Alex Shipillo

Thrilled to share the HUGE news that Clio has raised the largest funding round in Canadian tech history - $900M USD on a $3 Billion USD Valuation!! Congratulations to the entire Clio team who have worked extremely hard to accelerate growth and drive this incredible outcome! 🚀

When we moved to a new neighbourhood in 2021, the only daycare in our area that was willing to take our toddler was Chabad. We got so much more than a daycare. We were welcomed into an incredibly supportive community; without judgement. Our 3rd starts at Chabad this fall. 💙

@itscoachgoodman Very cool. We have 3 kids of similar age, also in Toronto, so very curious to follow. Where have you taken the family in previous years for longer trips?

Flying out. Leaving Toronto for six months. First stop is Abu Dhabi followed by three months each in Sanur, Indonesia (Bali) and Kamakura, Japan. My kids are 8, 3, and 7 months. This will be the 13th consecutive winter abroad for 4-6 months. Our trip this year is bigger than previous years. I’m nervous. There will be hard times. The hard times are the point. Challenge and exploration builds us up and brings us together. I’m excited to escape the frenetic pace of Toronto. The go go go. The hustle mentality. I like that energy. Then I don’t. And I need to breathe a bit more, aimlessly walk, and get away from social and professional responsibilities. This season we’re entering will be slower. More family. More fitness. More books. Less connectivity. Once done, I’ll be excited once again for the next season of hustle when we return back to Toronto. That’s how we’re designed. Us humans. To have seasons. Refreshers. When something ends, we experienced renewed energy. There’s no limit to how many times we can repeat this cycle. Here’s the two most common questions that I get about our lifestyle: Isn’t the travel hard? Yeah, travel days suck. But we won’t die. And also, modern flight is a miracle. And so, whenever I feel beaten down on a plane, I just look out of the window. What do you do for school? Calvin’s in public school in Toronto. We unenroll him when we leave and find a local school abroad. This year we are doing two cohorts with Boundless. They have school for the kids. Both Calvin and Jaden are enrolled. I like the mix of the structure of public school and self-directed learning when we are abroad. Homeschooling did not work for us, or our children. Welp, off on another adventure. Excited to share the journey with you. And grateful for a healthy, strong, and incredibly competent (and super hot) wife leading the charge. -Jon

Huge day for @goclio! Grateful to be part of this amazing team. 💙 I’m almost eight years into the journey, and we are still just getting started! 🚀 x.com/i/trending/198…

@ZarnaGarg Can’t wait! I really think you’re going to be able to relate to this group. 🙈 😂

Its gonna be 🔥 (finance bros weeping from the sidelines)

She's coming to ClioCon.com in 3 weeks to perform in front of 3,000 legal professionals! Thank you @realEstateTrent for helping me "discover" Zarna - we're going to have a lot of fun and lots of laughs.

But as soon as I heard about Zarna, I knew that we needed to get her at our event! Zarna is having a massive year, including comedy specials, touring with Amy Poehler and Tina Fey youtube.com/watch?v=Y0D6WO… and now...

What does @realEstateTrent have to do with a Legal Tech conference? StripMallGuy is one of my favorite accounts. I know nothing about Commercial Real Estate, but I love his content. Earlier this year, Trent shared a story about his friend @ZarnaGarg. x.com/realEstateTren…

@ZainManji Congrats from a 3x! We found the biggest jump to 2 was getting very comfortable with divide and conquer parenting for the first 9-12 months.

Officially a girl dad of two 🥰 💕 If anyone has tips, please share, we’re all ears!

@Alex_Danco @a16z Congrats, Alex!

