The investor Naval Ravikant recently posted this on the already-faded-Twitter-competitor app Airchat:
There's an old Sun Tzu line that goes something like, if you sit by the river long enough, you will see the bodies of your enemies float by. And I try not to have enemies.Why give them space in my head? But I will say that when I've seen people doing shady things in my life, if I've waited 10, 15, 20 years, yeah, the bodies float by.
It has been discussed ad nauseam how the low interest rates of the past two decades enabled a lot of excess and bad behavior in the startup world. Understandably, startups make headlines because they’re public facing. People want to read about flashy companies like WeWork burning billions of dollars — acquiring wave pool startups and smoking weed on private jets — before going bankrupt, because they make products that people use daily. Low interest rates fueled precipitous valuations and a lot of absurd behavior because it seemed like founders could get away with it so long as there were ample exit opportunities.
On the investor side, there has been admittedly less headline-grabbing drama. It happens sometimes — think Mike Rothenberg, or the travails of Chamath Palihapitiya and his firm Social Capital. But VC is a small, insular world. A lot of behavior stays quiet, either because there’s a power imbalance between investors and startups, or because people don’t want to air out business disputes publicly. Sometimes it takes quite a while for the information to trickle out of backchannels and into the light.Sometimes it never does.
It’s under that context that I began looking into whispers about a firm called Vol. 1 Ventures and its partners Ian Kar and Stevie Cline.
The firm, which markets itself as a seed-stage investment and startup advisory shop, drew attention recently after partner Ian Kar was called out publicly on Twitter for annual unpaid K-1 and Delaware franchise fees related to a syndicate or SPV (special-purpose-vehicle). In a since-deleted tweet (captured here), Nik Milanovic, a general partner at The Fintech Fund, alleged that Kar did not respond to contact through multiple channels requesting he send money owed for annual legal bills. “We have outstanding accounting + legal bills for our 2020 SPVs, the tweet read. “I’ve reached out to you over the past 4 weeks by text, WhatsApp, Telegram, Twitter DM, Venmo, and multiple emails but haven’t heard back.
Milanovic’s fund is an investor in fintech companies including Ampla and Syro, among others. After the tweet was published, Kar replied and resolved the issue. Milanovic did not comment for this story.
SPVs allow individuals to pool their money into one bucket and invest in startups as a single entity, essentially enabling high-net worth individuals to invest in private companies without needing to cut a huge check. For startups, SPVs are useful because they keep the cap table clean rather than filling it up with lots of individual investors.
In isolation, the dispute with Milanovic wasn’t major. But speaking with numerous individuals who have worked with Kar and his partner — in Vol. 1 and life — Stevie Cline, I found a history of strange and inexplicable behavior.
Through a legal representative, the two declined to respond to questions for this story.
Kar and Cline have, over the years, built respectable audiences in the niche of VC and tech Twitter, with tens of thousands of followers between them. Among other things, Kar previously served as a fintech reporter at Quartz, worked on product at Acorns, and started an independent financial technology newsletter, Fintech Today, which was eventually acquired by the media company Workweek. Cline is a trained lawyer with degrees from the Ohio State University and Georgetown Law.
In looking into their track-record, I was able to confirm the duo have cut small personal checks into some companies, like Loyal for Dogs and Leda Health. But multiple sources have alleged the pair committed to invest in other startups, like DTC company Couplet Coffee, only to go dark and never wire funds. Kar and Cline through counsel would not offer comment regarding these allegations, so it’s unclear why such investments may have fallen apart.
Neither Couplet nor other startups that allegedly failed to receive funds would respond to questions for this story. However, a testimonial from Couplet founder Gefen Skolnik was removed from the Vol. 1 Ventures website sometime between May 2023 and March 2024, according to archives from Wayback Machine. Other founders with testimonials on the site did not respond to requests for comment.
The website for Vol. 1 appears to have been taken offline sometime in early 2024.
Committing to invest in a startup only to go quiet is considered a cardinal sin in the world of venture capital. One investor who spoke to me said they have witnessed startups run out of funds and die after committed capital never arrived. “It felt awful,” one founder told me about not receiving funds from Vol. 1. “I trusted them and thought we were friends too.”
More than ten people who have worked with Kar and Cline in the past spoke to me for this story. Most people wanted to speak on background, a kind of anonymity which protects them from being identified by name. That required me to be diligent about finding multiple people with similar experiences or recollections of the same events to feel confident about their veracity. Anecdotes are based on the recollections of multiple sources, and in some cases backed up by emails, text message conversations, or other records.
