2025-05-19 23:17:25
What does it mean to become an AI-native company?
For too many company leaders, I’ve noticed they think this means having your engineers “tab” their way through their coding tasks with a tool like Cursor, for their employees to be able to ask ChatGPT questions of their internal data, and for them to adopt AI vertical tools.
But these things, while important, are all on the surface. To become AI-native, it takes, what one company I’m lucky to work with describes as a full “metamorphosis.”
What follows is an interview I did with Borislav Nikolov, the CTO of Rekki. The transcript for our conversation was 50+ pages, so I did my best to edit for conciseness and clarity. Still, I consider Borislav as AI-native as you can get so in order not to cut some of the nuance out, I am going to publish this in two posts.
As background, Rekki has a marketplace for restaurants and their wholesale suppliers. They deal with thousands of restaurants making thousands of orders every day. This creates a stream of nitty-gritty engineering tasks to glue things together like payments, risk management, and complicated business logic. Every time the operations team had a new need or a tweak to the system, they’d create a task for the engineering team. Until one day Borislav realized: what if I can empower everyone on the team to “solve their own problems?”
I’m not sure what the company of the future looks like once AI fully permeates, but I think we all have something to learn from how Borislav approached this question.
In this post, we get into:
The “ah ha” moment of realizing that every single person in the company would soon be able to code, and how this would let him push tasks back to the domain experts in the company and have everyone “solve their own problems”.
How this changed his job as CTO from leading a team that executes on tasks to one that creates the internal infrastructure almost like a PaaS provider, where the whole company is full of developers he “can’t trust”.
His realization that if an employee can’t do something themselves, it is his fault for not giving them the right primitives.
How he pushed the behavior change internally. This started by first, having everyone in the company deeply understand large language models, and then challenging the conditioning everyone had of assuming they couldn’t solve their own problems because they couldn’t code.
In the second post, we’ll explore:
Why he still codes two days a week without any help from an LLM.
The theory of mind, and reviewing code generated by an LLM.
What the future holds as more and more code is written by LLMs.
“As they say, necessity is the mother of invention.”
Shortly after GPT 3.5 came out, Borislav, was staring down a massive backlog of engineering requests from the company’s operations team. The backlog was daunting, both in its count, and also because each task itself, while potentially trivial from an engineering perspective, required real time to ramp up on the problem before any code could even be written (let alone tested). Then it hit him: literally everyone in Rekki could now write SQL.
“So I was like, look, why can't I just enable the people that are actually asking for the tasks to do the task? If a restaurant orders three times very close together, that's probably a fraud thing. So instead of me making a system that has to check the data, has to have some state, etc., they can just do that themselves… This was the first real moment where I realized that everybody would soon be able to code and solve the tasks in whatever domain they are in.”
This was something that wasn’t possible with other no-code tools he’d tried, because inevitably the no-code platforms were not expressive enough.
“Previously what was always missing and why the low code and no code solution would fall flat was because at some point, it's just not expressive enough. Somebody has to write the code. There is this law of irreducible complexity.” But he realized that if he could give his team the right infrastructure for their code to run somewhere safely, with things like privacy considerations, security, and notifications if there is a problem, he could empower everyone in the company to code and solve their own problems.
Rather than divide the company into developers and non-developers, if everyone could write SQL, Borislav realized that the jump to building automations on a service like Zapier or Make.com was finally possible.
“Now, if we could just make this SQL into API primitive, someone can create the rest of the workflow at Zapier or Make.com, and of course the testing they can do herself by placing orders with a testing restaurant.”
So, his thought was "how can I make it possible for everyone to do their job, without me defining what they can and cannot do? What primitives are needed? How can I make it reliable and as safe as possible?”
By primitives he meant things like load/store/search, turn a SQL query into an API, or SQL query into a trigger that pushes to a webhook when there is new data, monitoring, alerting, etc.
If an employee gets stuck not being able to do something they want, Borislav considers it his fault for not giving them the right primitives.
