Episode 53 of The Security Podcast of Silicon Valley aired on September 1, 2024, with Jon McLachlan hosting alone. The guest was Lorenzo Thione, whom the show notes called “a philanthropist, LGBTQ advocate, and investor,” the co-founder and chairman of StartOut and the managing director of Gaingels (Podbean). Jon opened with a question.
“So share with us, do you think of yourself as a security person?”
Jon McLachlan, at 0:38
The answer was no, and the next forty-five minutes showed why that didn’t matter. Lorenzo co-founded Powerset, a natural language search engine that Microsoft bought in 2008, and he invests in AI for a living. His worry and his thesis are the same thing: AI makes old attacks cheaper and invents new ones, so somebody has to build the defenses.
The conversation was recorded in April 2024. The tape fits that date: Jon speaks of Peacemakr in the past tense, “when I was founder and CEO of Peacemakr,” and his LinkedIn has Peacemakr ending in October 2023 (LinkedIn).
This page is the rest of it: a section for each part of the conversation with the sources beside it, fifteen figures, nineteen clips from the tape, the full transcript, and five tools: a quiz, a scorecard for whether a cloned voice would get money out of your company, a calculator for what a 1% pledge is worth, a timeline from 1938 to 2026, and a to-do list.
A note before the sections. Lorenzo told the story of the call to Congress from memory, and he said so, so the page sets it beside the testimony on the record. And when he and Jon talk numbers, the 1% and the 10% are theirs, and the rest of the calculator is our example.
Not specifically a security person
Lorenzo answered the opening question straight.
“So no, not specifically. I do not consider myself a security person.”
Lorenzo Thione, at 0:43
“I guess my security knowledge stems from a good enough education in computer science.”
Lorenzo Thione, at 0:47
That education is a master’s degree in software engineering from the University of Texas at Austin, by Wikipedia’s account of Powerset’s founders, and before Powerset he worked on natural language processing at FXPAL (Wikipedia). FXPAL, the FX Palo Alto Laboratory, was a research lab for Fuji Xerox, with AI among its three main research areas (Wikipedia). He said the security courses were eye-opening, and then he said what really holds his attention.
“artificial intelligence in its most current and advanced forms represents both an opportunity to improve our security as well as a risk of seeing more surfaces of attack and more sophisticated ways in which these can be breached.”
Lorenzo Thione, at 1:11
He named three reasons the risk side is growing, all in one breath.
“Because with very advanced technical models being open sourced and available, with computational costs significantly going down, with the wide accessibility of data, both on the open web as on the dark web, you actually start to really run the risk of being completely unprepared if all you have is the traditional ways of protecting yourself from cyber threats.”
Lorenzo Thione, at 1:29
Open-source AI, as the Open Source Initiative defines it, is an AI system anyone can use, study, modify and share, including its data, code and model parameters (Wikipedia). The dark web is web content on darknets that need specific software, configuration or authorization to reach (Wikipedia). Put the three together and an attacker who once needed a lab now needs a laptop, a public model and whatever the target has already posted.
What I have defined or called containment
Lorenzo isn’t only watching this. He invests in it.
“And one of the areas that I focus on is what I have defined or called containment.”
Lorenzo Thione, at 2:02
He said the idea is broader than cybersecurity, and he split it in two. On one side, AI makes the old problems worse.
“And what you have is, on one hand, the exacerbation of the seriousness and the risks that existed, anything from fraud to cyber intrusion to data security issues.”
Lorenzo Thione, at 2:20
On the other, it makes new ones.
“At the other end of the spectrum, you have completely new problems that are created by these technologies, including things like proper copyright attribution, detection of misinformation.”
Lorenzo Thione, at 2:34
And the two sides meet in the middle, at the deep fake.
“when you get like deep fake detection issues, you also are acting against the potential of those fakes being used for fraud or for other types of social engineering and so on.”
Lorenzo Thione, at 2:49
Deepfakes are images, videos or audio edited or generated with AI tools or editing software, a form of synthetic media (Wikipedia). Misinformation is incorrect or misleading information, spread with or without intent (Wikipedia), and copyright is the owner’s exclusive right to copy, distribute, adapt, display and perform a creative work (Wikipedia). Social engineering, in security, is the use of psychological pressure to get people to act or to give up confidential information, and phishing is one kind of it (Wikipedia).
Are you sure that it’s actually your best friend?
Jon had a specific scenario in mind, from something Lorenzo had shared.
“Actually, one of the things that you posted on LinkedIn really grabbed my attention.”
Jon McLachlan, at 3:34
The post was the phone call. Your best friend calls, you pick up, and it’s their voice.
“And actually, are you sure that it’s actually your best friend that you’re talking to?”
Jon McLachlan, at 3:48
Audio deepfake technology, also called voice cloning, is AI that generates speech convincingly mimicking a specific person, often saying things they never said, and it has drawn criticism for its use in scams, phishing and misinformation (Wikipedia). Voice phishing, or vishing, is phishing over the phone (Wikipedia). Lorenzo didn’t treat it as a thought experiment.
“I wish that were a scenario that was sci-fi and made up and far from being possible.”
Lorenzo Thione, at 3:55
“The reality is that we are dealing as a society with these advanced types of scams and social engineering and otherwise already.”
Lorenzo Thione, at 4:01
A politician was actually testifying to Congress
Lorenzo reached for a story he’d heard.
“In fact, I can’t remember the name, but a politician was actually testifying to Congress”
Lorenzo Thione, at 4:08
In his telling, the man had just been in a minor car crash, which already had him on edge, and then the call came.
“and got a call from his son saying that he was in prison, I think, or something, and needed money to be sent to some address or whatever it is.”
Lorenzo Thione, at 4:43
The man saw through it, as Lorenzo remembered, but the point was how it felt.
“because all of your defenses go down when your primordial brain, the one that acts on instincts and really fast to react, is getting all of these signals that say, this is your son.”
Lorenzo Thione, at 5:12
“They speak with the same affectation, and they’re saying things that theoretically could be true.”
Lorenzo Thione, at 5:26
“So your defenses completely go down, and you become much less rational and much less sort of wise to those risks.”
