About
Articles by Ben
Activity
3K followers
-
Ben Leszcz shared thisLast year, on my birthday, I flew to West Palm Beach and rented a car on an expired driver’s license. Thanks to my semi-witty repartee, I distracted the agent from the fact that, as of that day, it wasn’t quite legal for me to drive. After a courtesy upgrade, I drove my Mustang south to Boca Raton to meet a new client: a private equity firm led by Sunju Patel and Glenn Alba. Then, I sat down with each person at the company in order to understand what made it special and different. What followed was a series of thoughtful discussions with sharp, lovely people. I learned that Sunju and Glenn are very different leaders who balance one another beautifully. I saw an organization whose people are a genuine competitive advantage, with the capacity to spot opportunities that others overlook or underestimate. At the time, the company was called TMGOC Ventures. This week, it relaunched as Montford Group, with a new brand and website by StudioDA. We’re incredibly proud of the work and look forward to sharing more Montford projects in due course. After that day of interviews, I joined the team for dinner. We toasted a new relationship—and my birthday. (Thank you, Jessica D. Reid.) And, in case you’re wondering: I avoided the Florida Highway Patrol (and promptly renewed my license upon returning to Toronto). Congratulations to the Montford Group team. Thank you for trusting us with this project. https://montfordgroup.com
-
Ben Leszcz shared thisThe Bentway turned a grungy, disused part of Toronto into a spectacular public park, an art gallery, a performing arts venue, a skating trail, and so much more. Ilana Altman, the organization's CEO, is an ambitious, visionary leader, who also happens to be a rather lovely person. This is a fantastic opportunity.Ben Leszcz shared thisWe’re hiring! The Bentway is looking for a Director of Marketing & Communications to join our leadership team and help tell the story of what public space can make possible. We’re looking for a strategic, creative communications leader who can build audiences, deepen our connections, and expand our impact. Know someone who should be part of the next chapter of The Bentway? Apply by September 30: https://lnkd.in/gqKW6ysq
-
Ben Leszcz reposted thisBen Leszcz reposted thisI need the help of my brilliant LinkedIn network. We’re looking for THREE new Trustees to join Institute of Imagination Being a Trustee of iOi has been one of the most meaningful roles I’ve had. I’ve had the privilege of getting close to the work and the team over the years, seeing children and families who don’t always have access to creative opportunities discover what happens when they’re given permission, space and tools to imagine, make, play and explore. And I’ve seen the ambition behind it: not simply to deliver brilliant experiences for children, but to ask how we can make imagination and creativity a much bigger part of childhood and education across the UK. That feels increasingly urgent to me. Our children are growing up amid extraordinary technological, social and environmental change. We cannot know exactly what world we are preparing them for. But we can help them develop the confidence to imagine what doesn’t yet exist, question what they’re given, create with others and believe they have agency in shaping the future. Now iOi is entering its next chapter, and we’re looking for three new Trustees to help shape it. So I’m asking my network personally: who are the people we should be talking to? Who brings a perspective we might not already have? Who deeply understands children, education, creativity or systems change? Who would challenge us, open doors and help us think bigger? Please tag them, send this to them, or put yourself forward. And if you’re curious about what being a Trustee is really like, message me - I’d be very happy to share my experience. Help us find three brilliant humans for this next chapter. ❤️ https://lnkd.in/eR7Uazyb
-
Ben Leszcz reposted thisBen Leszcz reposted thisMatt Cohen and I are very excited to announce that Ripple Ventures Fund IV is now live, anchored by Northleaf Capital Partners, RBC / RBCx, and one of Canada's largest private conglomerates. The firm I walked into and the firm we run today are not the same one, and every bit of that change has been in the right direction. Sharper focus, bigger swings, and higher standards for ourselves. Fund IV marks the start of a new arc for Ripple, and we already have ten companies in the portfolio. Three things are guiding this fund: - Following the brightest founders into the most ambitious things being built. - Investing with conviction in the earliest stages (pre-product and pre-traction). - Supporting sovereign capabilities with frontier technologies. Welcoming the newest portfolio companies out of this fund: Canada Rocket Company: Hugh Kolias and David Tenny North Vector Dynamics: Paul Ziadé, Craig Johansen, and Colin Hill Terranox AI (YC W26): Jade Checlair and Leeav Lipton Daedal Systems: W. Henry Gould, P. Eng. Valen: Rohit Rustagi and Ibrahim Abusharkh Green Abundance: Celeste Holz-Schietinger uRun: Keegan McCallum Silmo: Dustin Z., Adrien Morisot, and Rodrigue Hajjar Blackletter: Jonathan Rosenbluth, David Stewart, and Avi Brudner Asset: Cameron Frayne and Alejandro Mesa To the founders we have not met yet: if you are building with this level of ambition, we'd love to partner with you. The full story is in Matt's post in the comments section and our launch video below.