“I almost think of myself as an internal PaaS provider, the whole company is full of developers that I cannot trust, kind of how AWS engineers think about REKKI's engineers, they have to run our code, but they don't trust any of their users, but at the same time they have to empower us giving us the right primitives to express ourselves and do what we want to do with as little friction as possible… In the future I hope I can empower everyone to use Cursor and just deploy code, but we have a long way to go to make it safe and secure.”
Depending on the company, the primitives will be different. But to Borislav, “the important part is to think of the whole company as people who can truly build anything they put their mind to, and the only limit is you, your attitude, and your infrastructure.”
“You will be surprised how much you can do with a workflow with SQL to API, ChatGPT classifier and few API calls.”
Now, rather than a company divided into developers and non-developers, the company has developers, semi-developers, and a small (~10%) non-developer make-up. Yes, the developers are still needed to unblock or enable the semi-developers to do their jobs, but that work is amortized because the developers are giving the semi-developers the “fishing rod, not the fish”.
I asked Borislav what advice he’d give other companies to make this transition from pre-AI to AI-native.
“If you put a company in front of me and I can ask them one question, it would just be ‘do you understand this technology? Can you use this machine?’” In Borislav’s experience, most people are quick to point out the AI’s limitations – hallucinations, producing bad code. But they haven’t taken the time to truly understand what the machine is and how it works.
Borislav himself studied Andrej Karpathy’s videos and others on LLMs for close to 50 hours until he could back-propagate by hand on pen and paper, and deeply understood “what a plus means and what a multiplication means and what the collapse of the vector space into a token means.” As he said, “it’s a machine we’ve never experienced.” To use it, first understand it. Once he could understand “the way the transformer programs itself to emit the token” and therefore its limitations, he understood how to take full advantage of a LLM to code, and transformed Rekki’s culture to be AI-first.
“You have to understand that by talking to it you're programming it. That's what you're doing.”
At Rekki, Borislav had the entire team watch Karaphy’s Zero to Hero series, as well as a bunch of videos from other teachers like Justin Johnson, Fei-Fei Li, and 3Blue1Brown. They did Learning Fridays where they’d watch lectures together and discuss the content.
Then, he started pushing all the requests back to the teams that had the domain expertise. His default changed from doing the tasks for people, to teaching them how to do it themselves, and making sure that they had the infrastructure that empowered them.
At first, this was hard.
“You have to believe in the capability of your non-tech people. They are conditioned to think they cannot code, to think that only engineers can not solve their technical problems. So the very first step is for you to believe in them. Then the second step is having the infrastructure to support them, and the third is to teach them to solve their problems themselves.”
For example, someone on the operations team needed to get a bunch of data. Borislav could have written a scraper for him that gets the data, parses it, and analyzes it. Instead, he told the employee to download Cursor, and just “type the request in.” “Now, he has 20 scrapers that he just uses nonstop.”
“So again, first believe that non-coders can code, then figure out where the code lives, because that is a massive problem, e.g. how do they deploy and monitor it, make.com, zapier, bolt, their own laptops etc.? And then the real issues with security, PII and GDPR, anonymization, etc. How many outages are you willing to tolerate because ChatGPT wrote a stupid infinitely recursive query?”
What Borislav demonstrates so clearly is that becoming AI-native isn't about layering AI features onto existing processes. It requires a fundamental restructuring of how we think about work, capability, and organizational design. This is the "metamorphosis" he references.
Three critical insights emerge from Rekki's transformation:
1. The democratization of technical capability is real and imminent. When everyone can code, the traditional bottlenecks between technical and non-technical teams dissolve. Rekki transformed from an engineering backlog to hundreds of automation workflows built by the people who understand the problems best.
2. Leadership roles fundamentally change. Technical leaders shift from task executors to platform builders. They create secure, reliable primitives that enable domain experts to safely solve their own problems. The parallels to cloud computing's transformation of infrastructure are striking: CTOs become an internal PaaS provider to the whole company rather than gatekeepers.