Lorenzo Thione, at 5:31
Congress has heard a call like that. On November 16, 2023, the Senate Special Committee on Aging held a hearing titled “Modern Scams: How Scammers Are Using Artificial Intelligence and How We Can Fight Back.” One witness, Gary Schildhorn, a Philadelphia attorney, described a call in his son’s voice saying he’d been in an accident, had hit a car driven by a pregnant woman and been arrested, and then a caller posing as a lawyer said bail was $90,000 and asked for 10 percent, $9,000. Then his real son reached him on FaceTime and told him he was being scammed (govinfo). Lorenzo remembered a politician and a crash on the father’s side, so the record may not be the story he had in mind. It is the same call.
The truth lies somewhere in the middle
Lorenzo turned the story into a question about the technology itself.
“the question becomes to what extent technology is the culprit, and to what extent are we as a society kind of losing track of the true balance of benefit and costs that any new transformational technology really brings.”
Lorenzo Thione, at 5:46
He thinks people overweight the dangers and underweight the long-term benefits, and that both camps in the AI argument go too far. One side is the doomsday camp, which wants to keep models closed. The other side swings the opposite way.
“But at the other end, really, also, there’s a risk of being far too Pollyannish”
Lorenzo Thione, at 6:38
“There’s no, let’s just keep going as fast as we can with no guardrails in developing these technologies.”
Lorenzo Thione, at 6:55
The page’s title is his answer.
“And as it always happens, I think, in life, it’s a good lesson to be learned, that the truth lies somewhere in the middle.”
Lorenzo Thione, at 7:02
“And we should be walking in this with open eyes.”
Lorenzo Thione, at 7:09
Good cops against the thieves and robbers
The middle isn’t standing still. Lorenzo’s middle is a spending plan.
“I think the right thing to do is to invest in new technologies and in advanced methods to fight against these misuse or even the side effects of these.”
Lorenzo Thione, at 7:34
“Some people call it an arms race, and to some extent it is, but that’s the story of humanity and of its technological progress.”
Lorenzo Thione, at 7:45
An arms race is a competition between states for superior armed forces and military technology, and unlike a sporting race it has no finish line, it spirals on (Wikipedia). Lorenzo’s examples ran from the invention of currency through industrialization and the internet to cryptocurrency, every one of them used for fraud. His conclusion:
“Instead of constraining the technology, we need to invest in figuring out how to have good cops against the thieves and robbers and fraudsters that want to manipulate that technology for their own gain.”
Lorenzo Thione, at 8:05
99.9999% of people in this world are good
Jon agreed, and started from people rather than tools.
“I think of technology as a tool.”
Jon McLachlan, at 8:20
“It turns out that I believe wholeheartedly that 99.9999% of people in this world are good”
Jon McLachlan, at 8:23
Then he did the arithmetic the other way. A tiny fraction of people will push the big red button, so there are evil people in the world.
“It is itself not inherently good. It is itself not inherently bad. It is how we use it that matters.”
Jon McLachlan, at 8:59
He blamed the panic on wiring older than the technology.
“So when the bush moves, it must be a lion, so we run.”
Jon McLachlan, at 9:28
The “lizard brain” is the popular name for the reptilian complex in the triune brain, Paul MacLean’s 1960s model of the brain, which Wikipedia calls a once popular model (Wikipedia). Jon’s point doesn’t need the model. Fear that fires first kept our ancestors alive, and it fires the same way at a new technology.
“But we still have to deal with the edge cases, I would say, of that, that there are evil people in the world, and hence security, right?”
Jon McLachlan, at 10:05
You can’t trust the voice on the phone anymore
Jon came back to the call.
“Someone calls you up, and all of a sudden you hear a trusted voice, but it’s not who you think it is. You can’t trust the voice on the phone anymore.”
Jon McLachlan, at 10:26
He compared it to the little lock icon people were taught to look for before typing a password into a website, and wondered whether calls would get a habit like that. Lorenzo wasn’t sure the lock icon had worked either.
“I wish the majority of people even knew how to look for the lock icon and stay away from phishing websites and otherwise.”
Lorenzo Thione, at 10:47
“I think that technology companies have done a lot to try and guard for the ignorance or the naivete of users, and helped.”
Lorenzo Thione, at 10:55
Phishing is a form of social engineering in which attackers trick people into giving up sensitive information or installing malware, and Wikipedia notes that large language models can now automate personalized phishing at low cost (Wikipedia).
Make sure you have passwords and shared secrets
Then Lorenzo gave the most useful advice in the episode. He said that until about two years before, the cloned-voice scenario would have seemed far-fetched, and now it’s real, so he tells people to stop trusting their senses.
“just stop relying on what you see and what you hear, or rather the characteristics of what you see and what you hear”
Lorenzo Thione, at 11:20
“much like we do with security and passwords, on knowledge, right?”
Lorenzo Thione, at 11:29
“And the one thing that is still going to be difficult is for someone who’s not supposed to have certain knowledge to display it, to show it, to give it to you.”
Lorenzo Thione, at 11:33
“make sure you have passwords and shared secrets that you don’t discuss with anyone else and that you can use in very critical situations to basically make sure that the other person knows it’s actually really you.”
Lorenzo Thione, at 11:50
That’s an old idea from cryptography pointed at a new problem. A shared secret is a piece of data known only to the parties involved, and it can be a PIN, a password or a passphrase (Wikipedia). Static knowledge-based authentication is built on a pre-agreed set of shared secrets (Wikipedia). And in the language of NIST’s digital identity guidelines, the person proving who they are is the claimant and the person checking is the verifier (Wikipedia). On a cloned call, you’re the verifier, and a voice is not a secret.
A few practical points of ours, not Lorenzo’s. Agree on the phrase in person, never in a text or an email a scammer could read. Don’t make it anything findable, like a pet’s name or a school. When a call asks for money, end it and call back on a number you already had. At work, the same rule belongs on any request to move money or change bank details.
Angels with a hard G
Jon moved on to Gaingels and checked the name.
“You are the managing director of the Gaingels.”