After I began reporting this story, Kar and Cline through their legal counsel sent cease-and-desist notices to former business partners — including individuals I hadn’t spoken to for this story. The notices demand that they end any communication with me regarding this story and retract any potentially defamatory or misleading statements made regarding them or Vol. 1 Ventures. According to one source, they also contacted the limited partners of other firms to suggest their investors were spreading lies about Kar and Cline.
On April 16, Kar and Cline through counsel filed a restraining order against me in San Francisco Superior Court. Their attorney has, among other things, tried to raise doubt about my credibility as a reporter because I am publishing this story independently, despite the fact that journalism, unlike being a lawyer or a doctor, does not require any licensure. They also alleged that one of my sources was attempting to extort them by speaking to me, demanding some form of compensation in order to cease communications with me.
Also as I began looking into allegations about Vol. 1, Cline posted a tweet thread on April 5 announcing that she has been diagnosed with cancer. She has since taken a step back from social media, deleting her account.
Filings with the Securities and Exchange Commission (SEC) indicate that Vol. 1 Ventures registered a fund in 2022, but there are no subsequent filings indicating that the firm ever raised any money.
Cline in particular has promoted herself on Twitter as one of the better actors in the VC industry, frequently referencing her background as a lawyer to support her credibility — records from the New York State Bar confirm she attended Georgetown Law. And she has regularly stated in the past that she consulting work, advising startups in regulated industries on how to play it by the book. Vol. 1 pitch to founders is that the firm will not just invest in their companies, but also advise on legal issues and help “keep you out of jail,” according to archived versions of the website. But that messaging appears in stark contrast to what people say about the behavior at times of Kar and Cline.
“Stevie tried to court me into being an LP for the fund, and Ian kept bringing up that they would like me to be an EIR,” said one source, who like most, requested to remain anonymous. “After spending some time [with Kar and Cline] something was just off and some things they said were just blatant lies that were easily disproved. I distanced myself from them and their ‘fund’ when things didn’t add up with what they were saying and doing.”
One such comment allegedly made by Cline that was easily disproven, and which multiple sources cited to me, was a claim that she was cousins with an individual named Marissa Curry. It wasn’t true, and Cline was later called about it publicly, deleting refences to Curry from her Twitter account.
Curry was purportedly hired help do engineering work for a Web3 project called $APING, which Cline had taken on as CEO in January. Cline described the project in a Medium post as seeking to empower adult creators to earn money and sidestep the traditional banking system, using an $APING coin to facilitate transactions. Curry, currently a senior in college, was allegedly owed money related to the project, providing Kar and Cline wire details for a Chime bank account. Chime does not accept person-to-person wires as it’s not technically a bank, but a direct deposit from a business account should have been delivered.
“Ian tried to pay her via wire but Chime doesn’t accept wires apparently,” said a source familiar with the situation. “But that’s suspicious because what type of company pays an employee from a personal account?” They added, “I tried to warn Marissa as there were already whispers that Ian and Stevie had not paid contractors.”
When Curry offered alternative ways for Kar and Cline to send the money, including Cash App, it never arrived. Curry did not comment directly for this story.
Another individual who previously completed work for Kar and alleged they never got paid said they are happy that the situation was finally coming to light. In text message conversations I reviewed, the individual cites Cline’s background as a lawyer and writes, “If she is who she says she is, why can’t they ever pay their bills?”
In a Telegram for the $APING project, Kar commented on the situation with Milanovic and the SPV, writing “I started a syndicate w someone 4 years ago and I left 3 years ago, yet still expected to pay fees for some reason. Don’t think it’s a big deal.” SPVs filed in Delaware come with annual requirements including franchise fees and issuing K-1s to underlying investors.
The Telegram chat blew up with concerns about the status of the progress after Cline let community members know she would be stepping back due to her cancer diagnosis. The value of the project’s associated token plummeted as members raised concern about progress with development of the project and questions surrounding who is now developing the service.
“The amazing team touted by Stevie and Ian is nowhere to be found” lamented one member. “Token down by 99%.”
“So the GP of a fund becomes CEO of a company,” another wrote, “2 months later investors lose 100% and the CEO leaves.”
Cryptocurrency is inherently volatile, and it’s possible the crash was caused by holders of the $APING coin looking for a financial return who were simply spooked by Cline’s departure. There’s no proof that Cline or Kar sold off any tokens — or “rugged, ” in crypto parlance — the project as the value of the coin tanked. Cline alleges in messages in the Telegram chat that she was harassed by participants in the community, even saying individuals had shown up at her home and threatened to kill her dog if they didn’t get their investments back.