I’m joining @a16z ! After five years at Shopify, I’m moving onto my next adventure in life, and heading to Andreessen Horowitz. Shopify is an incredible place, and Tobi is one of the great founders of our era. I’ll remember those years as one of the golden chapters of my life. Now, onwards! I’m joining a16z as Editor at Large, and I’ll be responsible for the written output of the firm. A16z has always prioritized great thinking and writing as a deliberate instrument of the firm’s purpose and power. It starts with Ben and Marc: both generationally talented high-agency thinkers, writers, and company builders. And there’s a burning new energy in the firm today, brought by @eriktorenberg - who I’ll work with closely as he takes a16z’s narrative presence to a new level of ambition. Writing is power transfer technology I’ve had a few different vocations over the years - I’ve been a founder, touring musician, venture associate, worked at Shopify - but most people on the internet know me from my writing online. I’ve been blogging since my early twenties, and in that time I’ve seen different online content metas come and go - the golden years of VC blogs like AVC and Haystack, the Medium years, now Substack; the rise of “Go direct” and the crisis of traditional media. What hasn’t changed is how valuable great writing can be. Something special happens when you give someone words to express an idea they always knew, but couldn’t articulate: you give them power. And it didn’t cost you anything. “Power transfer technology” is what the business of VC is. Why does a VC firm care about content? It can’t just be to advertise the firm; or promote their partners and their theses. Those are both consequences of success, but they can’t be the actual goal. The primary objective of a VC firm’s content, particularly their written output, should be to give founders power. The goal is to give them writing that transforms them into someone with more legitimacy, which is what power really is about. Traditional media sometimes helps you accomplish this. A well-written op ed, thoughtfully crafted, can serve this purpose. But I think bloggers are naturally better at this craft, because bloggers have to grow their franchises under the constraint of not having built-in distribution. If you’ve mastered the craft of writing online, you know something important about how to reach and influence people, and what exactly it is you offer to an audience that gives them power. Blogging is a trade Winning, for bloggers, means writing the reference take on a good topic. My favourite example of this is how Byrne Hobart broke out with his piece on the 30-year mortgage. It’s kind of surprising that this kind of post had such influence - it’s wonky, it’s not written for a general audience whatsoever. But it turns out that people think and talk about their mortgages a lot, and like to feel competent when they do. Reading that piece equips them with a kind of legitimacy to speak on the topic. One lesson hiding in plain sight here is that most of the audience of any successful post does not actually read it. They are told it by someone who did read it. There’s a primary audience who carefully reads the piece and does the cognitive work of “restructuring their consciousness” (Walter Ong coded) around good writing. And then there’s a secondary audience, who are re-told the content, either verbally (including group chats, podcasts, Youtube) or in other oral formats like Twitter. (This is broadly true both inside and outside of organizations; e.g. a lot of work goes into writing an annual plan, which only a small number of people actually read, but a lot of people are “re-told” in some way.) The primary audience gets something out of this sequence of events: they get power. This is the great secret of writing in public: the writer and primary audience both put in effort (to pack and unpack the idea); and they jointly reap the rewards, which is the legitimacy earned when the idea gets subsequently retold verbally to the wider secondary audience. This is why, paradoxically, to reach the widest audience, you write to the narrow audience. Your objective as a writer is to give your primary audience material they’ll want to re-tell. They do the work of translating it to wider audiences in specific contexts; you do the general articulation in rich detail. The secret of magic is to transform the magician Today, there’s an amazing idea-sharing format that’s swallowed a lot of the “smart people discourse” on the internet, which is podcasting. The rise of podcasts has been astounding to watch, in the six years since I wrote The Audio Revolution. And a16z has both a great past and a great future in this media format, especially with Erik at the helm and seeing the caliber of talent he’s bringing on board his New Media team. But podcasts are not enough on their own. Great writing, which has gone through the crucible of thinking and editing, transfers something into the reader, and transforms something within the reader, that talking does not. I know a lot of smart people who correctly intuit that blogging is powerful, but can’t justify it on a return-on-effort basis compared to other ways of getting their message out. This is a mistake. Writing matters. It takes more effort to read something than to listen to it. (And much more to write something than to talk about it.) The cognitive work of writing and reading is a real cost, but the benefit is that you get “restructured consciousness” from factoring and negotiating with the idea in written form. When you read an important idea and put in the work to understand it, you gain the subconscious competence and legitimacy to talk about it: you are transformed into someone with more power. Whereas, when you hear an idea, you can usually repeat the idea but not with the same authority. The deep competency is not transferred to the same degree. This is an important idea to understand in a world where most of our information diet is shifting towards oral communication in various forms - “the internet village.” Now, people have been complaining that “nobody reads anymore” for decades - the point here is, the benefits of reading have never been more disproportionate, nor less obvious. The farther we move towards being a default-verbal information culture, the more powerful the trade between writer and primary reader, but the less obvious it is to do. (Why write things if people would rather watch or listen?) If your goal is “I want to maximize the number of people who receive my message” then oral formats like podcasts, Youtube, and Twitter will appear like the obvious choice. But if you articulate the goal as “I want to give people power” then clearly you’ve got to write something down. Founders are customers for legitimacy I remember some days when I was a founder and no one would take me seriously, except for when I could produce a blog post from someone like Paul Graham or Semil Shah and speak to that idea. Something incredible would happen in those moments - people would actually listen to me, as if I’d suddenly become magic. Magic works because it is communication. The founder equipped with the VC’s writing should communicate something higher-signal than the founder alone. Ask, “what must be true of the content for this statement to become real?” and you’ve got a good guide for what kinds of things to write. This relationship between VC and founder scales all the way up to real power-politics: the job of the VC firm is to be the “legitimacy bank” where founders (and other high-agency people) can go to take out legitimacy on credit, or make a legitimacy deposit. I find this to be a wonderful way to frame the founder-VC relationship because it does NOT imply the VCs are the “grownups” in some patronizing sense: it celebrates legitimacy as a thing that VCs and founders incept together, just like how blogging is thing that the writers and their primary readers incept together. This is why VC blogs were such a good product in their heyday. As the “free tier” of the VC, it naturally frames the relationship as one where legitimacy is jointly incepted (by the writer and primary reader), not as one that’s benevolently bestowed. The meta is different now, but the purpose is the same, and I think a16z is probably the best spot in the world to pursue that craft and that thesis. I’m incredibly fortunate to get to join this group of talented investors and company builders, towards a mission that’s never been more important: giving the world’s founders the power they need to build a bright future. Let’s go!