Jon McLachlan, at 12:03
“It’s like Angels with a G, with a hard G in front of it.”
Lorenzo Thione, at 12:11
Wikipedia says the name mixes “gay angels” and “gaining from angels” (Wikipedia). Lorenzo told the rest of the story later in the conversation.
I started an AI company back about 20 years ago
Asked for his background, Lorenzo started with the company.
“Yeah, you mentioned some of my background, but once I sort of started my career as an operator entrepreneur, I started an AI company back about 20 years ago.”
Lorenzo Thione, at 12:18
The company was Powerset. It was based in San Francisco and was building a natural language search engine in 2006, one that tried to understand the question instead of matching keywords, using technology licensed from PARC, the former Xerox Palo Alto Research Center. On May 11, 2008, it opened a tool for searching part of English Wikipedia with conversational phrases, and on July 1, 2008, Microsoft acquired it for an estimated $100 million. Wikipedia lists Lorenzo as its product architect and a co-founder, with Barney Pell as CEO, and among its alumni, Tom Preston-Werner, who left after the acquisition to found GitHub (Wikipedia). His LinkedIn has him as founder and product architect from September 2006 to September 2008, then principal program manager for Powerset and Bing at Microsoft until October 2010 (LinkedIn). Microsoft Bing traces its roots to MSN Search, Windows Live Search and Live Search (Wikipedia).
“After a successful acquisition, one of the things I turned my attention to were the inequities and imbalances that existed in the venture capital ecosystem in terms of who this incredible engine for innovation and wealth creation was really benefiting.”
Lorenzo Thione, at 12:30
A pretty rarefied small group of people
What he saw, after the acquisition, was who venture capital was working for.
“And it was benefiting a pretty, and to some extent still is, a pretty rarefied small group of people”
Lorenzo Thione, at 12:49
He went through it group by group, starting with women.
“And it just so happened that in 2008, women already were being noticed to be receiving a fraction of the capital of their male counterparts when founding companies.”
Lorenzo Thione, at 13:09
“And there were pretty much almost no female general partners of large established venture capital firms.”
Lorenzo Thione, at 13:23
He said it was even worse for underrepresented ethnic groups, and that one gap had no one counting it at all.
“and nobody was paying attention at the additional kind of inequities that existed with respect to the LGBTQ community accessing capital.”
Lorenzo Thione, at 13:39
Wikipedia says women make up a small fraction of the venture capital workforce, and that research from Women in VC puts the share of female VC partners just shy of 5 percent (Wikipedia). Someone has since counted the LGBTQ gap. StartOut’s 2023 State of LGBTQ Entrepreneurship Report, built with Socos Labs from internal data, Crunchbase and Pitchbook, looked at 142,000 founders and 95,000 high-growth companies in the United States from 2000 to 2022. It found that LGBTQ+ founders raised 0.5% of the $2.1 trillion in startup funding, while 7.1% of the population identifies as LGBTQ+, and that despite raising 16% less funding than the average founder, they created 36% more jobs, 114% more patents and 44% more exits (StartOut).
To learn from each other, to mentor each other
His answer was an organization.
“And so what emerged was the idea of creating a space and organization that would help LGBTQ entrepreneurs to learn from each other, to mentor each other, to network with each other, to support each other, and to gain more success in starting and growing their businesses.”
Lorenzo Thione, at 14:07
“I’m co-founder and founding chair of the organization.”
Lorenzo Thione, at 14:35
That’s StartOut, the nonprofit supporting LGBTQ entrepreneurs that Wikipedia says entrepreneur Darren Spedale founded in 2009, with more than 18,000 members and chapters in eight cities (Wikipedia). Lorenzo’s LinkedIn lists him as co-founder from June 2009 and now as chairman emeritus (LinkedIn). StartOut states its mission as increasing opportunity and success for LGBTQ+ entrepreneurs, and says it supports more than 700 founders a year (StartOut).
Jon had been through it. His own company, Peacemakr, went through StartOut while he was its founder and CEO.
“and it was just an incredible experience, like nothing I’d ever expected or had been through before.”
Jon McLachlan, at 19:49
“all of the gratitude in the world for starting StartOut, the only LGBTQ incubator in the world”
Jon McLachlan, at 20:04
A nonprofit couldn’t invest directly
StartOut could teach and connect founders. It couldn’t write them checks.
“Ultimately, one of the things that the organization couldn’t do was to invest directly into the companies that it sought to help.”
Lorenzo Thione, at 14:40
“And partially, that was the nonprofit nature of the organization.”
Lorenzo Thione, at 14:50
“So we started Gaingels, and you jokingly said Gay Angels, which is certainly part of the portmanteau”
Lorenzo Thione, at 14:54
He added that the spelling with an “i” makes it read like gain, as in profit, and called it a fortunate misspelling.
“But we started out as a network of investors that were supporting directly LGBT founders.”
Lorenzo Thione, at 15:09
Wikipedia describes Gaingels as a venture capital firm headquartered in Burlington, Vermont, co-founded in 2014 by David Beatty and Paul Grossinger, that began as a small angel syndicate of LGBTQIA+ investors backing founders from the same community. In 2018 it widened its mission to diversity across venture capital, and its investments grew from $5 million in 2018 to $50 million in the first eight months of 2020 (Wikipedia). An angel investor provides capital to a business, often very early, and a growing number organize themselves into angel groups or networks to share capital and advice (Wikipedia). Lorenzo’s LinkedIn has him as a managing director at Gaingels since March 2019 (LinkedIn).
“The reality, though, was that we one day realized the opportunity and the need was much broader”
Lorenzo Thione, at 15:19
This is not about quotas
The broader version started from the cap table up. A team can be diverse in one way and not another.
“You may have a team that has two women founders and no representation from other groups.”
Lorenzo Thione, at 15:44
“And again, this is not about quotas. I despise quotas.”
Lorenzo Thione, at 15:50
“It’s really about the idea of creating paths for access to people that have the talent and the means, but not the opportunity”
Lorenzo Thione, at 15:54
So Gaingels changed into an investor that invests to make money for itself and its members, with help on inclusion as the value it adds.
