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Doug Regner
@DougRegner
I help early-stage founders find PMF and build a successful go-to-market motion. Operating Partner at @Unusual_VC.
Salt Lake City, UT
Joined November 2009
684 Following
600 Followers
1.9K Posts
@thogge You must look at Unicorn exits to really move the needle in Utah's direction
@samdblond It’s true. It still works and few do anything like it.
The kids after he did the red-tailed hawk sound
Relationships continue to matter. Maybe more so than ever!
The Three Humans Left in a VC Firm
Fred Wilson, co-founder, Union Square Ventures, interviewed by Michael Mignano (USV)
[I post one executive summary daily of an interview I enjoyed and learnt from. I loved this interview that @mignano did with @fredwilson, who I've learnt a tremendous amount from on the board of Coinbase. Tons of great nuggets for founders and investors.]
Summary: After 40 years in venture, Wilson has rebuilt USV around a single conviction. Only three things in the firm still need a human: picking the thesis, building relationships with founders working in that thesis, and supporting them after the check. Everything else, including sourcing, diligence, term sheets, and CRM, is being handed to agents. The interview is a working sketch of what a venture firm looks like when the back half of its job becomes software, and a clear read on what stays human-only and why.
1. The Three Humans Left. A year ago Wilson wrote a memo to his partners saying that if he were starting USV from scratch today, only three jobs would stay with humans: high-level thesis development, building relationships with founders inside that thesis, and supporting them after the check. Everything else gets handed to agents. USV is now executing on that memo, not theorizing about it. For founders raising, this is the new operating profile of the firm sitting across the table.
2. Agents Love Data Rooms. "I hate data rooms. Agents love data rooms." USV no longer asks a junior associate to scrub the data room before a term sheet. An agent reads the room and answers questions in conversation: cap table, vesting, founder ownership, anything in the corpus. The effect on partner time is direct, with less work on the parts of the job no one enjoys and more time with founders.
3. Term Sheets Without Lawyers. USV's term sheets are now written by an agent, with no outside counsel stamp at the term-sheet stage. The firm seeded the agent with standard term sheets by sector and by stage, then partners shape each document in conversation with the agent. Wilson does not yet trust an agent to write long-form definitive docs. The implication for founders: term sheets land faster, with less round-trip friction, and the cost structure of the next-generation venture firm starts to drop.
4. The Kill Zone Test. Wilson ran a sample contract through a legal-AI startup and through raw Claude Code, side by side, and Claude's markup was better. "All of legal AI is in the kill zone." The test is portable to almost any AI vendor pitch. If a wrapper company cannot outperform the raw model on the thing it sells, the wrapper is paying for the privilege of being disrupted. Operators should run the same test before signing a multi-year contract.
5. No Wrappers Allowed. To survive the kill zone you cannot wrap a model. You have to rebuild the business model from scratch around the new economics. Cursor is the example Wilson reaches for: it has been hugely successful, but more developers are dropping back to raw Claude Code, and nothing stops Anthropic from shipping an IDE. A defensible AI company redesigns the workflow itself, so the foundation lab would have to abandon its current pricing model to copy.
6. Energy Is the AI Trade. About a third of USV's deployment now goes to energy, because no matter which model wins, the winner needs power. The firm has backed a decentralized model-training network and a company that turns each grid-scale solar and wind plant into a mini data center selling inference tokens. The trade is indexed to AI without forcing USV to pick the model. Builders hunting for a less crowded adjacent market should read the same memo, because the picks and shovels of AI run through electricity.
7. Sellers, Not Coders. The skill USV now overweights in founders is selling: recruiting, fundraising, convincing customers, inspiring teams. Forty years has taught Wilson that the founder who can tell the story and bring it to life wins more often than the founder who can write the code. The corollary is uncomfortable for technical founders. "Actually being able to write code is probably not a big deal anymore," though enough technical vision to see three moves ahead still matters. If you are a CEO who cannot recruit, that is now your constraint.
8. The 80–90% Open Source Window. Open-source models, especially the ones shipping out of Asia, are running at 80 to 90 percent of the quality of the closed frontier models. Right now the closed labs are subsidizing usage, so price does not force the comparison. When the labs have to charge a real margin, open source becomes a serious value alternative and the playing field levels. Wilson is not betting the firm on this outcome, but he is hedging into the quadrant where open source wins.