3. Organizational psychology is the biggest barrier. Both engineers who are used to being the exclusive "problem solvers" and non-technical staff who've been conditioned to believe they "can't code" must undergo significant mental shifts. The limitation isn't the technology - it's our deeply ingrained beliefs about who can do what.
The question for founders isn't whether this transformation happens, but how quickly your organizations adapt. The companies that drive this change aren't just adding AI features - they're fundamentally rethinking what it means to be an organization in the AI era.
More soon.
2025-04-30 05:02:27
Hi All -
After eight years at Benchmark, I’m shifting to a Venture Partner role. In this new role, I'll continue to make new investments on behalf of Benchmark, serve on my existing boards, and contribute to Benchmark and our portfolio. What's changing is my focus and time allocation.
When I joined Benchmark, I was drawn to its distinctive model in venture capital—a small equal partnership of no more than six general partners, all generalists, deeply committed to partnering with the most ambitious founders of our generation. With no junior people or platform team, the structure demands total dedication from each partner. It's a model that has proven remarkably successful, and also one that demands a certain approach to venture.
AI isn’t just another technology wave – it’s a transformational force that will reshape every corner of our lives. As I've watched the space evolve, I've increasingly realized that for me to best support founders building in AI, I need more space. More space to go AI-native by fully immersing myself in AI tools at the edge, more space to reflect on the last ten years and try to understand what the next ten might bring, and maybe even (don't hold me to this!) more space to think through it all by writing.
After reflecting on this with my partners, it became clear that transitioning to a Venture Partner role would give me the flexibility I need while maintaining my connection to Benchmark's core mission. I remain fully committed to Benchmark and our craft of deep partnership with the founders we back, just now with more room for curiosity and exploration (and yes… vibe coding).
For the extraordinary founders I currently work with: my commitment remains unchanged. I’m grateful for our partnership.
For founders building at the edge of AI: I'll now have more bandwidth to engage deeply with your vision. Whether you're just beginning your founder journey or scaling a team that's already found product-market fit, my email remains sarah at benchmark com.
Sarah
2025-02-03 21:45:12
James Raybould came recommended to me by multiple people when I posted about asking for AI savants, and he did not disappoint. Thank you Maisy Samuelson for the introduction!
There are so many tidbits he shared on his mindset which he describes as “AI-Forward”. I am going to include a bunch of quotes on his thinking (slightly edited for brevity). And then he shared a few fun examples on how he uses AI day-to-day.
"I just assume anything I'm doing, like almost every decision I'm making is better with AI. At this point, it's been built into almost every single thing. If I'm trying to name my team. I'm trying to write my LinkedIn post. I'm trying to write a strategy. I'm trying to think of anything I do. I go to Claude, my favorite, or my default tab is Perplexity."
"I'd say if you look at my podcast time, it's probably gone from three to five hours a week to probably one hour a week because for the other three to four hours advanced voice mode has taken over.... I think that my biggest realization is again, AI knows more about everything than we know about anything. And so therefore, why wouldn't I be curious? And so therefore if you have a choice of talking to the most knowledgeable person who has ever lived, why wouldn't I do that on just about everything?"
"I think that you and I grew up with this idea that 'Effort equals output'. I'm like, oh cool, you must have put so much time into this Sarah. Oh, what an amazing dossier you wrote. What an amazing briefing. Now we're moving to this world where the connection between effort and output is completely disappearing." To this point, James mentioned the example Ethan Mollick gives in his book Co-Intelligence on writing recommendation letters for his students. It used to be a signal when a Professor would take the time to write a recommendation letter for a student, because that effort would create scarcity. The professor isn't going to say yes to everyone who asks. What happens to the value of a recommendation letter when AI can do it in three minutes?
"I keep on reminding myself, like Ethan Mollick says, AI is the worst it will ever be today."
The three big themes for James are about 1) brainstorming and writing partner, 2) synthesizing information for him, and 3) scouring the web and other sources for information that is relevant to him (vs him having to go out and get it himself).