“helping them with recruitment, helping them with adding leadership, adding governance, board members, advisors from underrepresented pools of talent that they would not normally have access to.”
Lorenzo Thione, at 16:50
“And ultimately, the decisions for who to bring on and who to hire were always decisions that remained with the company”
Lorenzo Thione, at 17:01
Diversifying the cap table
The last piece is the one he said nobody was talking about in 2018.
“And the last piece of that, which was not something that anyone was talking about back in 2018, is the importance of diversifying the cap table.”
Lorenzo Thione, at 17:14
A capitalization table, or cap table, analyzes a company’s ownership percentages, dilution and the value of equity in each round of investment (Wikipedia). Lorenzo’s argument is about who’s on it when the company wins.
“And if it’s always the same people who get to invest into the best companies, then it’s always the same people who get to get wealthier and more powerful”
Lorenzo Thione, at 17:37
So Gaingels lets individual investors from underrepresented backgrounds put in what can be small amounts, alongside the big funds, and that turns into a cycle.
“And it becomes this really interesting flywheel where companies want us involved because we’re value add and we’re great.”
Lorenzo Thione, at 18:23
“We do what we say we do.”
Lorenzo Thione, at 18:30
“And for our members and for investors, we create this incredible opportunity to invest in companies that they would normally not have access to.”
Lorenzo Thione, at 19:02
He said the flywheel started spinning fast in 2018, and that it made Gaingels one of the most active investment groups in venture capital, and the only one of meaningful size dedicated to inclusion across capital, leadership and governance.
Grow the pie instead of just reallocating it
Jon asked how AI, and security in particular, could help break the echo chamber in how capital gets handed out, and whether Gaingels invests much in AI.
“Yeah, we invest very heavily in the AI space”
Lorenzo Thione, at 20:38
He said the big consulting firms put AI’s impact on the global economy in the many trillions of dollars, and that this technology is different.
“we’re seeing a technology that has the opportunity to grow the pie instead of just reallocating it in some, quote unquote, more efficient way.”
Lorenzo Thione, at 21:14
“That is exciting to investors. It’s exciting to innovators and founders. It’s exciting to users and workers everywhere.”
Lorenzo Thione, at 21:24
Anytime you have a new risk, you have a new opportunity
Then he connected it back to security, where Gaingels has been investing for a long time.
“When it comes to security, we also have a long history of investing in security businesses”
Lorenzo Thione, at 22:00
“Because anytime you have a new risk, you have a new opportunity. And now that equation is just accelerating when you introduce AI in it.”
Lorenzo Thione, at 22:10
His own thesis is the containment idea from the start of the episode, put as a mandate.
“this intersection of AI-first technologies designed to combat, counteract or contain the misuse and side effects and kind of bad outcomes that a bad actor in control or using AI can inflict.”
Lorenzo Thione, at 22:28
Private markets are not symmetric
As for the echo chamber, Lorenzo said AI doesn’t change it any more than anything else does, with one exception: because everyone expects profit from investing in AI early, it’s the most competitive place to put money. And competition works differently in private markets.
“in the public market, competitiveness just determines price, right? Price goes up.”
Lorenzo Thione, at 23:31
“private markets are not symmetric like the public market are, meaning not everybody has access at any price to invest in certain companies.”
Lorenzo Thione, at 23:37
The flywheel is what gets Gaingels in the door, and its members in with it.
“we are regularly able to access, and therefore provide that access to investors who, on their own, would simply not have the ability to invest in some of these businesses.”
Lorenzo Thione, at 23:57
“Yeah, it sounds like there’s power in numbers.”
Jon McLachlan, at 24:20
“There is absolutely power in numbers.”
Lorenzo Thione, at 24:23
Venture capital is private equity for startups judged to have high growth potential, paid for with equity, and because startups face high uncertainty, those investments fail often (Wikipedia). Access to the few that don’t is the scarce thing.
What we call our Gaingels letter
Every company that joins the Gaingels portfolio is invited to sign something.
“to sign what we call our Gaingels letter.”
Lorenzo Thione, at 24:47
“It is a non-binding pledge, designed to be non-binding for a lot of reasons, because this is really about alignment of interests.”
Lorenzo Thione, at 24:49
He listed what it asks companies to consider.
“including parity in hiring and recruiting, when you’re looking at pipelines across multiple dimensions of inclusivity and diversity”
Lorenzo Thione, at 25:07
The same goes for the board and advisors, the cap table and philanthropy.
“We are signers and partners of the Give 1% organization that encourages corporations to assign 1% of either equity, profit or product to causes that they care about”
Lorenzo Thione, at 25:31
“and the adoption of non-discrimination standards that include and provide benefits for many of the categories that still are being excluded by law.”
Lorenzo Thione, at 25:46
The organization he means is Pledge 1%. Atlassian, the Entrepreneurs Foundation of Colorado and the Salesforce Foundation launched it as founding partners on December 2, 2014, asking companies to pledge 1% of their equity, product and employee time to their communities (Atlassian). Today it calls itself a global movement for corporate impact, offers a framework for setting aside a percentage of staff time, product, profit and equity, and counts 20,000 companies in more than 130 countries (Pledge 1%).
Oh, that’s not enough
Jon had seen the pledge before.
“No, it’s important to be the change that we want to see in the world.”
Jon McLachlan, at 25:55
He’d seen it before, when Peacemakr went through StartOut.
“and I remember thinking, like, oh, 1%? Oh, that’s not enough.”
Jon McLachlan, at 26:11
So he changed it to 10.
“That’s very generous. Good for you.”
Lorenzo Thione, at 26:16
“I mean, I would have loved to have given more on top of that”
Jon McLachlan, at 26:18
Lorenzo pointed at Salesforce, where 1% is a very large number. Marc Benioff, whom Lorenzo named as one of the forces behind the foundation, is Salesforce’s co-founder, chairman and CEO (Wikipedia). The point of the small number is that people will actually do it.
“it’s a small enough piece of the pie that it should be nothing but a second thought to actually do this”
Lorenzo Thione, at 26:43
“the impact on global poverty, on climate change, on so many of the causes that really can’t be solved by any one given party and really need our collective effort”
Lorenzo Thione, at 27:04
The calculator below runs the arithmetic on your own company, at Lorenzo’s 1% and Jon’s 10.