9. Founders Still Want Humans. Founders do not want to raise money from an agent. They want to know the human they are getting in business with, and that is why Wilson does not see VC automating itself out of a job in the short term. The firm can automate the back half of the workflow. The front half, sitting across from a founder at 11 p.m. when they have had a horrible day, stays human.
10. Don't Pass on Price. The biggest regrets of Wilson's career are deals he passed on because the price was too high. The market-clearing valuation will almost always feel uncomfortable a year later, and the right answer is to find a way in, even if that means buying secondary instead of leading the round. Saying no on price is a defensive move masquerading as discipline. Founders raising can use the line in negotiation, because a firm that walks on price is telling you it has not adjusted to the current market.
11. Offense Over Defense. Wilson lost $25 million in six months in 2001 and learned that getting it wrong is a byproduct of the job, not a verdict on the investor. He spent his first 15 years scared of losing money and only got good at venture once he stopped playing defense. The advice is harder to apply for someone breaking in, because the first checks really do matter, but the directive holds at every level. For operators, the analog is the founder who refuses to ship until the product is perfect, because you cannot win a game you are not playing.
12. The Relationship Is the Moat. After 40 years and an AI rebuild of the firm, Wilson's one-line summary of the venture business is the same as it was on day one. The relationship between the investor and the founder is the secret sauce. Everything else, including the work USV used to staff up to do, gets compressed by technology. Find great founders, build real relationships with them, and help them build great companies. If your venture pitch to LPs does not lead with that, you are pitching the wrong business.
The Three Humans Left in a VC Firm
Fred Wilson, co-founder, Union Square Ventures, interviewed by Michael Mignano (USV)
[I post one executive summary daily of an interview I enjoyed and learnt from. I loved this interview that @mignano did with @fredwilson, who I've learnt a tremendous amount from on the board of Coinbase. Tons of great nuggets for founders and investors.]
Summary: After 40 years in venture, Wilson has rebuilt USV around a single conviction. Only three things in the firm still need a human: picking the thesis, building relationships with founders working in that thesis, and supporting them after the check. Everything else, including sourcing, diligence, term sheets, and CRM, is being handed to agents. The interview is a working sketch of what a venture firm looks like when the back half of its job becomes software, and a clear read on what stays human-only and why.
1. The Three Humans Left. A year ago Wilson wrote a memo to his partners saying that if he were starting USV from scratch today, only three jobs would stay with humans: high-level thesis development, building relationships with founders inside that thesis, and supporting them after the check. Everything else gets handed to agents. USV is now executing on that memo, not theorizing about it. For founders raising, this is the new operating profile of the firm sitting across the table.
2. Agents Love Data Rooms. "I hate data rooms. Agents love data rooms." USV no longer asks a junior associate to scrub the data room before a term sheet. An agent reads the room and answers questions in conversation: cap table, vesting, founder ownership, anything in the corpus. The effect on partner time is direct, with less work on the parts of the job no one enjoys and more time with founders.
3. Term Sheets Without Lawyers. USV's term sheets are now written by an agent, with no outside counsel stamp at the term-sheet stage. The firm seeded the agent with standard term sheets by sector and by stage, then partners shape each document in conversation with the agent. Wilson does not yet trust an agent to write long-form definitive docs. The implication for founders: term sheets land faster, with less round-trip friction, and the cost structure of the next-generation venture firm starts to drop.
4. The Kill Zone Test. Wilson ran a sample contract through a legal-AI startup and through raw Claude Code, side by side, and Claude's markup was better. "All of legal AI is in the kill zone." The test is portable to almost any AI vendor pitch. If a wrapper company cannot outperform the raw model on the thing it sells, the wrapper is paying for the privilege of being disrupted. Operators should run the same test before signing a multi-year contract.
5. No Wrappers Allowed. To survive the kill zone you cannot wrap a model. You have to rebuild the business model from scratch around the new economics. Cursor is the example Wilson reaches for: it has been hugely successful, but more developers are dropping back to raw Claude Code, and nothing stops Anthropic from shipping an IDE. A defensible AI company redesigns the workflow itself, so the foundation lab would have to abandon its current pricing model to copy.
