Shows
CRAFTED.We're Still in AI's “Fart App” Era… And Other Deep Thoughts from SXSW, With Rob KenediOn a rooftop at SXSW, fellow startup advisor and podcaster Rob Kenedi joins me as we discuss why: AI models are becoming commodities…AI companies need to differentiate at the application layer, with brand, and by earning trust…B2B creators are all the ragePodcasts are so intimate and how video changes thingsWe’re in the “fart app” era of AI…Enjoy this uncrafted CRAFTED.!And if you enjoy this more casual format, please share your feedback. DM me on LinkedIn or email me: dan@modernproductminds.comWhere to find...2025-04-1016 min
The BetaKit Podcast ChannelMama don't take my Google Chrome away“Browsers aren't a business. Browsers don't make money. These are loss leaders for other connected experiences because no one wants to pay for the window to the web." The DOJ wants to take Chrome away from Google. Arc wants to build a better browser for everyone. Rob Kenedi wants to decelerate tech with his new show, which is not (yet) a browser. Let’s dig in. The BetaKit Podcast is brought to you by Cloudways, the managed hosting platform built for speed and scalability. Take advantage of Cloudways Black Friday Cyber Monday offer: 40% off for 4 mont...2024-12-0151 min
Helpful PodcastRob Kenedi - Don't Help Like MobstersRob Kenedi understands the power of being genuinely helpful. He knows when you go out of your way to assist others, it comes back to you in unexpected ways.
He was responsible for setting up Canada's 911 infrastructure. He didn't leave their implementation partner to fend for themselves. He took it upon himself to assist, working late, often into the morning. He didn't know this act of kindness would build a lasting connection, and significant revenue 15yrs later.
He also shares energy management by finding a balance between others' needs and your own, and making decisions based on intuition.
The...2023-10-2718 min
The BetaKit Podcast ChannelWhy I killed my startup"It's not like a light comes down from heaven and says 'now you shall stop your company.' But, man, was it very difficult emotionally." Entrepreneur and BetaKit Podcast co-host Rob Kenedi explains the process of launching and eventually shuttering his startup, Staid.2023-02-0348 min
The BetaKit Podcast ChannelUkraine, soonicorns, Canadian tech vibe check (AMA episode)"What is your vibe right now about Canadian tech?" Co-hosts Douglas Soltys and Rob Kenedi are joined by BetaKit associate editor Meagan Simpson to answer listener questions submitted LIVE during a special Twitter Spaces AMA edition of the BetaKit Podcast. Sponsored by Pocketed.2022-03-031h 12
The BetaKit Podcast ChannelShopify's crypto bros, and anti-growth is cool now (AMA episode)"This is a Web3 podcast now." Co-hosts Douglas Soltys and Rob Kenedi are joined by producer Kattie Laur and BetaKit associate editor Meagan Simpson to answer listener questions about the 'anti-growth' movement, Shopify's blockchain team, and what's holding #CDNtech back. Sponsored by SVB and Innovate BC.2021-11-1241 min
The BetaKit Podcast ChannelTekSavvy's pissed and Shopify's a FinTech (AMA episode)"Are you looking for a reprieve from the summer heat or do you want a hot pod summer?" Co-hosts Douglas Soltys and Rob Kenedi are joined by producer Kattie Laur to answer listener questions about whether the election killed open banking, why TekSavvy's pissed and the CRTC doesn't seem to care, and when it's time to start ignoring Shopify announcements. Sponsored by VanHack. Produced with support from TWG.2021-08-2857 min
The BetaKit Podcast ChannelWhen will Canadian tech stop paying peanuts? (AMA episode)"Can we expect that Canadian tech will start paying talent what they're worth?" Co-hosts Douglas Soltys and Rob Kenedi are joined by producer Kattie Laur to answer listener questions about US companies nabbing Canadian talent; under-the-radar unicorns, what's happening in cleantech and healthtech; and employee mental health. Sponsored by Nugget.ai. Produced with support from TWG.2021-06-2647 min
The BetaKit Podcast ChannelWill Canadian tech regret the move to remote-first? (AMA episode) | Black Swan #45"I will eat my shirt if they don't." In celebration (?) of one year of Black Swan, co-hosts Douglas Soltys and Rob Kenedi are joined by producer Kattie Laur to answer listener questions and reflect on what's been learned from a COVID-focused podcast. Sponsored by Cisco Designed. Produced with support from TWG.2021-03-2654 min
The BetaKit Podcast ChannelBlack Swan #1 - How to Survive"Everything that happened over a four to five-month period in '08 has happened in a four-week period this time around." The Canadian tech ecosystem is facing a black swan event: extremely rare and extremely severe. BetaKit spoke with Matt Roberts, partner at ScaleUP Ventures, about the federal government's response to support Canadian businesses, and what entrepreneurs can do to ensure their companies survive. Hosted by Douglas Soltys & Rob Kenedi. Edited by Kattie Laur. Produced with support from TWG.2020-03-3040 min