A history unlearned is a history repeated
Jon, who was recording in San Francisco, brought up a walk through the Castro.
“And when you go for a walk in the Castro, which is the gay district in San Francisco, they have placards on the sidewalks.”
Jon McLachlan, at 27:24
“And one of the placards is of Alan Turing.”
Jon McLachlan, at 27:38
“I believe a history unlearned is a history repeated.”
Jon McLachlan, at 27:44
The placards are the Rainbow Honor Walk, bronze plaques in the Castro’s business district honoring LGBTQ people who “made significant contributions in their fields” (Wikipedia). Alan Turing was in the inaugural round of twenty honorees, installed in 2014 (Wikipedia). The Castro was one of the first gay neighborhoods in the United States (Wikipedia).
“and he helped the Allies win World War II by breaking the German Enigma machine with his machine, with his mathematics.”
Jon McLachlan, at 27:50
Wikipedia calls Turing an English mathematician and logician widely regarded as the father of theoretical computer science. During the war he worked at Bletchley Park, Britain’s codebreaking center, as head of Hut 8, decrypting German naval messages, and his techniques sped up the cryptanalysis of Enigma (Wikipedia). The Enigma machine was the cipher device Nazi Germany used across all its military branches, considered secure enough for its most top-secret messages (Wikipedia). Turing earned his doctorate at Princeton in 1938 (Wikipedia), and the test came later, in a 1950 paper (Wikipedia).
A very interesting intellectual exercise
Jon explained the Turing test for listeners and asked whether today’s LLMs pass it.
“If you can make that distinction, then the machine is said to have failed the Turing test.”
Jon McLachlan, at 28:15
“And now, with all of the LLMs, it feels like these machines today with these LLMs are passing the Turing test.”
Jon McLachlan, at 28:42
The test, as Turing introduced it in “Computing Machinery and Intelligence” in 1950, was the imitation game, and the paper opens by proposing to consider whether machines can think. In the modern version, an evaluator reads a conversation between a human and a machine, and the machine passes if the evaluator can’t reliably tell which is which, whether or not its answers are correct (Wikipedia). A large language model is a machine learning model trained on a vast amount of text, and LLMs are the basis of most modern chatbots (Wikipedia). Lorenzo answered with a second thought experiment.
“Well, so the Turing test is a very interesting intellectual exercise. And there are a few of these intellectual exercises. The Chinese room is another one.”
Lorenzo Thione, at 28:58
The Chinese room is John Searle’s argument, from a 1980 paper, that a computer running a program can’t have a mind or understanding, however human it seems (Wikipedia). Lorenzo’s objection to both is that they don’t make good tests.
“But in reality, they’re very ill-defined exercises, if you actually wanted to use them as tests, right?”
Lorenzo Thione, at 30:10
“especially the Turing test, only proves or gives you information about how good that machine is at fooling a human.”
Lorenzo Thione, at 30:48
That last line is the security point in the middle of the philosophy. A cloned voice is a machine that’s good at fooling a human. It doesn’t have to be intelligent to take your money.
Tell me more about that
Lorenzo went back to an early program.
“I don’t know if you’ve ever heard of a program called ELIZA.”
Lorenzo Thione, at 31:36
“No, I have not.”
Jon McLachlan, at 31:39
“But it was this very basic program that was designed to act as a talk therapy bot.”
Lorenzo Thione, at 31:50
“like respond to half of the things that you said with things like, that’s interesting, tell me more about that, or, how do you feel about this?”
Lorenzo Thione, at 32:01
He guessed it came from the 1970s and didn’t remember who wrote it. ELIZA was developed from 1964 to 1967 at MIT by Joseph Weizenbaum. It used pattern matching and substitution to give an illusion of understanding, and its best-known script, DOCTOR, played a Rogerian psychotherapist who reflects people’s words back to them. It was one of the first chatbots, and one of the first programs capable of attempting the Turing test. Weizenbaum was surprised that people, including his secretary, attributed human feelings to it, which came to be called the ELIZA effect (Wikipedia).
Lorenzo said the same trick works without computers. Fortune tellers, in his words, are
“people who have developed a very good skill at listening, mirroring, asking the right questions, being generic enough that things pattern matched into what people expect to have a response.”
Lorenzo Thione, at 32:36
Cold reading is the name for that set of techniques: high-probability guesses, quick reading of the person’s reactions, and reinforcement of the hits (Wikipedia). Mirroring, or the chameleon effect, is imitating someone’s gestures, speech or attitude, and it builds rapport (Wikipedia). Jon heard Chris Voss in it, the former FBI hostage negotiator and co-author of Never Split the Difference (Wikipedia).
“Mirroring is a very well understood tactic in manipulation and persuasion, and there’s a number of them, right?”
Lorenzo Thione, at 33:03
The same toolkit is what makes a scam call work. A caller doesn’t need to know much about you if they can mirror you and let you fill in the rest.
Things that humans are terrible at doing
Lorenzo said the Turing test was never going to settle whether machines are intelligent, because nobody has defined intelligence or why we care about it. He’d read a LinkedIn post asking a better question.
“getting machines to do things that humans are terrible at doing?”
Lorenzo Thione, at 34:08
“Like, they can’t do it at scale, they can’t do it repeatedly, they can’t do it correctly.”
Lorenzo Thione, at 34:12
He thinks building machines in our own image, as a kind of act of creation, gets the goal wrong, and he closed the subject warmly.
“but it’s hardly the right test to think about when really looking at artificial intelligence.”
Lorenzo Thione, at 34:56
It’s absolutely compatible
Jon asked the big question next.
“Do you believe in the singularity”
Jon McLachlan, at 35:04
The technological singularity is a hypothetical point where technological growth accelerates beyond human control. In I. J. Good’s intelligence explosion model from 1965, an upgradable intelligent agent improves itself in a positive feedback loop until it’s a superintelligence (Wikipedia). Ray Kurzweil, the computer scientist and futurist Lorenzo mentioned, has written books on it (Wikipedia). Lorenzo said the idea is consistent with what we know.