6. Energy Is the AI Trade. About a third of USV's deployment now goes to energy, because no matter which model wins, the winner needs power. The firm has backed a decentralized model-training network and a company that turns each grid-scale solar and wind plant into a mini data center selling inference tokens. The trade is indexed to AI without forcing USV to pick the model. Builders hunting for a less crowded adjacent market should read the same memo, because the picks and shovels of AI run through electricity.
7. Sellers, Not Coders. The skill USV now overweights in founders is selling: recruiting, fundraising, convincing customers, inspiring teams. Forty years has taught Wilson that the founder who can tell the story and bring it to life wins more often than the founder who can write the code. The corollary is uncomfortable for technical founders. "Actually being able to write code is probably not a big deal anymore," though enough technical vision to see three moves ahead still matters. If you are a CEO who cannot recruit, that is now your constraint.
8. The 80–90% Open Source Window. Open-source models, especially the ones shipping out of Asia, are running at 80 to 90 percent of the quality of the closed frontier models. Right now the closed labs are subsidizing usage, so price does not force the comparison. When the labs have to charge a real margin, open source becomes a serious value alternative and the playing field levels. Wilson is not betting the firm on this outcome, but he is hedging into the quadrant where open source wins.
9. Founders Still Want Humans. Founders do not want to raise money from an agent. They want to know the human they are getting in business with, and that is why Wilson does not see VC automating itself out of a job in the short term. The firm can automate the back half of the workflow. The front half, sitting across from a founder at 11 p.m. when they have had a horrible day, stays human.
10. Don't Pass on Price. The biggest regrets of Wilson's career are deals he passed on because the price was too high. The market-clearing valuation will almost always feel uncomfortable a year later, and the right answer is to find a way in, even if that means buying secondary instead of leading the round. Saying no on price is a defensive move masquerading as discipline. Founders raising can use the line in negotiation, because a firm that walks on price is telling you it has not adjusted to the current market.
11. Offense Over Defense. Wilson lost $25 million in six months in 2001 and learned that getting it wrong is a byproduct of the job, not a verdict on the investor. He spent his first 15 years scared of losing money and only got good at venture once he stopped playing defense. The advice is harder to apply for someone breaking in, because the first checks really do matter, but the directive holds at every level. For operators, the analog is the founder who refuses to ship until the product is perfect, because you cannot win a game you are not playing.
12. The Relationship Is the Moat. After 40 years and an AI rebuild of the firm, Wilson's one-line summary of the venture business is the same as it was on day one. The relationship between the investor and the founder is the secret sauce. Everything else, including the work USV used to staff up to do, gets compressed by technology. Find great founders, build real relationships with them, and help them build great companies. If your venture pitch to LPs does not lead with that, you are pitching the wrong business.
@dGod23 Spit out my coffee
@boxcardavid @westmagco @a16z @foundersfund @LuxCapital @MenloVentures Exciting to see more robotics components being made domestically!
Utah continues to make moves
We have a real shot at bringing @MLB to the Beehive State.
Utah has the momentum, the vision, and leaders like the Miller family helping rally support behind a team Utah can call its own.
More here: https://t.co/BKHg74T1yX
@BobbyBizScout Will be fun to watch how this plays out!
It’s only called Stratocaster if it’s from the Stratocaster region of the USA. Otherwise it’s sparkling guitar
Death by 1,000 cuts
One of California’s largest insurers will hike rates nearly 30% this fall https://t.co/djdjHRzAfn via @sfchronicle
— THE FRONT-LINERS
In a world that will become saturated with AI communication, the human touch will matter more than anything to customers. This is a bottleneck that you shouldn't replace - even when agents are high enough quality to do video meetings. One-on-one meeting time with customers is something that shouldn't be automated. The systems around the meetings should be - so that front-liners spend nearly 100% of their time with customers.
Today we reduced headcount by 22%. The business is the strongest it's ever been. So I think it's important to be direct about what I'm seeing and why.
First, I made this decision and I own it. I did it because the way to operate at the highest level of productivity is changing, and to win the future, ClickUp needs to change with it.
Second, this wasn't about cutting costs. Most savings from this change will flow directly back into the people who stay. We'll be introducing million-dollar salary bands. If you create outsized impact using AI, you'll be paid outside of traditional bands.
Most importantly, I have the deepest gratitude for those affected. We're doing this from a position of strength specifically so we can take care of people properly. Everyone affected receives a package aimed at honoring their contributions and easing the transition.