Entrepreneurs in Small Rooms Drinking CoffeeMichael Kousaie - TSXRob Kenedi sits down for a coffee with Michael Kousaie, Head of Technology Business Development for the Toronto Stock Exchange and the TSX Venture Exchange. Kousaie, discusses not only the traditional path to going pubilc and how the TSX helps companies get there, but also focuses on the venture exchange as an alternate path to raising capital around the series A and B timeframe. Kenedi digs deeply into the mindset of investors on the venture exchange and their expectations, how entrepreneurs know if it is the right path for them, and how he thinks of the path to IPO with...2017-03-1043 minEntrepreneurs in Small Rooms Drinking CoffeeMatt Leibowitz | Plaza VenturesRob Kenedi has a coffee with Matthew Liebowitz, partner at Plaza Ventures. Matthew talks about their approach to growth investing at Series A enterprise-focused SaaS startups, the fact that the fund is always raising capital rather than in huge lump sums, the fact that the partners are compensated only on performance of the portfolio, and what failure looks like when investing into this later phase of a startup's development.2017-02-1048 minEntrepreneurs in Small Rooms Drinking CoffeeMeta | Acquired by Chan Zuckerberg InitiativeIn this special retrospective recorded 1 year ago, Rob Kenedi speaks with Sam Molyneux, founder of Meta(at the time known as ScienceScape). Meta is a startup that uses machine learning to look at all of the journals being published in science to uncover emerging discoveries and anticipate their impact ahead of time. The Chan Zuckerberg Initiative just acquired them last week.
Full disclosure: Meta is a client of TWG, where Rob Kenedi serves as Entrepreneur in Residence.
Sam discusses the key use cases of Meta, why he (as a scientist) saw the need to build a company, how they think...2017-01-2836 minEntrepreneurs in Small Rooms Drinking CoffeeVM FarmsRob Kenedi chats with Hany Fahim, founder of VM Farms, a devops as a service startup, which helps companies focus on developing software rather than managing it.
Fahim discusses his decision to bootstrap rather than look for external financing, how to price his product against Amazon, when to hire a sales person, and a play-by-play of how the team found product/market fit.2017-01-1335 minEntrepreneurs in Small Rooms Drinking CoffeeSutoHost Rob Kenedi has a coffee with Nima Gardideh of Suto, an SMS-based bot that recommends the best product to buy.
Gardideh has just pivoted away from this particular business and describes how it worked and why it made sense to move on. He also discusses what he had learned from Venio, an Extreme Startups cohort member and his first startup, and how to wind one down with employees and investors. Gardideh also describes being a product manager at very successful Canadian startups Frank + Oak and Taplytics, and how he applied all of those learnings to his venture while he...2017-01-0636 minEntrepreneurs in Small Rooms Drinking CoffeeSnapTravelRob Kenedi sits down with Hussein Fazal, founder SnapTravel, a SMS, Slack and Facebook Messenger bot-based hotel booking service. Hussein discusses how and when he decided to sell his last startup, AdParlor, and how he is approaching latest endeavour. In particular, he describes how to navigate a hot, new space that hasn't yet found well-understood user experience as well as the how to solve for the imperfect science of natural language processing and machine learning.2016-12-2244 min
The BetaKit Podcast ChannelCanCon Podcast Ep. 43: Canada at Web Summit and video games have changed, manRob Kenedi returns as the CanCon team discusses his travels to Web Summit and the weird state of video games. 2016-11-2246 minEntrepreneurs in Small Rooms Drinking CoffeeDaisy IntelligenceRob Kenedi a coffee with Gary Saarenvirta, founder of Daisy Intelligence, a business insights tool based on artificial intelligence.
Gary discusses successfully bootstrapping his company based on his experience by first building a services company, what is not artificial intelligence, and how to rationally grow a business while competing with companies such as IBM.2016-09-1535 minEntrepreneurs in Small Rooms Drinking CoffeeHumiRob Kenedi has yet another coffee with Kevin Kliman, founder of his latest venture, Humi, a free, all-in-one HR cloud-based platform. In a first for #smallrooms, a former guest returns as the founder of his latest venture. Kevin describes what he learned from his last startup, Instaradio / Raur, and how he approached creating his next startup, taking his lessons from the accelerators he had been part of, including 500 Startups and Amplify, his position on obtaining funding the second time around, and his thoughts on how to break into a heavily regulated, relationship-based market.2016-09-0244 minEntrepreneurs in Small Rooms Drinking CoffeeGatsbyOn a special version of Entrepreneurs in Small Rooms Drinking Coffee, the #smallrooms team recorded episodes live at StartupFest 2016 in Montreal.