“is absolutely compatible with everything we know about the world, the physics of it”
Lorenzo Thione, at 35:29
“But it’s absolutely compatible.”
Lorenzo Thione, at 35:57
What he wasn’t sure about was the outcome, and he laid out at least three.
“We have the creation of a completely new sort of type of life, right?”
Lorenzo Thione, at 36:07
“It also could simply just be a better tool that becomes more and more powerful”
Lorenzo Thione, at 36:25
“which is we are always in control of that replication”
Lorenzo Thione, at 37:30
He hopes nobody tries for the first one on purpose.
“the right thing to do is the Frankenstein kind of mode”
Lorenzo Thione, at 36:53
He means that as the thing to avoid: a being with its own needs and wants plus superhuman ability, which, by everything we know about superior life forms, would subjugate the others. And none of the three, he said, is a reason to stop.
“And I don’t think any of them kind of drives to the conclusion we should stop what we’re doing right now”
Lorenzo Thione, at 37:45
It’s not a stochastic parrot
Jon offered the skeptic’s version.
“I heard someone put it that AI is just a fancy parrot, that it reads things and it knows how to regurgitate what it’s heard.”
Jon McLachlan, at 38:18
“Well, it’s not a fancy parrot. It’s not a stochastic parrot.”
Lorenzo Thione, at 38:31
The phrase comes from a 2021 paper on AI ethics, “On the Dangers of Stochastic Parrots: Can Language Models Be Too Big?”, by Timnit Gebru, Emily M. Bender, Angelina McMillan-Major and Margaret Mitchell, which laid out risks of large language models. It frames LLMs as systems that statistically mimic text without real understanding, and Wikipedia notes the term has also been taken as an insult toward AI (Wikipedia). Lorenzo’s case against it is about how the networks work.
“there are a lot of similarities between what multilayer neural networks, which are at the core of transformers, which are at the core of large language models, and brain networks, neural networks in the brain, work in a lot of similar ways”
Lorenzo Thione, at 38:54
“it is very clear that it is able to generate sequences that have never been generated before”
Lorenzo Thione, at 39:49
“These things are not anywhere near what humans can do, but the idea that they will never approach it is kind of, I don’t know, wishful thinking for some”
Lorenzo Thione, at 40:27
A transformer is a neural network architecture built on multi-head attention, in which text is split into tokens and each token is weighed against the others in its context (Wikipedia), and an artificial neural network is a computational model inspired by the structure and functions of biological neural networks (Wikipedia). How far the similarity goes is still argued. Lorenzo’s view is that the label sells the systems short, and that betting they’ll never approach what people can do is wishful thinking.
His story is not told enough
Jon came back to Turing.
“I really believe that his story is not told enough”
Jon McLachlan, at 40:46
Lorenzo remembered a film without its name, and it came up as The Imitation Game, the 2014 film directed by Morten Tyldum and written by Graham Moore, from Andrew Hodges’ 1983 biography, with Benedict Cumberbatch as Turing (Wikipedia).
“Yeah, the way he was mistreated by his government”
Lorenzo Thione, at 40:56
“the UK government kind of issued an apology.”
Lorenzo Thione, at 41:04
In 1952, after acknowledging a relationship with another man, Turing was prosecuted for gross indecency, received probation conditional on chemical castration and lost his security clearance. After a 2009 campaign, Prime Minister Gordon Brown officially apologized for the “appalling way [Turing] was treated,” and Queen Elizabeth II granted him a pardon in 2013 (Wikipedia). The “Alan Turing law,” part of the UK’s Policing and Crime Act 2017, pardons men cautioned or convicted under the old laws against homosexual acts (Wikipedia). The apology came in 2009, fifteen years before this recording.
Asked what he’d say to Turing, Lorenzo picked a subject.
“and discuss all the ways in which the world is computation and computation is physics.”
Lorenzo Thione, at 41:31
“someone I admire very much and would love to one day have an opportunity to meet and converse with, is Stephen Wolfram.”
Lorenzo Thione, at 41:44
Stephen Wolfram is a British-American computer scientist, physicist and businessman who works in computer algebra and theoretical physics (Wikipedia). And dinner would be at home.
“I would probably make dinner.”
Lorenzo Thione, at 42:08
“Also, if I’m going to bring a celebrity to a restaurant, we’re going to get interrupted every moment by people wanting to take their selfie with them.”
Lorenzo Thione, at 42:17
We need more freedom of speech, not less speech
Jon named two well-known people from the tech world, Peter Thiel and Kara Swisher, and asked Lorenzo about them.
“Very spicy personalities.”
Jon McLachlan, at 42:43
“People are interesting. People are different. I love when people voice their opinion. We need more of that. We need more freedom of speech, not less speech.”
Lorenzo Thione, at 42:50
“And I think the marketplace of ideas is how not just innovation but social progress actually does happen.”
Lorenzo Thione, at 43:00
He said he doesn’t agree with everything either of them has said, and then he made it personal.
“Peter served on the board of directors of my very first company. I learned a ton from him.”
Lorenzo Thione, at 43:17
“And I think it’s great that there’s no one dimension to every single person.”
Lorenzo Thione, at 43:24
Thiel is a co-founder of PayPal, Palantir Technologies and Founders Fund, and was the first outside investor in Facebook (Wikipedia). Wikipedia lists him among Powerset’s investors, and Founders Fund co-led Powerset’s $12.5 million Series A in November 2007 (Wikipedia). Kara Swisher is a journalist who has covered the business of the internet since 1994 (Wikipedia).
Diversity of ideas comes from diversity of experience
Jon took it to founders.
“You have to have a little bit of this crazy. You have to be willing to break the rules.”
Jon McLachlan, at 44:04
“And I think diversity of ideas comes from diversity of experience.”
Jon McLachlan, at 44:32
“We bring our experiences with us. We have no choice but to see the world through them”
Jon McLachlan, at 44:35
He said he sees a lot of that comfort with breaking the rules in the LGBTQ community, which is a good thing for anyone building something new.
