Rob Kenedi
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Fractional Startup Leader | Founder | Podcast Host | Future Top 90 under 90
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Articles by Rob Kenedi
Connor Gaydos Bought Enron to Fix America's Energy Crisis - Consensus 2025
🔊 Subscribe: YouTube | Apple Podcasts | Spotify New Episode: Enron At the Consensus 2025 conference in Toronto, I discovered something unexpected: Enron - yes that Enron - the infamous energy company that collapsed in 2001 is being revitalized with a mission to solve America's energy crisis.
Being helpful, the mob, & being in charge of 911
Welcome to post-time change November! Why this anachronism hasn't left us yet is beyond me, killing and maiming , reducing our carbon footprint, and making us all grumpy. Maybe my offer below is more relevant than I'd suspected... read on! Anyhoo, I had the privilege of being on the inaugural season of my friend Vahid Jozi's new podcast Helpful, focusing on stories of how being helpful can make an impact.
Hugging Face’s Sasha Luccioni on tracking the ethical and environmental impacts of AI
While Douglas Soltys was moderating panels the on AI stage at Elevate (which BetaKit programmed), I was in Montréal at ALL IN, the inaugural AI conference hosted by Scale AI.
Entrepreneurship & Mental Health
Nov 29, 2022 1 min I suffer from anxiety and depression. It kinda fucking sucks. Interestingly, it's not something I was forthcoming about in my youth since it was stigmatized and is still not exactly accepted. I still get the "cheer up" or "just try harder" from time to time, which does surprise me. Also, I naively assumed that as you age, it just gets better, but ... I think I just get better at noticing the signs of when it happens and then, well, just dig in and cope (how Gen X of me).
How has the tech downturn affected founder mental health?
Nervous founders. Nervous investors. Nervous… everyone. Tech winter. Nervous founders. Nervous investors. Nervous… everyone. Talk about a change of pace. What’s the effect on entrepreneurs’ mental health? Let’s find out. Douglas is out this week so it’s just me, speaking again with Dr. Michael Freeman, founder of Econa, a global center of excellence for entrepreneur mental wellness based out of San Francisco.
It's always the simple things
Listening to a few (very different) podcasts and working on Staid over the last couple of weeks got me thinking about why we do what we do. And if you boil it down, it's really not all that complex. See if you agree with me. First, let's start with one of the best podcast episodes I've heard in years. It's truly insightful and fascinating. My thought process for this post started here, but the episode is so good, it's straight up worth a listen.
How do you measure culture in the remote and hybrid workplace?
Donuts are not enough. Let’s face it: building culture is hard. And in this now-familiar “new normal,” it’s really, really hard. So how do companies do it? And equally as important, how do they measure it? As we settle into a more clear understanding of what a modern workplace looks like, we wanted to look deep into the heart of the Canadian startup ecosystem and get some real-time data. How are companies faring in their attempts to build hybrid or remote work culture?
What can the metaverse learn from accessibility leaders?
As the neverending work from home march continues, we’ve seen our society reconfigure itself physically and virtually to live with the pandemic. From lousy virtual networking events to tables in restaurants that have become spaced out for health reasons having the side effect of allowing people with wheelchairs to more easily navigate physical spaces.
How COVID-19 changed Canada's biotech sector
Canada’s biotech sector has been exploding, with good reason given the events of the last year. “Innovation and biotechnology was the star of the day.” The sector has become so significant that it also received a spotlight in the recent federal budget.
What Canada's healthcare system learned from the pandemic
Regular listeners of the Black Swan podcast know that its focus is on the entire Canadian innovation ecosystem, from startups and enterprises to policy and pivots. Having tracked the collision of healthcare, technology, and the Black Swan version of normal in 2020, we thought we’d unpack what we can expect for Canadian healthcare in 2021.
#smallrooms Podcast: Dan Holowack of CrowdRiff on visual marketing
Rob Kenedi sits down with Dan Holowack?, founder of CrowdRiff, a visual marketing platform that intelligently sources images from across the Internet, including social media. Holowack discusses bootstrapping for a long time before seeking funding, why they sought funding, when to say no to prospects, and truly evaluating what was their MVP. He also discusses how to evaluate “analytics as a business model” and how they discovered their niche and business model, including pricing.
#smallrooms Podcast: Nick Corneil of Trainer+ on the Fitness Market
Rob Kenedi has a coffee with Nick Corneil, co-founder of Trainer+, a platform for fitness history and planning for trainers and gyms. Corneil reflects on his prior experience in the startup Venio, and how that affected his approach to this venture, how he validated his initial product, and how he dealt with parting with one founder and adding another.
#smallrooms Podcast: Matt Roberts of ScaleUP Ventures on Early-Stage Investing
Rob Kenedi goes for a coffee with Matthew Roberts, partner at ScaleUP Ventures. Roberts explains ScaleUP’s value proposition to entrepreneurs, including the fact that the partners have significant startup operational experience. Roberts also discusses the mechanics of the fund, the patterns he has seen over many years of investing and how he chooses to invest, and how he operates on a board.