Three examples he gives:
"Anything, LinkedIn posts, LinkedIn long form articles, and internal stuff, like documents internally, phrasing's a lot. I find there's a lot of like, what should I call this team? What should I call this? Is there a really pithy phrase? The key there is that you ask for 25 ideas. And then say, I only like two and four. Give me 25 more. And you say, I only like one, two, and three. You just keep going.”
"Each average idea for any human is probably better than each average idea for an AI. But the AI can give you 200 of them in 10 seconds and the human can give you like 13 in like two hours. So Claude can give you 200 taglines, 150 are absolute garbage. But 50 are pretty good and 10 are magic."
He often prompts Claude after it's written something, "Let's remove the jargon and make it more like me."
James has started experimenting with OpenAI’s Operator. "It's not that each individual task is amazing. My mind was blown because I'm watching TV with with my kids, and in parallel, I'm preparing a dossier on you, and I'm finding some candidates for a search, and I'm researching our dishwasher. The average person doesn't have an EA or a Chief of Staff to give work to, but now they do."
To show how simple it was for James to get value out of Operator, here is the prompt he used:
"I'm preparing to meet Sarah Tavel from Benchmark on Monday. Can you please create a full Google document dossier style that tells me as much as you can about her. Please start with broader information and then narrow down to anything that she's written about AI on LinkedIn, X, her blog, or other public sources in the past 12 months."You can watch Operator in action here. And the output here (with some formatting from James). Definitely not perfect, but as James reminds us, “worst it will ever be.”
One of the core use cases James uses AI for is synthesizing content. A great example of this is for newsletters. Like all of us, he is subscribed to a lot of email newsletters (make this one more!), and often doesn’t read everything or know what to focus on. So he built a tool using Relay that ingests the newsletters in his Gmail, and then synthesizes the content so he gets an easy-to-glance summary every morning, and he can then dive in on the posts he’s curious about.
This use case is a classic example to me of something I’m noticing the “AI Savants” I’ve spoken to all have in common — they are willing to do the extra upfront effort to get the downstream benefits.
James kindly put together 10 slides to show how he does it here: Getting a Daily Digest of the So Whats from a Series of Newsletters using relay.app.
Here’s an example of what the output is. Check it out!!
2025-01-23 23:59:36
One thing that’s hit me lately: Google trained us all to be self-sufficient information hunters and synthesizers. When we need to diagnose a health issue, fix a coding bug, choose a vacation destination, or write a paper, we've learned to search, read, compare sources, and synthesize into personalized informed decisions or work. All the world’s knowledge at our fingertips. Better learn how to leverage it. “Let me Google that for you?” captured this ethos. How dare you ask a question that you could find or figure out yourself!
Well… thanks Google. The more I find myself taking advantage of AI, the more I realize I’ve been unlearning this trained self-sufficiency. What we all have now is an expert available to us to ask any question or even delegate many tasks. Yes, sometimes we need to give it some back-up documents, or clearer instructions, and sometimes it has no idea what it’s talking about (not that it will tell you). But if you can move from a mindset of self-sufficiency by default, to asking the LLM expert at your fingertips by default, a world starts to open.
This isn’t about moving queries off of Google into ChatGPT. It’s also a shift in the kind of problems we can tackle, and how we’d approach them:
Google Era: I’m stuck on a bug. Let me search and read a bunch of StackOverflow threads to debug this.
AI Era: Pull request to an AI developer who has access to your entire codebase.
Google Era: I wonder what diet changes or supplements I should be taking given my latest blood test results. [Does a lot of searching.]
AI Era: Uploads latest blood test result into a ChatGPT Project, “You are a medical analysis expert specializing in interpreting blood work results and creating personalized health recommendations….” [full prompt instructions here].
Google Era: I wonder how good our team is at communicating together. [Bookmarks a lot of articles on team communication to read later.]
AI Era: "Tell us something we don't know, or wouldn't want to know about ourselves" [uploads file of team Slack conversations]. (-idea and instructions from Tom Lawrence)
Google Era: My wife just did an embryo transfer. Let me search for articles on what she should be eating to maximize the changes of a healthy pregnancy.