I am thrilled to announce @goclio is acquiring @vlex, marking a new era in AI-powered legal technology. We’re bringing together legal research, practice management, and advanced AI to create the first end-to-end platform that unites the business and practice of law 🚀 clio.com/about/press/cl…

@kamilrextin @get42agency Give them a short case study where you don’t provide a lot of data, but tell them very explicitly that they can ask for any data they need to help in their presentation. High correlation between those that ask for data and have good outcomes.

@alexshipillo @get42agency Hard on both sides I am sure. Any tips on hiring marketers 🤣

Been interviewing for 3 weeks for DG role(s) @get42agency Biggest learning: Big logos on LinkedIn & titles don't translate into ownership, high agency or accountability. A ton of marketing folks look great on paper but very light on experience & outcomes they owned. The bigger the logo, the higher the change they are just playing coordinator across teams and don't have complete ownership of a specific outcome.

Time to update the old profile. ❤️ ❤️ ❤️

Thrilled to see Canadian vertical SaaS continue to thrive! Congrats to my friends at @JaneRunsClinics on the funding and thanks for having a great product that I use weekly! 🇨🇦 🚀

@AmandaMGoetz We did Japan for ours and it was incredible. Hakone was wonderful onsen relaxation. Rest was exploration. Japan is a very relaxing country to travel to because it’s so safe, no scams, extremely organized. You’ll love it.

We are deciding honeymoon locations. We have it narrowed down to: Bali Bora bora Japan Time of year: spring 2026 We want a mix of relation and exploration. It’s not often we can take a 2 week trip without my kiddos so want to make the most of it!!!

@darynakulya @JurajPal @goclio @OpenPhone Huge opportunity!! Very excited.

@JurajPal @goclio @OpenPhone So exciting! cc @alexshipillo - looking forward to partnering up

We’re starting work on an integration with @goclio here at @OpenPhone. If you’re in the legal space, I’d love to hear your thoughts — what’s one feature that would make this integration a game changer for you? cc @darynakulya

@BPindulic Feel free to reach out by email. Firstname.Lastname @ Clio

We built this on spec using our own dollars to fund a test campaign which worked incredibly well, for context. It exceeded our expectations and we'd now like to work with a company with some traction/scale to dial this up

Who is building in the Legal AI space? We have a client that we've built a lead machine for and engineered their entire Mar/Sales Ops stack, yet they are unsatisfied for reasons we do not understand. Would like to chat with others in the space as this is too good of an industry to not keep dealing in...

@markmacleod_ Congrats on the start of the next era!

End of an era. If you know, you know.... My OG domain from when I started blogging in 2007....

@kamilrextin Yes, good lead source in our category. Although, I don’t think that having 5 vendors call you ASAP is a great buyer experience. :)

Has anyone in the history of B2B ever closed a customer from Software Advice?