Rob Kenedi chats with Aaron Jun of Gatsby, a event planning solution for groups. Aaron focuses on messaging as a user interface and getting out of beta.2016-07-2332 minEntrepreneurs in Small Rooms Drinking CoffeeFans UniteOn a special version of Entrepreneurs in Small Rooms Drinking Coffee, the #smallrooms team recorded episodes live at StartupFest 2016 in Montreal.
Rob Kenedi chats with Darius Eghdami of Fans Unite, a fantasy sports betting platform that enables handicapping in real life. Darius discusses getting investment in the gambling space and solving the engagement and retention problem.2016-07-2332 minEntrepreneurs in Small Rooms Drinking CoffeeParlayOn a special version of Entrepreneurs in Small Rooms Drinking Coffee, the #smallrooms team recorded episodes live at StartupFest 2016 in Montreal.
Rob Kenedi chats with Bobby McDonald of Parlay, a student engagement education platform, on when his platform is "done" enough to launch, and how to structure a pilot.2016-07-2331 minEntrepreneurs in Small Rooms Drinking CoffeeHelloMDOn a special version of Entrepreneurs in Small Rooms Drinking Coffee, the #smallrooms team recorded episodes live at StartupFest 2016 in Montreal.
Rob Kenedi chats with the StartupFest investment prize winner, Pamela Hadfield of San Francisco-based HelloMD, a medical marijuana referral service and support network. Pamela discusses building a business when one cannot use traditional advertising to acquire customers.2016-07-2335 minEntrepreneurs in Small Rooms Drinking CoffeeDaniel Klass | Klass CapitalRob Kenedi has a coffee with Daniel Klass, managing partner of Klass Capital. Daniel details his non-standard approach to investment, including not co-investing with other funds, acquiring companies to grow them further, the avoidance of a specific thesis or limitations in geography, and the reason why it makes sense for an entrepreneur to partner with an investor to attain a significant portion of a company.2016-06-3048 minEntrepreneurs in Small Rooms Drinking CoffeeBorrowellRob Kenedi shares a coffee with Andrew Graham, founder of Borrowell, a marketplace lending platform. Andrew and Rob discuss why Borrowell does not do peer-to-peer lending, how they got their initial capital to lend, and how he thinks about potential competitors in the existing financial marketplace.2016-06-2345 minEntrepreneurs in Small Rooms Drinking CoffeeSam Ifergan | iGan PartnersRob Kenedi sits down with Sam Ifergan, managing partner of iGan Partners & Rowanwood Ventures. Sam discusses iGan's multiple forms of investment - syndicate and early stage venture capital, their focus on B2B businesses, especially SaaS, as well as medical devices and healthcare IT. Sam details iGan's focus on early stage companies and how he believes the iGan model is superior to simply raising angel investment, his rationale for focusing only in Ontario, and how his history colours his team's choices in the startups they choose to partner with.2016-06-1654 minEntrepreneurs in Small Rooms Drinking CoffeeBrice Scheschuk | Globalive CapitalRob Kenedi has a coffee with Brice Scheschuk, CEO of Globalive Capital and co-founder of Wind Mobile. Brice details the history of Globalive, including what it was like to start Wind against a strong set of mobile competitors and then ultimately sell the company, and as an investor, their unique position to invest in both startups directly and indirectly via investors, including many notable Canadian funds. Brice also details a unique perspective on Canadian startups and details an articulate counter-narrative to what success looks like for a Canadian startup.2016-06-0957 minEntrepreneurs in Small Rooms Drinking CoffeeJane Podbelskaya | Georgian PartnersRob Kenedi chats with Jane Podbelskaya, senior associate at Georgian Partners. Jane describes Georgian Partners' thesis-driven, unique hands-on approach to later stage startup investment in such notable companies as Shopify, Freshbooks, Top Hat and Vision Critical. Jane details how Georgian does its due diligence on startups they invest in, patterns she's seen once they get under the hood, and how the team thinks about new, hot spaces such as chat bots and conversational commerce.