Sleep more, not less
The last question was what Lorenzo would tell his younger self.
“Yes, I would. And I would give myself the advice of sleeping more.”
Lorenzo Thione, at 45:26
“When I was young, I thought sleeping as little as I could get away with was a superpower, was something that made me more productive.”
Lorenzo Thione, at 45:33
He said he now understands how much sleep, nutrition, exercise and mental health shape productivity, creativity and the ability to have an impact.
“And I would go back and tell myself, sleep more, not less.”
Lorenzo Thione, at 46:04
After the tape
Lorenzo’s LinkedIn has him still at Gaingels as a managing director, leading investments in AI, deep tech and consumer technology while working to increase minority representation in venture capital, and it puts the firm’s record at more than $300 million invested in over 500 LGBTQ+ led companies, and over $1 billion across more than 2,400 startups (LinkedIn). The same profile lists him as co-founder and chairman emeritus of StartOut, a keynote speaker since January 2022, and managing partner since October 2008 of Sing Out, Louise! Productions, a theater and film production company whose credits include Hadestown, which won the 2019 Tony Award for Best Musical, and The Inheritance, which won the 2020 Tony Award for Best Play. Hadestown is Anaïs Mitchell’s musical, and The Inheritance is Matthew López’s play inspired by E. M. Forster’s Howards End (Wikipedia, Wikipedia).
One of those shows he also helped write. Allegiance, a musical inspired by George Takei’s experience of the Japanese American internment during World War II, has music and lyrics by Jay Kuo and a book by Marc Acito, Kuo and Lorenzo Thione. It premiered in San Diego in September 2012 and played on Broadway from October 2015 to February 2016 (Wikipedia).
StartOut today describes its work as empowering LGBTQ+ and allied entrepreneurs, and counts 28,000 people connected and 1,829 companies supported (StartOut). Its research arm, the StartOut Index, is where the funding numbers earlier on this page come from (StartOut).
And one link back to this show. Anzenna, the company Ganesh Krishnan founded and talked about in episode 34, lists Gaingels among its backers on its company page (Anzenna).
Did you catch it? A six-question quiz
Six questions from the episode. Each answer links the moment in the transcript.
Quiz · six questions
Did you catch it?
Pick an answer for each. The explanation shows once you choose.
-
What does Lorenzo call the area of AI he focuses on as an investor?
- Detection
- Disruption
- Containment
c. "And one of the areas that I focus on is what I have defined or called containment." Transcript, 2:02.
-
What did Lorenzo say to set up with the people you'd send money to?
- A video call before any transfer
- Passwords and shared secrets
- A second phone number
b. "make sure you have passwords and shared secrets that you don't discuss with anyone else" Transcript, 11:50.
-
What couldn't StartOut do, that Gaingels could?
- Invest directly in the companies it helped
- Run events in more than one city
- Mentor founders outside San Francisco
a. "Ultimately, one of the things that the organization couldn't do was to invest directly into the companies that it sought to help." Transcript, 14:40.
-
What did Lorenzo say about quotas?
- They're the fastest fix
- They work for boards but not for hiring
- He despises them
c. "And again, this is not about quotas. I despise quotas." Transcript, 15:50.
-
What did Jon do with the 1% pledge at Peacemakr?
- Kept it at 1%
- Changed it to 10%
- Gave it to the investors
b. "and I remember thinking, like, oh, 1%? Oh, that's not enough." Transcript, 26:11.
-
What does the Turing test really measure, by Lorenzo's account?
- How good a machine is at fooling a human
- Whether a machine is conscious
- How fast a machine can reason
a. "especially the Turing test, only proves or gives you information about how good that machine is at fooling a human." Transcript, 30:48.
Would a cloned voice get through?
Lorenzo’s advice was for families, and it works for companies too. Eight questions on whether a familiar voice and a good story could get money out of yours.
Scorecard · eight questions
Would a cloned voice get through?
Answer for how your company works today. If two answers fit, pick the lower one.
-
When a caller asks to move money or change bank details, how is it checked?
- The voice or the caller ID is enough
- Sometimes we call back
- Always a callback to a number we already had
"just stop relying on what you see and what you hear, or rather the characteristics of what you see and what you hear" See Make sure you have passwords and shared secrets.
-
Do the people who can move money share a phrase that never appears in writing?
- No
- Some of them
- Yes, agreed in person and changed when someone leaves
"make sure you have passwords and shared secrets that you don't discuss with anyone else" See Make sure you have passwords and shared secrets.
-
Can one person send a wire or change payment details alone?
- Yes
- Only above a limit does it take two
- Always two people, on two channels
"So your defenses completely go down, and you become much less rational and much less sort of wise to those risks." See A politician was actually testifying to Congress.
-
Has your team heard what a cloned-voice call sounds like?
- Never covered
- Mentioned in training
- Practiced with a realistic exercise
"The reality is that we are dealing as a society with these advanced types of scams and social engineering and otherwise already." See Are you sure that it's actually your best friend?
-
What happens when a caller pushes urgency or secrecy?
- People hurry to help
- It depends on who answers
- Urgency is the cue to slow down and verify
"because all of your defenses go down when your primordial brain, the one that acts on instincts and really fast to react, is getting all of these signals that say, this is your son." See A politician was actually testifying to Congress.
-
Do you assume your executives' voices can be cloned?
- We've never thought about it
- We know, but haven't acted
- Yes, and we plan around it
"You can't trust the voice on the phone anymore." See You can't trust the voice on the phone anymore.
-
Is there a fast, blame-free way to report a strange call?
- No
- Email the security team
- One channel, and people use it
"But we still have to deal with the edge cases, I would say, of that, that there are evil people in the world, and hence security, right?" See 99.9999% of people in this world are good.
-
Do the people at home have their own code word?
- No
- Some of us
- Yes, and we talk about it at work
"I wish that were a scenario that was sci-fi and made up and far from being possible." See Are you sure that it's actually your best friend?
A familiar voice and a good story would probably get money out today. This week, put a callback rule on every request to move money or change bank details, and agree a shared phrase with the people who can approve it.
