Entrepreneurs in Small Rooms Drinking Coffee

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

CrowdRiff by #smallrooms

Trainer+ by #smallrooms

Matt Roberts | ScaleUP Ventures by #smallrooms

Nudge Rewards Revisited by #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.

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 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 respect to the behaviour of startups in Silicon Valley and their reluctance to go public.

Nudge.ai by #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 failure looks like when investing into this later phase of a startup's development.

PostBeyond by #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 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 about iterating on their product, and how to build an exceptionally complex product that is net new to an industry.

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.

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. 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 took it through the Y Combinator Fellowship program.

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. They also discuss the 10 incubators / accelerators Riipen went through, losing your tech team, and what it is like running a startup that’s distributed in nature. Disclosure: Richard is a client of TWG’s where Rob serves as Entrepreneur in Residence.

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 user experience as well as the how to solve for the imperfect science of natural language processing and machine learning.

Blockthrough by #smallrooms

Medstack by #smallrooms

Collision 2016 Investors by #smallrooms

Collision 2016 Entrepreneurs by #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 companies such as IBM.

Michelle McBane | IAF by #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, 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.

JobHubble Revisited by #smallrooms

OnCall Health by #smallrooms

Flipgive by #smallrooms

Tylio by #smallrooms

Ubios by #smallrooms

Tunestars by #smallrooms

ZoomAI 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 Aaron Jun of Gatsby, a event planning solution for groups. Aaron focuses on messaging as a user interface and getting out of beta.

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 engagement and retention problem.

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 business when one cannot use traditional advertising to acquire customers.

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.

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.

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 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.

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. Brice also details a unique perspective on Canadian startups and details an articulate counter-narrative to what success looks like for a Canadian startup.

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. Disclosure: Freshbooks and Shopify are clients of TWG, where Rob serves as Entrepreneur in Residence.

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.

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. 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.

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 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 client of TWG, where Rob serves as Entrepreneur in Residence.

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 sized businesses made more sense, and their decision not to raise capital at all.

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.

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 #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 the scenes, and how that has affected her investment thesis.

Rubikloud by #smallrooms

Trulioo by #smallrooms

PopRx by #smallrooms

Venzee by #smallrooms

Flixel by #smallrooms

Wave by #smallrooms

From the archives!

Tiny Hearts by #smallrooms

BlancRide by #smallrooms

Zeitdice by #smallrooms

Mediazoic by #smallrooms

Instaradio / Raur Revisited by #smallrooms

MakerBloks by #smallrooms

Sampler Revisited by #smallrooms

Tunestars by #smallrooms

Hykso by #smallrooms

Turnstyle Revisited by #smallrooms

We sit down with Carl of Nymi, creators of the Nimy Band

Contract Cloud by #smallrooms

Dealflicks by #smallrooms

Kiddom by #smallrooms

Our first episode in an echoey room with Kevin Kliman, founder of Raur / Instaradio.

We reconnect with Zak 10 months later to see how far Upverter has come. Check out Episode 5 for part 1!

Rob sits down with Sam, cofounder of Sciencescape, a startup that helps academics stay on top of their fields by delivering research to them in real time in an intelligent manner.

Rob follows up with Jason of Forewards now that the startup has effectively closed down. Check out Episode 7 for part 1!

IdeaBoost Graduation by #smallrooms

Rob chats with Jeremy, founder of Sensassure, a wearables startup that helps manage incontinence for the elderly.

Rob speaks with Alex, founder of MyBestHelper, a startup that helps families connect with people who can help them accomplish tasks such as babysitting, school pickups, and more.

Rob sits down with Vikram Somasundaram, founder of Edusight, an education platform for teachers.

Rob talks to Michael Back, founder of HonkMobile, an app that lets you pay for parking with your phone.

Rob chats with Aran Hamilton, founder of Vantage Analytics, an insight and action platform for retailers.

Rob talks to Jeremy Bell, founder of Wattage, which allows you to build and ship hardware via the web.

Rob chats with Mark Goh, founder of ChargeSpot, a wireless charging startup.

Rob sits down with Adam Epstein, founder of Tab, a platform that provides mobile payments for dining.

Rob has a conversation with Ryan Porter, founder of Raise Your Flag, a career path platform for those without a college or university degree.

Rob talks to Alkarim Nasser, founder of Gallop, a prescriptive mobile marketing plaform.

Rob chats with Natasha Baker, founder of SnapEDA, a electronic design community centered around a free, collaborative CAD library.

Rob kicks off the new season with Katherine Hague, founder of The Blueprint / Shoplocket, which is now a discovery platform for the next wave of consumer electronics.

Rob talks to Chris Gilpin, founder of Turnstyle, a customer engagement platform for retailers.

Rob chats with Shannon Fox, founder of Canopy, a community curated Amazon storefront.

Rob talks with to Mark Bailey, founder of Job Hubble, which rewards people for job referrals.

Rob chats with Chris Bryson, founder of Unata, a retail marketing platform.

Rob interviews Matthew Slutsky, founder of BuzzBuzzHome, a website which improves the way people find new construction homes.

Rob speaks to Dessy Daskalov, founder of Nudge Rewards, a platform that uses smartphones to increase employee engagement.

Rob talks to Michael Budd, founder of Organics Live, a local, sustainable organics delivery franchisor.

My chat with Olivier Berger, founder of Wondereur, the art platform that grants access to intimate photojournalistic stories behind the work of worldwide artists, and you can buy the art itself.

Rob speaks with Marie Chevrier, founder of Sampler, the social platform that allows marketers to revolutionize how they target consumers with samples.

Rob speaks with Donny Ouyang, founder of Rayku, the online math tutoring platform that connects students to expert tutors.

Rob talks to Zak Homuth, founder of Upverter, a collaborative hardware engineering platform.

Rob speaks with Jason Dea, founder of Forewards, a referral platform for Shopify sellers.

Rob chats with Jacob Sheehy, founder of PressureNet, which uses smartphones to predict weather.