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Entrepreneurs in Small Rooms Drinking Coffee

Entrepreneurs in Small Rooms Drinking Coffee

By smallrooms

Entrepreneurs in Small Rooms Drinking Coffee, or #smallrooms, is a live, unfiltered podcast where Rob Kenedi talks candidly with entrepreneurs and investors about the details of starting a tech company. Get into the trenches with founders going through the process of building a technology company in real time.
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WealthSimple

Entrepreneurs in Small Rooms Drinking CoffeeDec 01, 2017

00:00
37:14
WealthSimple

WealthSimple

Rob talks startups and finance with Michael Katchen, founder of Wealthsimple, a technology platform that manages your investments. Originally published in June, 2015.
Dec 01, 201737:14
CrowdRiff

CrowdRiff

CrowdRiff by #smallrooms
May 30, 201741:58
Trainer+

Trainer+

Trainer+ by #smallrooms
Apr 21, 201747:56
Matt Roberts | ScaleUP Ventures

Matt Roberts | ScaleUP Ventures

Matt Roberts | ScaleUP Ventures by #smallrooms
Apr 14, 201744:41
Nudge Rewards Revisited

Nudge Rewards Revisited

Nudge Rewards Revisited by #smallrooms
Mar 31, 201739:03
Collage

Collage

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.
Mar 17, 201744:05
Michael Kousaie - TSX

Michael Kousaie - TSX

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.
Mar 10, 201743:28
Nudge.ai

Nudge.ai

Nudge.ai by #smallrooms
Feb 23, 201738:08
Matt Leibowitz | Plaza Ventures

Matt Leibowitz | Plaza Ventures

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.
Feb 10, 201748:37
PostBeyond

PostBeyond

PostBeyond by #smallrooms
Feb 02, 201743:34
Meta | Acquired by Chan Zuckerberg Initiative

Meta | Acquired by Chan Zuckerberg Initiative

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.
Jan 28, 201736:50
VM Farms

VM Farms

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.
Jan 13, 201735:28
Suto

Suto

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.
Jan 06, 201736:08
Riipen

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. 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.
Dec 30, 201637:39
SnapTravel

SnapTravel

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.
Dec 22, 201644:20
Blockthrough

Blockthrough

Blockthrough by #smallrooms
Oct 28, 201638:22
Medstack

Medstack

Medstack by #smallrooms
Oct 17, 201633:49
Collision 2016 Investors

Collision 2016 Investors

Collision 2016 Investors by #smallrooms
Oct 06, 201620:13
Collision 2016 Entrepreneurs

Collision 2016 Entrepreneurs

Collision 2016 Entrepreneurs by #smallrooms
Sep 29, 201611:17
Daisy Intelligence

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.
Sep 15, 201635:42
Michelle McBane | IAF

Michelle McBane | IAF

Michelle McBane | IAF by #smallrooms
Sep 09, 201648:03
Humi

Humi

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.
Sep 02, 201644:54
JobHubble Revisited

JobHubble Revisited

JobHubble Revisited by #smallrooms
Aug 26, 201640:48
OnCall Health

OnCall Health

OnCall Health by #smallrooms
Aug 11, 201636:07
Flipgive

Flipgive

Flipgive by #smallrooms
Aug 02, 201643:07
Tylio

Tylio

Tylio by #smallrooms
Jul 30, 201631:53
Ubios

Ubios

Ubios by #smallrooms
Jul 30, 201638:25
Tunestars

Tunestars

Tunestars by #smallrooms
Jul 30, 201632:00
ZoomAI

ZoomAI

ZoomAI by #smallrooms
Jul 30, 201632:06
Gatsby

Gatsby

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.
Jul 23, 201632:48
Fans Unite

Fans Unite

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.
Jul 23, 201632:30
Parlay

Parlay

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.
Jul 23, 201631:21
HelloMD

HelloMD

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.
Jul 23, 201635:03
Daniel Klass | Klass Capital

Daniel Klass | 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.
Jun 30, 201648:37
Borrowell