I only see two options: wait for this to play out gradually in the market or be honest about what I'm seeing and act proactively.
THE 100X ORGANIZATION
The primary change is that we're restructuring around what I call 100x org. The goal is 100x output. The roles required to build at the highest level are fundamentally different than they were a year ago.
Incremental improvements to existing systems won't get us there. We need new ones. That means creating enough disruption to rebuild rather than iterate on what's already broken.
The common narrative is that AI makes everyone more productive. It doesn't. Many of the workflows of today, if left unchanged, create bottlenecks in AI systems.
These roles will evolve. But waiting for that to happen naturally means falling behind now.
The 100x org is actually heavily dependent on people - infinitely more than today. This is only possible with 10x people that have embraced and adopted new ways of working.
THE BUILDERS, AGENT MANAGERS, AND FRONT-LINERS
— THE BUILDERS: 10X ENGINEERS
I don't think most companies have internalized what's actually happening with AI in engineering. The common narrative is that AI makes all engineers more productive. That may be true in isolation, but at an organization level - that is the farthest thing from reality.
Here's what we've validated recently at ClickUp: the great engineers, the ones who can orchestrate, architect, and review, are becoming 100x engineers. They're not writing code. They're directing agents that write code. The skill is judgment.
AI makes the best engineers wildly more productive, and everyone else using AI slows these engineers down.
Think about it - the bottlenecks are (1) orchestration - telling AI what to do, and (2) reviewing - what AI did. Everything is leapfrogged and no longer needed.
So who do you want orchestrating and reviewing code?
And how do you want your best engineers to spend their time?
If your best engineers are spending time reviewing other people's code, then this is inherently an inefficient bottleneck. These engineers can review their agent's code much faster than reviewing human code.
The new world is about enabling your 10x engineers to become 100x.
The wrong strategy is to push every engineer to use infinite tokens. Companies doing this are celebrating 500% more pull requests. But customer outcomes don't match the volume of code being generated.
I call this the great reckoning of AI coding, and every company will face this soon if not already.
More code is just another bottleneck to the best engineers, and ultimately to your company's impact as well.
— THE BUILDERS: 10X PRODUCT MANAGERS
Product management and design roles are merging.
Designers that have customer focus, become more like product managers.
And product managers that have intuition for UX become more like designers.
The bottleneck of user research is gone. It takes us just one mention of an agent to kickoff research and analyze results.
The bottleneck of product <> design iteration is also gone. The product builder iterates on their own, along with agents and skills that ensure alignment with quality and strategy.
Also controversial today - I believe that the wrong strategy is to have your PMs shipping code - that just introduces another bottleneck that the best engineers will waste their time on.
To be clear, PMs should be coding but they should do this in a playground to iterate, validate, and scope. That code should not go to production.
Everything outside of managing systems, orchestrating AI, and reviewing output becomes a bottleneck.
That's why the other roles that are critical along with these are the systems managers (to reduce bottlenecks) along with a bottleneck you can't replace - customer meeting time.
— THE SYSTEM MANAGERS
Ironically, the people that automate their jobs with AI will always have a job. They become owners of the AI systems - agent managers. We have many examples of these people at ClickUp.
The underlying systems in which we operate are absolutely critical to get right. I think most companies are delusional to think they can iterate on existing systems and compete in this new world.
You must create enough disruption so that old systems are deprecated entirely. If there's any definition for 'AI native' that's what it is.
— THE FRONT-LINERS
In a world that will become saturated with AI communication, the human touch will matter more than anything to customers.
This is a bottleneck that you shouldn't replace - even when agents are high enough quality to do video meetings.
One-on-one meeting time with customers is something that shouldn't be automated. The systems around the meetings should be - so that front-liners spend nearly 100% of their time with customers.
REWARDING 100X IMPACT
In a world where companies are able to do so much more with less, where does that excess money go?
In our case, much of the savings in this new operating model will flow directly back to those that enabled it.
We must reward people that create productivity accordingly. This aligns incentives on both sides. Plus, in a world where your best people create 100x impact, you can't afford to lose them.
You should aim to retain these employees for decades. The context they have and their ability to efficiently orchestrate and review will be nearly impossible to replace.
Compensation bands of today should be thrown out the door. We're introducing $1 million cash/year salary bands with a path available to nearly everyone in the company if they produce 100x impact by creating or managing AI systems.