Disclosure: Freshbooks and Shopify are clients of TWG, where Rob serves as Entrepreneur in Residence.2016-06-0245 minEntrepreneurs in Small Rooms Drinking CoffeeUnata RevisitedRob Kenedi sits down again with Chris Bryson, founder of Unata, a grocery/retail-focused startup that creates personalized experiences for shoppers. Chris and Rob follow up their pre-traction discussion from 2014 to better understand how Unata's non-venture backed company has succeeded and navigated its rapid growth. Chris reflects on how to find focus in a big, nebulous space, how to manage multiple customers' feedback once product/market fit is achieved, and how to get your second customer.2016-05-2142 minEntrepreneurs in Small Rooms Drinking CoffeeAndrew PeekRob Kenedi sits down with Andrew Peek, founder of Pilot, a note-taking startup scooped up alongside Jet Cooper when it was acquired by Shopify, who describes his strategy to start his next company. Andrew recounts his startup experience while building a product company within a services company, some product decisions that he would have made differently in retrospect, and how too much funding made his experience trickier than one would expect. Having left Shopify post acquisition, Andrew describes his hard-earned rigour around creating his next venture and the process by which he decided to pursue the startup.2016-05-0648 minEntrepreneurs in Small Rooms Drinking CoffeeTab RevisitedRob Kenedi once again has a coffee with Adam Epstein, founder of Tab, a restaurant payment and reservation system, recently acquired by Velocity. Rob and Adam chat about the difficulty raising capital in the Valley, managing interest from potential acquirers, and figuring out how to sell your startup and all the complications therein.2016-04-2149 minEntrepreneurs in Small Rooms Drinking CoffeeWealthsimple RevisitedRob Kenedi sits down again with with Michael Katchen, founder of Wealthsimple, an automated investment manager for consumers. Rob and Michael discuss building trust with your customer in a trust-based business, scaling a company when you get a rapid $30 million Series A, and how to combat sizeable competitors in the financial industry.
In the revisited series of #smallrooms, Rob reconnects with the startup to see what's happened since the last episode (typically a year later). For the full narrative, check out the previous episode with Michael pre-Series A and their explosive growth from February of 2015.
DISCLOSURE: Wealthsimple is currently a...2016-04-1444 minEntrepreneurs in Small Rooms Drinking CoffeeFour WallsRob Kenedi speaks with Michael Van, founder of Four Walls, a startup that enables consumers and small businesses to buy fully furnished rooms with one click on the web. Michael and Rob discuss Four Walls' experience in an pre-accelerator, Techstars Startup Next, starting down a consumer path to get to market but why going after small and medium sized businesses made more sense, and their decision not to raise capital at all.2016-04-0838 minEntrepreneurs in Small Rooms Drinking CoffeeBig TerminalRob Kenedi talks to Adam Rabie, a big data fintech platform that uses machine learning to sort and filter the news to help investors make better decisions. Adam and Rob chat about finding the need for his startup while working at a corporate job, finding his first investor, figuring out when to actually ship your first product, and his take on freshly looking for funding in what may be a down market.2016-03-1842 minEntrepreneurs in Small Rooms Drinking CoffeeRoger Chabra | Rho VenturesRob Kenedi has a coffee with Roger Chabra of Rho Canada Ventures, an entrepreneur turned investor who discusses his views on investing in Canada versus the Valley, what value a VC adds to the startup and how to pick one and candid insight regarding how his team considers working with seed and early stage technology companies.2016-03-1054 minEntrepreneurs in Small Rooms Drinking CoffeeStackAdaptRob Kenedi speaks with Vitaly Pecherskiy of StackAdapt, a branded content native advertising platform. Fresh of their Series A, Vitaly explains how the team bootstrapped their way to finding a product, getting a $1 million seed followed shortly thereafter by a $1 million Series A and balancing HR as product-market fit is being discovered.2016-02-0437 min
The BetaKit Podcast ChannelCanCon Podcast Ep. 1: Hipster TV and our dollar sucksOn the first ever edition of the CanCon Podcast, Douglas Soltys, Erin Bury, Rob Kenedi, and Patrick O'Rourke discuss Netlfix, Showmi, CraveTV, and VR. Music clip: “Money City Maniacs” by Sloan2016-01-251h 03Entrepreneurs in Small Rooms Drinking CoffeeNicole VerkindtIn this episode, the first #smallrooms Investor Edition, Rob Kenedi sits down with Nicole Verkindt, founder of the OMX and angel investor via CBC's Next Gen Den, a tech-focused version of Dragon's Den. Nicole reflects on being an early stage angel investor after being a founder, how she navigates hundreds of pitches on TV and what happens behind the scenes, and how that has affected her investment thesis.2016-01-2238 min