-
Ben Leszcz reposted thisBen Leszcz reposted thisCalling all Toronto booksellers and bartenders! We're growing our team at Book Bar and are looking for passionate, welcoming people who love books, hospitality, and building community. Think you'd be a great fit? We'd love to hear from you. Apply below or share this with someone who should! https://lnkd.in/gSaKDke2BookBar Canada Holdings Corporation Jobs & Careers | Employment HeroBookBar Canada Holdings Corporation Jobs & Careers | Employment Hero
-
Ben Leszcz shared thisA great insight—and an incredible offer for founders raising a round.Ben Leszcz shared thisEvery February, the world's best baseball players head south for weeks of games that don't count. As Sandy Koufax said, "People who write about spring training not being necessary have never tried to throw a baseball." Fundraising is similar. Rehearse all you want, but nothing truly prepares you like the real thing. Raising Blackletter's round reinforced a lesson that Koufax knew well: Your first pitches will not be your strongest. That's why my advice to founders is to plan a kind of VC spring training: Don't open with the investors at the top of your list. Seasoned investors will poke holes. They will ask hard questions. And you will almost certainly walk out of the room wishing you'd said something different. Use it all as intel. Tighten your pitch. Iron out the kinks. There's risk here, of course: investors use Granola and share notes. Your early reps might not stay secret. I'd rather have my best stuff by the time the games really count. We learned from every raise at Cohere, and from running our own at Blackletter. We're eager to share those lessons. That's why we're inviting founders raising a round to use us as a thought partner -- on legal advice, but also on fundraising strategy. If that's you, reach out. I'd love to chat.
-
Ben Leszcz shared thisLove this take from our Blackletter client, Jonathan Rosenbluth. It's 2026. If your goal is to provide clients—in any business—with the best possible service and outcomes, *not* integrating AI into your workflow is downright negligent.Ben Leszcz shared thisI'll confess: I have called Blackletter an AI-native law firm. But I've come to hate this description. It's a useful shorthand. AI-native services are the darling of the VC world right now. And AI is integral to how we work -- and to how we differentiate. But "AI-native" says nothing about the value that we actually bring to clients. When people hear it, they think fast and cheap. At Blackletter, we're building an elite law firm that can be trusted with complex, high-stakes matters. And because it's 2026, we use technology to do it. It would be foolish, if not negligent, not to. Our clients tell us the same thing. We don't hear about the tech; we hear about the relief of partnering with a firm that understands how businesses -- and especially startups and investors -- actually function. In a couple years, AI-native law firms will have a new title: law firms. At that point they'll be differentiated by two things -- the quality of their people, and the quality of their technology. So we're building both. The best lawyers we can hire, and technology other firms can't buy off the shelf. Not for the label. For the client experience. No prefix required.
-
Ben Leszcz reposted thisBen Leszcz reposted thisVertiq Hospitality Partners is delighted to announce exciting pre-opening career opportunities for the upcoming Autograph Collection Resort at Quinta do Mar – Sintra, an exceptional addition to the Marriott portfolio. Nestled within the breathtaking UNESCO World Heritage landscape of Sintra on Portugal's dramatic Atlantic coastline, this luxurious 89-bedroom resort is set to deliver a distinctive luxury hospitality experience, combining authentic destination-led experiences with world-class service. As we prepare to bring this remarkable property to life, we are seeking experienced hospitality professionals to join our pre-opening leadership team in the following roles: ✨ Director of Sales & Marketing (Pre-Opening) ✨ People & Culture Manager (Pre-Opening) ✨ Operations Manager (Pre-Opening) These are unique opportunities to play a pivotal role in shaping the culture, guest experience, commercial success, and operational excellence of one of Portugal's most anticipated luxury resort openings. If you are passionate about luxury hospitality, thrive in pre-opening environments, and are ready to leave your mark on an exceptional destination, we'd love to hear from you. Apply today or connect with our team to learn more - https://lnkd.in/euBcYkye #VertiqHospitalityPartners #HospitalityCareers #LuxuryHospitality #Marriott #AutographCollection #PreOpening #DirectorOfSales #PeopleAndCulture #OperationsManager #LeadershipCareers #PortugalJobs #Sintra #HospitalityLeadership #Recruitment
-