#smallrooms Podcast: Nudge Rewards' Jordan Ekers on mobile in the enterprise
Rob Kenedi sits down with Jordan Ekers, chief customer officer at Nudge Rewards, a mobile platform that allows retailers to communicate with front-line employees to enhance performance. Ekers discusses how mobile has permeated society and how they capitalize on it, how he compares running a startup to a more traditional business, when to take venture capital, and how to pick which market to focus on and how to say no.
#smallrooms Podcast: Collage's Elijah Moore on reinventing benefits in Canada
Rob Kenedi has a coffee with Elijah Moore, co-founder of Collage, a platform that helps businesses manage their HR and benefits in Canada. Moore talks about his past creating an unsuccessful startup, and how it affects the way he approaches his current company. He also touches on how he thinks about attacking an entrenched market with a variety of incumbents and new entrants, and the rationale behind taking a strategic investment from Diagram.
#smallrooms Podcast: Michael Kousaie of the TSX on going public early as a funding source
Rob 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 public and how the TSX helps companies get there, but also on the venture exchange as an alternate path to raising capital around the series A and B timeframe.
#smallrooms Podcast: Nudge co-founder Steven Woods on repeat entrepreneurship
Rob Kenedi sits down with Steven Woods, co-founder of Nudge, an AI platform that keeps salespeople on top of their networks and helps them close deals. Woods, formerly a co-founder of Eloqua – which went public and sold to Oracle – describes his approach to his second startup. He describes the path Eloqua took to become successful, his perspective on the acquisition process, and how to manage others’ perspectives on what an entrepreneur should do with their startup.
#smallrooms Podcast: Nudge co-founder Steven Woods on repeat entrepreneurship
Rob Kenedi sits down with Steven Woods, co-founder of Nudge, a platform that allows enterprises to manage workforce communications and drive employee advocacy. Woods describes doing customer validation of a problem before building a startup, then using a subsequent accelerator to grow their sales.
#smallrooms Podcast: Matthew Liebowitz of Plaza Ventures on growth investing
Rob Kenedi has a coffee with Matthew Liebowitz, partner at Plaza Ventures. Liebowitz talks about their approach to growth investing in Series A enterprise-focused SaaS startups and the fact that the fund is always raising capital rather than in huge lump sums. He also talks about the partner side of working at Plaza: what failure looks like when investing in this later phase of a startup’s development, and how partners are compensated only on performance of the portfolio.
#smallrooms Podcast: Ivan Tsarynny of PostBeyond on bootstrapping an enterprise startup
Rob Kenedi talks to Ivan Tsarynny, founder of PostBeyond, a platform that allows enterprises to manage workforce communications and drive employee advocacy. Tsarynny describes actually doing customer validation of a problem before building a startup, then using a subsequent accelerator to grow their sales.
#smallrooms Podcast: Sam Molyneux of Meta on AI, machine learning and science
In this special retrospective recorded one 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.
#smallrooms Podcast: Hany Fahim of VM Farms on DevOps as a Service
Rob 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.
#smallrooms Podcast: Nima Gardideh of Suto on bots and YC Fellowships
Host 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.
#smallrooms Podcast: Richard Tuck of Riipen
Rob has a chat with Richard of Riipen, a matchmaking system for companies and students that uses experiential learning. The company was recently featured in BetaKit, but Rob had a chance to get behind the scenes with another cofounder. Richard talks about the unorthodox start to Riipen, transforming from a school project that he was advising to a fully fledged social impact-focused business.
#smallrooms Podcast: Hussein Fazal of Snaptravel on bots & travel
Rob Kenedi sits down with Hussein Fazal, founder of SnapTravel, an SMS, Slack, and Facebook Messenger bot-based hotel booking service. Fazal 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 solving for the imperfect science of natural language processing and machine learning.
#smallrooms Podcast: Martin Kratky-Katz of Blockthrough on circumventing ad blocking
Rob Kenedi has a coffee with Martin Kratky-Katz, founder of Blockthrough, a technology that allows advertisers to circumvent ad blockers. Martin talks about the best way go to market with tools such as this, how he determined whether there was a market opportunity, and what he has learned from his false starts in the past.
#smallrooms Podcast: Balaji Gopalan of MedStack on enabling healthcare apps
Rob Kenedi sits down with Balaji Gopalan, founder of MedStack, a cloud-based platform that allows developers to easily create healthcare apps. Balaji discusses his experience building developer platforms for other firms such as Nymi and Desire2Learn, and then applying that skill to his own endeavour. Balaji also points out considerations in building healthcare software, including how they brought MedStack to market given the obvious constraints.
#smallrooms Podcast: Collision 2016 - Behind the Conference
Rob Kenedi travels to Collision 2016 in New Orleans to talk to startups – new and seasoned – as well as investors to answer the question: why travel to a conference and how do you hack it to get the most out of it? We talk to a handful of companies and investors to find out their tips and tricks to get what they need out of the conference. We talk to Jevelo, Shouty, My Lab Box, Cinderly, Love Guru, and Paired Media, as well as Trimantium Capital from Australia, and Boomtown from Colorado.