THE FUTURE
Nearly every company will make changes like these. The ones that do it proactively will define what comes next.
The future is not fewer people. It's different work, new roles, and better rewards for those who embrace it. We're already seeing entirely new roles emerge, like Agent Managers, that didn't exist a year ago.
ClickUp is positioning to lead this shift, not just internally, but for our customers too. I've never been more certain about where we're headed.
Today is a big day for @SocketSecurity. We just raised a $60M Series C at a $1B valuation, led by @ThriveCapital with participation from @a16z, @AbstractVC, and @CapitalOne Ventures. Total funding is now $125M.
Four years ago, we started Socket because open source dependencies were flowing into production faster than anyone could vet them. AI has massively accelerated that. Code is being written, shipped, and deployed before any human reads it. Security has to operate at that same speed.
One data point from Thrive's diligence that I keep coming back to: they first discovered Socket because @cursor_ai, @OpenAI, and @AnthropicAI all independently told them it was the most important security tool they'd adopted for AI-driven development. Three of the most sophisticated AI companies converging on the same vendor unprompted.
Since our Series B, Socket has grown to more than 20,000 organizations, protecting over 1.5 million repositories and blocking more than 1,000 supply chain attacks every week. The team is now over 100 people.
Three out of five FAANG companies are Socket customers. So are the companies building the most ambitious AI products: @AnthropicAI, @cursor_ai, @xai, @figma, @vercel, @Replit, @scale_AI, @GustoHQ, @Mercadolibre, and @cribl_io, alongside Fortune 100s in financial services and global media.
What we've shipped since the last round:
• Socket Firewall blocks malicious packages at install time, before they reach a developer's laptop or CI pipeline. Free for everyone.
• Reachability analysis via our acquisition of Coana, eliminating 50-80% of irrelevant vulnerability alerts by focusing only on CVEs that are actually exploitable.
• Socket Certified Patches for remediating exploitable CVEs in seconds without waiting on upstream maintainers.
• Coverage extending to browser extensions, editor extensions, MCP servers, and AI tools via our acquisition of @secureannex.
When the Axios compromise hit, our detection systems flagged the malicious dependency within six minutes. Within 24 hours, more than 2,000 organizations onboarded to Socket to block it.
Where the funding goes: deeper investment in Firewall, massively expanding Certified Patches, moving protection closer to every point of install across the developer toolchain, and new product launches pushing Socket into a category we haven't entered before.
We're hiring across engineering, sales, customer success, and threat intel.
❤️ Thank you to our customers, investors, and the open-source community for your support. Together, we’re making software safer for everyone.
Meet the next wave of robotics startups. 🤖
The AWS x @MassRobotics Fellowship cohort is advancing real-world robotics across agriculture, manufacturing, humanoids and beyond.
From autonomous farming to AI-driven automation, #NVIDIAInception members @burro_ai, @config_inc, Deltia, @HaplyRobotics, Luminous Robotics, @roboto_ai, Telexistence, Terra Robotics, and WiRobotics are shaping the future of physical AI. 📖 https://t.co/0ElNEbdg45
#NationalRoboticsWeek
Excited for this one!
🚀Introducing Motus, the open-source agent infrastructure that learns in production.
Existing agent infra serves static agents: the harness, model, and workflow are fixed after deployment. But static agents degrade over time. The harness goes stale, new models go unincorporated, context drifts, and latency compounds.
Motus closes this gap by learning from every trace (failures, latency, cost, and task outcomes) and using those signals to continuously optimize agent harness, model orchestration, context memory, and end-to-end latency.
Early results: higher accuracy than any single frontier model at 2.3× lower cost (Terminal-Bench 2.0, SWE-bench Verified), with 52% lower latency and 45% better memory recall.
Open source under Apache 2.0. Works with any agent SDK. Deploy with one command.
https://t.co/C4u6JUzige
https://t.co/QIfKIikZQb
I think my Tesla GPS might be be a little off!
We’re excited to lead the $6.3M seed round in @MiravoiceAI, a specialized AI voice agent platform transforming how research and operations teams collect structured data through voice.
We couldn’t be more thrilled to partner with @najain, @2Shreyz, and Danny as they build what’s next.
https://t.co/DO42auks2S
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