Ben Leszcz reposted thisBen Leszcz reposted this🚨 Hiring Alert We’re building a new AI-native venture for the investment banking industry. By embedding AI across the deal lifecycle, we’re enabling advisory teams serve more clients, work more efficiently, and deliver better outcomes. If you, or someone you know is a seasoned CEO or banker looking for their next challenge and is interested in co-founding a new startup, we’d love to hear from you. 📩 Key contact: Justin Corbishley Learn more and apply: https://lnkd.in/gDcwAyuP #Diagram #Fintech #InvestmentBanking #M&A
-
Ben Leszcz liked thisBen Leszcz liked thisMeet, Boobet! A can that gives back 100%, so we leaned in 100%. This limited-edition Barbet Love Bite can is all dressed up to support Rethink Breast Cancer in a bigger way. As part of our ongoing giveback program, we already donate 1% of Love Bite sales to Rethink, but as part of their 25th-year celebrations and Breast Cancer Awareness Month, we wanted to do more. Boobet gives back 100% of proceeds to Rethink Breast Cancer. With 100% of proceeds going to Rethink, we wanted to lean all the way in with our design. So, we subbed out Barbet for Boobet. A big thank you to the team at No Fixed Address Inc. for the design! Gabriella Monika Alison Logan Annie MJ Want to support Rethink? Grab a can online -> https://lnkd.in/ggBs7HPp Check out Rethink House Events -> https://lnkd.in/g7aXPJfz Get a ticket to Boobyball -> https://lnkd.in/gm-3hvj6 Shop the 25 for 25 -> https://lnkd.in/gdtX6hcq Hosting an event in support of Breast Cancer Awareness Month this October? Grab some Boobets or one of the other 25 for 25 products for it! Shoutout to some of the other incredible founders and brands giving back in a big way: Jenny Bird Amanda Santino Laura Santino Erin Kleinberg Lisa Gozlan Drummond Munro Carlo Colacci Tara Miller
-
Ben Leszcz liked thisBen Leszcz liked thisThe first time I spoke with David Stewart, he asked me something no one had asked before: "How does your API handle reconciliation of multiple conflicting edits?" David Stewart is the CTO of Blackletter, a new kind of law firm built from first principles around client needs and frontier technology. Blackletter launched this summer with fixed prices, no billable hours, and elite lawyers, and has since grown rapidly. Before we spoke, David had already created test API keys via our self-serve developer portal and spiked integration of our infrastructure for comparing legal documents. His testing had confirmed the table stakes: that our deterministic comparison engine met the high standards of his lawyers. "Version Story was quick to integrate, and our lawyers were impressed with the quality of the redlines," David later told me. "It stood out from the other solutions we evaluated." He had spent the previous month paying for the incumbent’s redlining product while his team waited for licenses that never arrived. His API request there had gone unanswered for six weeks. Now, on our call, he wanted to drill into how our infrastructure could support his multi-agent workflows. As David grilled us on the finer points of document comparison and versioning, I felt pure excitement. When we joined Y Combinator in January 2021, our tagline was "git for lawyers." In the long march that followed — the years we worked on designing our algorithms and building out support for the tens of thousands of edge cases our engine needed to handle for lawyers to trust our comparisons — our north star was the conviction that one day software engineers like David would find their way into the legal profession. We built Version Story in the belief that technology would inevitably transform the legal profession. Now that AI has catalyzed that shift, we’re thrilled to be able to support the builders and visionaries who are reshaping the industry. Onboarding new customers feels like handing over the keys to a beautiful house we spent years building. Do you do PDF to DOCX comparison? Yup. What about creating a history of changes across multiple versions? Yes, also that. And so on. Since our last call with David, Blackletter has scaled to running thousands of comparisons via our API each day. When we told him over Slack that we’d pushed an update bringing comparison latency to under one second, he replied with a thumbs-up emoji. We’re planning to hop on another call with David when we’ve rolled out our upcoming DOCX editing APIs for him to test.
-
Ben Leszcz liked thisBen Leszcz liked thisMontford Group is growing, and we're excited to welcome Mac Clark to the Investments team as an Associate. Mac's work centers on sourcing and underwriting new hotel acquisition opportunities — digging into valuations, navigating capital markets, and building the broker relationships that keep our pipeline strong. Before joining us, Mac spent two years at MetLife Investment Management, gaining experience on both the debt and asset management sides of commercial real estate — exposure that gives him a well-rounded view of a deal from every angle. He's a 2024 Villanova School of Business grad and outside the office he's just as competitive on a run or a golf course as he is in a deal room. We're glad to have him on board. Welcome, Mac!