Kar later followed up in the Telegram chat saying that an initial version of $APING was in the process of going live, and that a rebranding would be shared within the week. But in subsequent weeks since the fallout, the Telegram chat went quiet without updates.
“I’ve had people tell me they’ve gotten calls from creditors and stuff as it relates to Ian/Stevie,” added a source, who should be noted had a financial interest in $APING. “I honestly think they just feel the walls closing in. [Cline] was tweeting 2 weeks ago about how much crypto consulting work she was doing and then deleted it when this all came out.”
Fintech Today, the newsletter ran by Kar before starting Vol. 1, covered all things related to the financial technology area of the startup industry. It was acquired for an undisclosed sum by the media company Workweek in 2022. Colleagues who worked with Kar on the newsletter generally did not want to comment on the experience besides saying he did not produce much content during his time at Workweek. Kar spent only a brief time at the company before being pushed out for unclear reasons. He also spent only 6 months at Acorns.
“It’s actually a shame because Fintech Today was a great community before [Ian] burned it all down.’']
It’s unclear why Kar or Cline have behaved in the ways they apparently have, stiffing business partners on bills and committing capital to startups without following through. Or why they presumably thought this conduct would never come back to bite them. Sources who have worked with Kar have described him as smart and having good intentions, but also believe he is unable to follow through on his ideas, and tries his best to avoid the consequences of bad business decisions.
Investigating this whole story, I was conflicted about whether or not to write anything on it at all. I understand the potential ramifications for the subject of a story like this can be significant. Ultimately, however, the number of people who spoke to me expressing frustration towards him was overwhelming enough that I decided it was worth documenting.
Kar and Cline’s legal counsel has asserted that my sources are unreliable, and that one of them is extorting Cline and Kar for money by essentially speaking to me until the two pay them some money. My understanding is that they are referencing Curry, whom a source says has requested money she’s owed before she would agree to a cease-and-desist.
Asked about their motivations in speaking to me about Vol. 1, one well-known VC said they did so out of a strong belief that bad actors need to be called out. “They are bad for the ecosystem.”
In an article from 2022 published by Workweek following the collapse of cryptocurrency trading platform FTX, Kar wrote about an experience he and Cline had with the now infamous firm. He writes:
Stevie went outside for a phone call while I worked on some stuff inside. She came back with a curious look on her face.
“Everything OK?” I asked.
“Yeah I just spoke to FTX again.” The FTX folks was impressed because, from what we’ve heard, they had originally tried to go to the Bermuda over the Bahamas, and were rejected. How was Stevie doing it? They were also super curious around Stevie’s lobbying experience—they asked for details on which folks Stevie knew in DC, and apparently there was very little overlap and FTX was eager to speak to the regulators and politicians Stevie knew and had worked with (Stevie is a healthcare and crypto lobbyist for Vol. 1 Ventures.)
“Uh we got a weird offer,” Stevie said. “FTX said they’d be open to putting in a small check into the fund, around $2.5 million, because that’s all they can do into funds from FTX. But they also said that Sam would back the whole fund and give us $30 million if we have them as an exclusive incubation partner.”
Kar says that Vol. 1 Ventures held cursory talks with FTX about becoming an LP and discussions never went anywhere.
It’s not unheard of that FTX might put $2.5 million into an early-stage fund like Vol.1. Before its collapse, the firm threw around its customer’s funds investing in a lot of initiatives — including investments into startups like Anthropic, which ended up being lucrative. Cline and Kar did not off comment on this, or provide evidence of any correspondence with FTX, such as screenshots of emails. It’s unclear what type of lobbying work Cline has conducted that got FTX’s interest.
As a power user of Twitter/X for 14 years, something I have been thinking about a lot lately is how there’s so much noise to sift through in order to find the signal. Inspiring stories that aren’t true, or tweets making outrages claims in the interest of “engagement farming,” generating a lot of attention in order to earn money through X revenue-sharing.
It’s easy to just accept what you see on Twitter as true, because the alternative — scrutinizing everything you scroll past — would drain a lot of mental bandwidth. It’s easier to just accept what conforms with your worldview and scroll on. And building a strong Twitter presence can pay off. I know of at least a few founders who have raised rounds for their startups primarily off their large networks on the platform. Hollywood is similar in that who you know alone can unlock a lot of doors.
But having significant engagement on Twitter should not itself be an indicator of someone’s credibility or lack thereof.
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