AI Era: "You are the world’s foremost expert on maternal and pediatric nutrition like Dr. Lily Nichols. You’ve studied the nutrition studies and lore from every culture in the world that best promote maternal and baby health and brain development. Help me put together a week by week menu — breakfasts, lunches, dinner, snacks — for my wife from embryo transfer to end of fourth trimester.
My wife is a pescatarian but will do bone broths, butter, dairy, etc. She just doesn’t like eating meat, though maybe that may change with pregnancy. We have a worldly palate.” (-instructions from Aike Ho)
Are the experts perfect for every question? No, of course not. (I like how Ethan Mollick describes the “jagged frontier.”) Is this the worse they will ever be? Yes.
This isn’t just about an AI doing the work we once did of finding/synthesizing information. One thing that hits me is how much more personalized an AI result can be than a Google search will ever be. The paradigm is just so different. When I do a Google search, we all have some expectation of objectivity in the results. We critique Google when two people do the same search (e.g., on a news event) and get different results. And of course the means by which Google personalizes results has been more implicit - inferring from my searches, geo, etc. So personalization gets pushed to the edges to sites that are also stuck in a Google / search paradigm. Take TripAdvisor as an example. I have to figure out the best hotel for me by looking for clues in reviews that are relevant to me personally. Whereas with an AI, I can just tell it about my family and vacation preferences. I can store those preferences in a project, add my own reviews on hotels or trips we’ve taken, and get personalized recommendations.
This transition won't happen automatically. At least for everyone older than GenZ, self-sufficiency is deeply ingrained. Unlearning it will take conscious effort. But once you start, you realize how different the future will be. Have fun.
2025-01-17 22:02:53
For those of you looking to just get started leveraging LLMs beyond ChatGPT, this post is for you (I’ll get into more advanced tricks later!!).
My first “leverage AI” conversation was with Nathaniel Emodi, the cofounder and CEO of Highlight. Inspired by the one and only Patrick O'Shaughnessy, Nat has developed a morning routine leveraging Claude Projects that effectively functions as an AI-powered executive assistant to set his day on the right path. As he wrote:
Personally, as a busy founder I've been using Claude's Projects feature to help organize my day. I have a project called "Morning Goals" that helps unpack a long, often rambling voice memo and organize it into to-dos for myself and others; ideas for different projects; structured questions and notes for meetings coming up that day; and drafts messages for follow-up with different people.
I thought this was a great “starter” use case to write about because it’s one of those ideas that’s tangible, and once you start doing it, you start to come up with more and more ideas for how to leverage Claude or ChatGPT Projects.
For those of you unfamiliar with Claude Projects, Anthropic describes it here.
Nat’s project is “Morning Goals”.
He provided the following instructions, which Nat encourages you both to use yourself and share your feedback on if you have ideas for making it more useful:
**Morning Goals**
As a busy founder and CEO, balancing family life and the fast-paced demands of running a startup, help me organize my thoughts and drive daily productivity.
**Daily Structure**
Every morning, follow these steps:
1. Date & Overview:
Note the current date and time in [YYYY-MM-DD] format.
Record my overall sentiment: [Positive/Neutral/Negative + a brief reason].
Identify two primary focus tags reflecting key themes for the day.
2. Action Planning:
Self: Create a checklist of prioritized action items for myself.
Team: List action items delegated to others, prioritized by importance.
Carryover: Include follow-ups from previous days, noting their original date and any incomplete tasks.
3. Open Questions:
Maintain a running list of open questions I’m exploring, adding context from project documents where needed.
Identify potential people or resources to consult for insights.
4. Key Ideas & Insights:
Summarize key themes and focus areas, adding necessary context.
Propose actionable ideas, follow-up tasks, or challenges to assumptions from the perspective of a [consumer marketplace founder with 20+ years experience.]
5. Draft Communications:
Draft succinct and professional messages for different recipients, tailored to their role or relationship to the project.
Include recipient details, purpose/subject, channel (e.g., email, DM), and keep the tone casual but professional.