-
Ben Leszcz liked thisBen Leszcz liked thisI love magazine fairs! I love them so much that I decided to organize one. Inspired by the amazing Food in Print fair, Tasting Notes will be bringing together 25+ food-focused magazine publishers and book stores. Our friends at Caper will be onsite, curating a selection of food books, and running a panel discussion covering the latest in taste, hospitality, and fashion. A huge thank you to the amazing team Iconic and Casa Magazines | Global News Inc. who have stepped in to support us. Where: The Lighthouse, 58 Kent St. Brooklyn When: October 17th, 11am - 6pm Photo Credit: Vicky Lam Stylist: Dee Connolly
-
Ben Leszcz liked thisBen Leszcz liked thisThank you, Hotel Business Magazine, for covering our rebrand to Montford Group! Same team, same company, just a new name. https://bit.ly/3TxdKXKTMGOC Ventures rebrands as Montford Group - hotelbusiness.comTMGOC Ventures rebrands as Montford Group - hotelbusiness.com
-
Ben Leszcz liked thisToday we rebranded TMGOC Ventures as Montford Group. A new name, but the same people and the same commitment to our partners. Sunju Patel and I are incredibly excited about the road ahead, and grateful to everyone who helped us get here.Ben Leszcz liked thisIntroducing Montford Group. Built on the foundation of TMGOC Ventures, Montford Group represents the next evolution of our investment platform. A new identity. An expanded vision. The same disciplined approach to investing and creating long-term value alongside our partners. Montford Group Entrepreneurial by nature. Institutional by design. Read the article here: https://lnkd.in/e3mcQ_4m Glenn Alba Sunju PatelTMGOC VENTURES REBRANDS AS MONTFORD GROUP, MARKING THE NEXT CHAPTER FOR THE $1.5 BILLION REAL ESTATE INVESTMENT PLATFORMTMGOC VENTURES REBRANDS AS MONTFORD GROUP, MARKING THE NEXT CHAPTER FOR THE $1.5 BILLION REAL ESTATE INVESTMENT PLATFORM
Experience & Education
Volunteer Experience
-
Strategy Consultant/Committee Member
The Bentway
- Present 7 years
Arts and Culture
I serve as an informal strategic advisor to the executive directors. In 2020/21, I worked closely with them to define the strategy and mission of the Bentway. I also sit on the marketing/communications committee.
-
Director
Cycle Toronto
- 3 years 1 month
Environment
As a director of Cycle Toronto, I led the initiative to refresh the organization's strategic plan, with focus on its mission, vision, values and strategic objectives.
-
Chair, Community Kitchen
Friends of Roxton Road Parks
- 5 years 1 month
Social Services
As a member of Friends of Roxton Road Parks, I worked with my neighbours to support the vitality and accessibility of three local parks. I also helped develop the vision for the community kitchen.
Languages
-
French
-
Recommendations received
1 person has recommended Ben
Join now to viewOther similar profiles
Explore more posts
-
Rachel Thexton
One of the topics I discussed with Lynda Steele, on the season #7 debut podcast episode, is the state of Canadian media, its future, and how traditional journalism can survive in the digital age, when some of the trust in media has eroded. Lynda has some ideas and perspectives worth hearing. Sample clip, and link to full episode, below. https://lnkd.in/gBJ-J9ry
-
Abby McIntyre
This report is worth reading for what it shows beneath the AI headlines. And yes, this is US data, but the pattern tracks with what many of us are seeing in Canada and across public-serving organizations. Nearly 50% of CEOs say traditional communications skills will become secondary to AI fluency. With 96% of organizations already using AI in their communications work, that reaction makes sense. But here’s the part that matters. The same CEOs rank strategic thinking, problem solving, and staying calm under pressure as the most valuable skills for communications leaders. That isn’t a contradiction. It’s a signal. Tactical work is being automated. What leaders want now is clarity, alignment, and judgment. The work that helps an organization understand what problem they’re solving, what decision they’re making, and how to move forward when things get difficult. If we keep defining communications as tasks, AI will win. If we define it as strategy in action, this becomes a moment to lead. AI didn’t erase the value of communications. It exposed the shallow version. https://lnkd.in/e6gExJgC Ragan Communications and PR Daily
-
Robert Pickard
It is truly remarkable how many CEOs think that they are public relations experts — while demonstrating the exact opposite. The belief that silence somehow reduces reputational risk is one of the most persistent and costly myths in leadership communication. Here’s the latest example in the news this week: “When one employee asked what he should say in response to customer enquiries or negative feedback to the ICE deal on social media [Hootsuite CEO] Irina Novoselsky said that engaging publicly was not the right thing to do. ‘There’s no winning here,’ she replied. ‘If we go and answer it, there will just be more news cycles.’ Engaging with the issue, she added, ‘won’t change the narrative.’” Narratives do not automatically dissipate in the absence of engagement, but they often do compound or even metastasize. By refusing to respond, leaders delegate meaning-making to critics or skeptics, ensuring that the most damaging interpretations dominate. A CEO explaining a communications avoidance strategy publicly only entrenches the error. That’s because it proves engagement is unavoidable while signaling an inability to stand behind the substance of a corporate decision. This is not about ‘feeding the media cycle.’ It is about whether leadership retains authorship of its own story — or forfeits it by making wrong-headed assumptions. Either the Hootsuite CEO is getting bad PR counsel or isn’t following good comms advice. https://lnkd.in/gTWCxpcA #LeadershipCommunication
21 Comments
Explore collaborative articles
We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
Explore More