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.
Jun 23, 201645:37
Sam Ifergan | iGan Partners

Sam Ifergan | 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. 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.
Jun 16, 201654:37
Brice Scheschuk | Globalive Capital

Brice Scheschuk | Globalive Capital

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.
Jun 09, 201657:16
Jane Podbelskaya | Georgian Partners

Jane Podbelskaya | 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. Disclosure: Freshbooks and Shopify are clients of TWG, where Rob serves as Entrepreneur in Residence.
Jun 02, 201645:38
Unata Revisited

Unata Revisited

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.
May 21, 201642:49
Andrew Peek

Andrew Peek

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.
May 06, 201648:00
Tab Revisited

Tab Revisited

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.
Apr 21, 201649:02
Wealthsimple Revisited

Wealthsimple Revisited

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.
Apr 14, 201644:51
Four Walls

Four Walls

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.
Apr 08, 201638:24
Big Terminal

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.
Mar 18, 201642:02
Roger Chabra | Rho Ventures

Roger Chabra | Rho Ventures

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.
Mar 10, 201654:24
StackAdapt

StackAdapt

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.
Feb 04, 201637:20
OpenChannel

OpenChannel

OpenChannel by #smallrooms
Jan 28, 201637:20
Nicole Verkindt

Nicole Verkindt

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.
Jan 22, 201638:26
Rubikloud

Rubikloud

Rubikloud by #smallrooms
Dec 31, 201537:20
Trulioo

Trulioo

Trulioo by #smallrooms
Dec 17, 201532:45
PopRx

PopRx

PopRx by #smallrooms
Nov 24, 201540:02
Venzee

Venzee

Venzee by #smallrooms
Nov 19, 201523:26
Flixel

Flixel

Flixel by #smallrooms
Nov 12, 201539:26
Wave

Wave

Wave by #smallrooms
Nov 05, 201539:54
EventMobi

EventMobi

From the archives!
Oct 30, 201533:20
Tiny Hearts

Tiny Hearts

Tiny Hearts by #smallrooms
Oct 22, 201537:20
BlancRide

BlancRide

BlancRide by #smallrooms
Oct 15, 201534:51
Zeitdice

Zeitdice

Zeitdice by #smallrooms
Sep 24, 201537:20
Mediazoic

Mediazoic

Mediazoic by #smallrooms
Sep 17, 201537:20
Instaradio / Raur Revisited

Instaradio / Raur Revisited

Instaradio / Raur Revisited by #smallrooms
Sep 03, 201535:37
MakerBloks

MakerBloks

MakerBloks by #smallrooms
Aug 27, 201527:42
Sampler Revisited

Sampler Revisited

Sampler Revisited by #smallrooms
Aug 20, 201535:52
Tunestars

Tunestars

Tunestars by #smallrooms
Aug 13, 201519:40
Hykso

Hykso

Hykso by #smallrooms
Aug 06, 201527:24
Turnstyle Revisited

Turnstyle Revisited

Turnstyle Revisited by #smallrooms
Jul 30, 201537:20
Nymi

Nymi

We sit down with Carl of Nymi, creators of the Nimy Band
Jul 27, 201539:04
Contract Cloud

Contract Cloud

Contract Cloud by #smallrooms
Jul 15, 201539:27
Dealflicks

Dealflicks

Dealflicks by #smallrooms
Jul 15, 201540:02
Kiddom

Kiddom

Kiddom by #smallrooms
Jul 15, 201534:57
Instaradio / Raur

Instaradio / Raur

Our first episode in an echoey room with Kevin Kliman, founder of Raur / Instaradio.
Jul 03, 201557:40
Upverter Revisited

Upverter Revisited

We reconnect with Zak 10 months later to see how far Upverter has come. Check out Episode 5 for part 1!
Jul 02, 201539:21
Meta (formerly Sciencescape)

Meta (formerly Sciencescape)

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.
Jun 30, 201536:04
Forewards Revisited

Forewards Revisited

Rob follows up with Jason of Forewards now that the startup has effectively closed down. Check out Episode 7 for part 1!
Jun 25, 201532:09
IdeaBoost Graduation