Some checks exist, but they depend on who answers the phone. Make the callback and the second approver mandatory, and run one realistic exercise so people hear what a cloned call sounds like.
A cloned voice would run into a process, not a person. Change the phrases when people leave, test the process once a year, and share the habit with your team's families.
What is a 1% pledge worth?
Lorenzo described the 1% pledge, and Jon raised his to 10%. The calculator runs both on a company you pick. The company value, the team and the 2,080-hour work year (40 hours a week for 52 weeks) are our examples. Put in your own.
Calculator
What is a 1% pledge worth?
Four numbers: what the company is worth at exit, the share of equity pledged, the people on the team, and the share of their work time pledged.
Pledge 1% of a company that exits at $100 million and the pledge is worth $1.0 million, against $10.0 million at Jon's 10%. 1% of the work time of 50 people is 1,040 hours a year, about 130 working days.
The 1% is the pledge Lorenzo described on the tape, and the 10% is what Jon said he changed his to. The $100 million exit, the 50 people and the 2,080-hour work year are our examples, not benchmarks. Pledge 1% itself counts equity, product, profit and staff time.
From Turing to Gaingels and after
Everything on this page sits on one timeline, from Turing’s doctorate in 1938 to Gaingels and StartOut today. Filter it by thread.
Timeline · 1938 to 2026
From Turing to Gaingels and after
Filter by thread. Dates are from the public record except where marked as part of this show.
- Turing's doctorate
Alan Turing earns his doctorate at Princeton (Wikipedia, on this show).
- The imitation game
Turing's paper "Computing Machinery and Intelligence" introduces the test (Wikipedia, on this show).
- Turing is prosecuted
He is prosecuted for gross indecency after acknowledging a relationship with another man, and loses his security clearance (Wikipedia, on this show).
- ELIZA
Joseph Weizenbaum begins the chatbot at MIT, and finishes it in 1967 (Wikipedia, on this show).
- The intelligence explosion
I. J. Good describes a self-improving intelligent agent (Wikipedia, on this show).
- The Chinese room
John Searle publishes "Minds, Brains, and Programs" (Wikipedia, on this show).
- Founders Fund
Peter Thiel, Ken Howery and Luke Nosek found the venture fund in San Francisco (Wikipedia, on this show).
- Powerset
Lorenzo starts the natural language search company as founder and product architect (LinkedIn, on this show).
- Powerset's Series A
$12.5 million, co-led by Foundation Capital and The Founders Fund (Wikipedia, on this show).
- Searching in plain English
Powerset opens a tool for searching part of English Wikipedia with conversational phrases (Wikipedia, on this show).
- Microsoft buys Powerset
For an estimated $100 million (Wikipedia, on this show).
- Sing Out, Louise! Productions
Lorenzo becomes managing partner of the theater and film production company (LinkedIn, on this show).
- StartOut
The nonprofit for LGBTQ entrepreneurs is founded, with Lorenzo as a co-founder from June 2009 by his LinkedIn (Wikipedia, on this show).
- An apology
Prime Minister Gordon Brown apologizes for the way Turing was treated (Wikipedia, on this show).
- Allegiance premieres
The musical, with a book by Marc Acito, Jay Kuo and Lorenzo, opens in San Diego (Wikipedia, on this show).
- A royal pardon
Queen Elizabeth II pardons Turing (Wikipedia, on this show).
- Gaingels
David Beatty and Paul Grossinger co-found it as an angel syndicate of LGBTQIA+ investors (Wikipedia, on this show).
- The Rainbow Honor Walk
Alan Turing is among the first twenty honorees on the Castro's sidewalks (Wikipedia, on this show).
- The Imitation Game
Morten Tyldum's film, with Benedict Cumberbatch as Turing (Wikipedia, on this show).
- Pledge 1%
Atlassian, the Entrepreneurs Foundation of Colorado and the Salesforce Foundation launch it (Atlassian, on this show).
- Allegiance on Broadway
It runs through February 2016 (Wikipedia, on this show).
- The Alan Turing law
The UK pardons men convicted under the old laws against homosexual acts (Wikipedia, on this show).
- Gaingels widens its mission
From LGBTQIA+ founders to diversity across venture capital (Wikipedia, on this show).
- Peacemakr
Jon co-founds the company, which later goes through StartOut (LinkedIn, on this show).
- Managing director at Gaingels
Lorenzo's role at the firm, by his LinkedIn (LinkedIn, on this show).
- $50 million in eight months
Gaingels' investments, up from $5 million in 2018 (Wikipedia, on this show).
- Stochastic parrots
Gebru, Bender, McMillan-Major and Mitchell's paper on the risks of large language models (Wikipedia, on this show).
- The StartOut Index
LGBTQ+ founders raised 0.5% of $2.1 trillion in startup funding from 2000 to 2022 (StartOut, on this show).
- Congress hears about AI scams
A Senate Aging Committee hearing on how scammers use AI, with a father's account of a cloned call (govinfo, on this show).
- The recording
Jon and Lorenzo talk, after Peacemakr, by Jon's account (on this show).
- Episode 53 airs
The episode goes out on Podbean and Spotify (Podbean, on this show).
- Gaingels today
More than $300 million in over 500 LGBTQ+ led companies, by Lorenzo's LinkedIn (LinkedIn, on this show).
- StartOut today
28,000 people connected and 1,829 companies supported, by StartOut's count (StartOut, on this show).
What to do this week
Five things, in the order the episode suggests.
- Agree on a shared secret at home. Pick a phrase with the people you’d send money to, in person, and agree that any call asking for money gets the phrase or a callback.
- Put a callback rule on money at work. Any request to move money or change bank details gets verified on a number you already had, and above a limit, by a second person on a second channel.
- Score your company. Take the scorecard with whoever approves payments, and fix the lowest answer first.
- Run the pledge numbers. Try the calculator on your own company, and read what Pledge 1% asks for.
- Get help with the parts you can’t staff. Our vCISO Services can write the payment and verification policies and run the exercise, our Counter Business Espionage & IP Protection team handles the social engineering and insider side, our AI Product Red Teaming tests whether your own AI product can be turned against your users, and you can book 15 minutes with us.