#smallrooms Podcast: Gary Saarenvirta of Daisy Intelligence
Rob 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.
#smallrooms Podcast: Michelle McBane of MaRS IAF on early stage investing
Rob Kenedi has a coffee with Michelle McBane, director at the MaRS Investment Accelerator Fund (IAF). Michelle explains the unique value proposition of the IAF in the Canadian investment ecosystem, their broad reach and success, and how their structure is very different than other investors, including the inability to participate in follow-on rounds.
#smallrooms Podcast: Kevin Kliman of Humi on experienced entrepreneurship
Rob 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.
#smallrooms Podcast: Mark Bailey of JobHubble
Rob Kenedi talks to Mark Bailey of JobHubble, a recruitment platform that uses influencers to find candidates. Mark discusses how and why he iterated on his platform based on market feedback, why to move their business into an incubator – in this case, the Ryerson DMZ, and how to truly know when you’re on the right path with your startup. In the revisited series of #smallrooms, Rob reconnects with the startup to see what’s happened since the last episode (typically a year later).
#smallroooms Podcast: Nick Chepesiuk of OnCall Health on building a telemedicine startup
Rob Kenedi chats with Nicholas Chepesiuk of OnCall Health, a freshly launched telemedicine startup. Nick details the challenge of launching a healthcare-focused startup in a heavily regulated environment, discovering the limitations of videoconferencing in patient treatment, and how he views his competition.
#smallroooms Podcast: Mark Bachman of FlipGive on sport tech and growth
Rob Kenedi talks with Mark Bachman of FlipGive, a fundraising-by-shopping platform for sports teams. Mark describes the shift from a services to a product company, how to avoid customizing a product for your loudest users, and what came out of going through the 500 Startups Distro Dojo, a growth-focused accelerator.
#smallrooms Podcast: Startupfest Part 2: Zoom.AI, Tunestars, Ubios, Tylio
On a second of two-part special summer-binge-listen version of Entrepreneurs in Small Rooms Drinking Coffee, the #smallrooms team recorded live at Startupfest 2016 in Montreal. This group of startups was recorded on the second day of StartupFest; tune in to listen to startups fresh off of pitching to investors and audience members. Rob chats with Zoom.AI, Tunestars, Ubios, Tylio.
#smallrooms Podcast: StartupFest Part 1: HelloMD, Parlay, Fans Unite, Gatsby
On a special summer-binge-listen version of Entrepreneurs in Small Rooms Drinking Coffee, the #smallrooms team recorded episodes live at StartupFest 2016 in Montreal. This group of startups were recorded on the first day of StartupFest; tune in to listen startups fresh off of pitching to investors and audience members. Rob chats with HelloMD, Parlay, Fans Unite, and Gatsby.
#smallrooms Podcast: Daniel Klass of Klass Capital
Rob 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.
#smallrooms Podcast: Andrew Graham of Borrowell
Rob 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.
#smallrooms Podcast: Sam Ifergan of iGan Partners
Rob 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.
#smallrooms podcast: Brice Scheschuk of Globalive Capital & Wind Mobile on investing
Rob 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.
#smallrooms Podcast: Jane Podbelskaya of Georgian Partners
Rob 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.
#smallrooms podcast: Chris Bryson of Unata on success in retail
Rob 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.
#smallrooms podcast: Andrew Peek on Shopify acquisitions and too much funding
Rob 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.
#smallrooms podcast: Adam Epstein of Tab on being acquired
Rob 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. In the revisited series of #smallrooms, Rob reconnects with the startup to see what’s happened since the last episode (typically a year later).
Michael Katchen of Wealthsimple on scale & trust
Rob Kenedi sits down again 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).
#smallrooms podcast: Michael Van of Four Walls on not raising and Startup Next
Rob 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 a pre-accelerator, Techstars’ Startup Next, on 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.
#smallrooms podcast: Adam Rabie of Big Terminal
Rob 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.
#smallrooms podcast: Roger Chabra of Rho Ventures
Rob Kenedi has a coffee with Roger Chabra, partner at Rho Canada Ventures. Roger is 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.
#smallrooms podcast: Vitaly Pecherskiy of StackAdapt on branded content
Rob Kenedi speaks with Vitaly Pecherskiy of StackAdapt, a branded content native advertising platform. Fresh off a Series A, Vitaly explains how the team bootstrapped its 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.
#smallrooms podcast: Michael Kovacs of OpenChannel
Rob Kenedi has a coffee with Michael Kovacs, cofounder OpenChannel, a startup that allows technology companies to instantly create app stores to grow their offering. A relatively early-stage startup that’s in revenue, Michael reflects on bootstrapping a B2B business, choosing to go to an accelerator, Alchemist, and the right time to take venture funding.
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