IdeaBoost Graduation

IdeaBoost Graduation by #smallrooms
Jun 25, 201511:55
Sensassure

Sensassure

Rob chats with Jeremy, founder of Sensassure, a wearables startup that helps manage incontinence for the elderly.
Jun 25, 201531:09
MyBestHelper

MyBestHelper

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.
Jun 25, 201533:25
Edusight

Edusight

Rob sits down with Vikram Somasundaram, founder of Edusight, an education platform for teachers.
Jun 25, 201533:09
Honk Mobile

Honk Mobile

Rob talks to Michael Back, founder of HonkMobile, an app that lets you pay for parking with your phone.
Jun 25, 201537:26
Vantage Analytics

Vantage Analytics

Rob chats with Aran Hamilton, founder of Vantage Analytics, an insight and action platform for retailers.
Jun 25, 201537:26
Wattage

Wattage

Rob talks to Jeremy Bell, founder of Wattage, which allows you to build and ship hardware via the web.
Jun 25, 201546:07
ChargeSpot

ChargeSpot

Rob chats with Mark Goh, founder of ChargeSpot, a wireless charging startup.
Jun 25, 201534:09
Tab

Tab

Rob sits down with Adam Epstein, founder of Tab, a platform that provides mobile payments for dining.
Jun 25, 201536:08
Raise Your Flag

Raise Your Flag

Rob has a conversation with Ryan Porter, founder of Raise Your Flag, a career path platform for those without a college or university degree.
Jun 25, 201534:44
Gallop

Gallop

Rob talks to Alkarim Nasser, founder of Gallop, a prescriptive mobile marketing plaform.
Jun 25, 201530:42
SnapEDA

SnapEDA

Rob chats with Natasha Baker, founder of SnapEDA, a electronic design community centered around a free, collaborative CAD library.
Jun 25, 201536:58
ShopLocket

ShopLocket

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.
Jun 25, 201538:50
Turnstyle

Turnstyle

Rob talks to Chris Gilpin, founder of Turnstyle, a customer engagement platform for retailers.
Jun 25, 201536:08
Canopy

Canopy

Rob chats with Shannon Fox, founder of Canopy, a community curated Amazon storefront.
Jun 25, 201536:08
JobHubble

JobHubble

Rob talks with to Mark Bailey, founder of Job Hubble, which rewards people for job referrals.
Jun 25, 201536:08
Unata

Unata

Rob chats with Chris Bryson, founder of Unata, a retail marketing platform.
Jun 25, 201537:24
BuzzBuzzHome

BuzzBuzzHome

Rob interviews Matthew Slutsky, founder of BuzzBuzzHome, a website which improves the way people find new construction homes.
Jun 25, 201537:17
Nudge Rewards

Nudge Rewards

Rob speaks to Dessy Daskalov, founder of Nudge Rewards, a platform that uses smartphones to increase employee engagement.
Jun 25, 201535:56
Organics Live

Organics Live

Rob talks to Michael Budd, founder of Organics Live, a local, sustainable organics delivery franchisor.
Jun 25, 201534:50
Wondereur

Wondereur

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.
Sep 29, 201435:31
Sampler

Sampler

Rob speaks with Marie Chevrier, founder of Sampler, the social platform that allows marketers to revolutionize how they target consumers with samples.
Sep 29, 201433:31
Rayku

Rayku

Rob speaks with Donny Ouyang, founder of Rayku, the online math tutoring platform that connects students to expert tutors.
Sep 29, 201436:32
Upverter

Upverter

Rob talks to Zak Homuth, founder of Upverter, a collaborative hardware engineering platform.
Sep 29, 201437:30
Forewards

Forewards

Rob speaks with Jason Dea, founder of Forewards, a referral platform for Shopify sellers.
Sep 29, 201432:16
PressureNet

PressureNet

Rob chats with Jacob Sheehy, founder of PressureNet, which uses smartphones to predict weather.
Sep 29, 201435:37