6. Knowledge Connections:
Identify connections between current and past notes, referencing prior entries with their date.
Highlight potential strategic implications based on these insights.
7. Outreach Opportunities:
Propose potential outreach strategies, sharing the context of why it’s relevant.
Draft message templates and outline next steps for engagement.In addition to the instructions, Nat uploaded a handful of documents to Claude’s Project Knowledge, like some Highlight strategy documents, product launch plans, revenue goals.
After dropping his kids off at school, Nat opens Claude and then does a stream-of-consciousness verbal brain dump. Claude transforms this unstructured thinking into actionable output:
Synthesizes key insights from the stream of consciousness
List of to-do’s
Drafts emails based on mentioned communication needs
Structures everything within the context of company priorities
The result? When Nat arrives at his desk ready to begin the day, he has a structured agenda that allows him to execute on his morning thoughts without the typical context-switching tax. As he described it, it’s like having an EA who not only listens to your morning thoughts but transforms them into an optimized work plan.
It’s a great simple example of how AI can bridge the gap between our natural thinking patterns and a structured productivity systems. Most productivity tools require us to adapt to their structure – here, the AI adapts to us.
Of course, this isn’t perfect yet. The output is static - you can’t check to-do’s off, or keep a running list of all the action items over past entries. And there are still times when it makes mistakes (e.g., when it surfaces prior mentioned dates, they are often wrong). But it’s clear this is just the beginning. As the models progress, Nat notes the experience will evolve from having "an experienced EA to having a Harvard MBA at your fingertips."
If you're looking to start experimenting with practical AI applications, this is an accessible entry point with immediate returns.
As always, if you're building tools in this space or have innovative approaches to AI-powered productivity, I'd love to hear from you. And for those already using similar workflows, Nat (and I!) would welcome community iteration on making it even more effective.
Note: This is part of a series exploring how the best operators are leveraging AI technologies. Stay tuned for more insights from upcoming conversations with AI innovators. And yes, a lot of this blog post was written by Claude. Except that last sentence. And this one.
2025-01-15 04:22:42
I've been thinking about my dad lately. He was a successful public equity investor, but when it came to technology, he had his ways. I remember watching him write detailed client updates on a yellow legal pad, which someone else would then type up. He preferred doing complex calculations in his head rather than learning Excel. Whenever his laptop didn't behave exactly as expected, he'd need help getting back on track.
His approach to technology makes me reflect on where we are with AI today. We're all as individuals at a similar inflection point - a moment where we can choose to stick with familiar methods or push ourselves to embrace new tools that could fundamentally change how we work.
We're already seeing a divide emerging. Some coders have become AI savants, seamlessly integrating these tools into their daily workflows. Some stick to their old ways. Those that are leaning in hard on AI are not just using AI; they're reimagining what's possible in their roles - whether they're desk workers, founders, or CEOs.
I'll admit it: I feel like I'm just scratching the surface. While I've experimented with AI tools, I know there's so much more to do. It reminds me of watching my dad stick to his yellow legal pads - there's comfort in familiar tools and methods, but also opportunity costs we might not fully appreciate until later.
So I thought it would be fun to find a way to learn from these AI pioneers. I want to understand how they're leveraging AI to enhance their productivity and creativity. What daily workflows have they transformed? What unexpected use cases have they discovered? How has it changed their approach to problem-solving?
This will be the first in (I hope!) a series of posts exploring these questions. I want to try speaking with non-coders across different roles and industries who are pushing the boundaries of what's possible with AI. My goal is to share their insights and experiences so we can all better understand how to meaningfully integrate AI into our work lives. At least that’s my goal: forgive me if this ends up being a better idea (to me at least) conceptually than in practice!!
Please consider this post an open invitation: If you're someone who has found innovative ways to use AI in your work, or if you know someone who has, I'd love to hear from you.
And as a first step: I got to enjoy the magic of dictating some rough ideas to Claude for this post, and watching it write 95% of it for me (+ create the title image).
Happy New Year!