Rob talks startups and finance with Michael Katchen, founder of Wealthsimple, a technology platform that manages your investments. Originally published in June, 2015.By #smallrooms

CrowdRiff by #smallroomsBy #smallrooms

Trainer+ by #smallroomsBy #smallrooms

Matt Roberts | ScaleUP Ventures by #smallroomsBy #smallrooms

Nudge Rewards Revisited by #smallroomsBy #smallrooms

Moore talks about how his past creating an unsuccessful startup and how it affects the way he approaches his current company, 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.By #smallrooms

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 pubilc and how the TSX helps companies get there, but also focuses on the venture exchange as an alternate path to raising capital arou…

Nudge.ai by #smallroomsBy #smallrooms

Rob 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 fail…

PostBeyond by #smallroomsBy #smallrooms

In 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 j…

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 f…

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 ho…

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 f…

Rob 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…

Blockthrough by #smallroomsBy #smallrooms

Medstack by #smallroomsBy #smallrooms

Collision 2016 Investors by #smallroomsBy #smallrooms

Collision 2016 Entrepreneurs by #smallroomsBy #smallrooms

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 compa…

Michelle McBane | IAF by #smallroomsBy #smallrooms

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. Kevin describes what he learned from his last startup, Instaradio / Raur, and how he approached creating his next startup, taki…

JobHubble Revisited by #smallroomsBy #smallrooms

OnCall Health by #smallroomsBy #smallrooms

Flipgive by #smallroomsBy #smallrooms

Tylio by #smallroomsBy #smallrooms

Ubios by #smallroomsBy #smallrooms

Tunestars by #smallroomsBy #smallrooms

ZoomAI by #smallroomsBy #smallrooms

On 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.By #smallrooms

On 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 enga…

On 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.…

On 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 busines…

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 …

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.By #smallrooms

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. Sam details iGan's focus on early stage companies and how he belie…

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 indi…

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, pattern…

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 f…

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 differ…

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.…

Rob 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 revisi…

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 an pre-accelerator, Techstars Startup Next, starting down a consumer path to get to market but why going after small and medium siz…

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 fres…

Rob 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.…

Rob 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.…

OpenChannel by #smallroomsBy #smallrooms

In 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 th…

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