense. I was like, why am I involved in these things to the point where now I'm Heavily concentrated in like two to three things, bu…”
Bloom: Creators must shamelessly self-promote impactful work before others share it
“If you're proud of the work that you put in and you know it's going to be impactful for the world, if you're not willing to shamelessly self-promote your thing, why should anyone else be willing to share it?”
Isenberg: Agency passed on equity in startup that later hit $3B
“One sort of miss that I had this year was I met an entrepreneur that, that I believed in. I really, really believed in. I thought he was exceptional, and I knew he was going places but he brought to me a business that I didn't believe in. So he said, hey, I'm …”
Bloom: Across 100 startup investments, winning bets backed founders over ideas
“I've probably invested in a hundred companies, but I have no, like, good frameworks. I'm not proclaiming myself to be good, but I have had a few lucky shots and the lucky shots are almost entirely because all I focused on was the founder, not the idea.”