Joining FreshBooks

When I entered the startup World in the late 90s I set a goal for myself to become a VC in ten years. It took me eleven, but in late 2010 I achieved that goal joining Real Ventures.

I’ve had a great run at Real. We have been Canada’s most active seed venture fund with almost forty venture investments.  We have invested in some great teams and already have breakout hyper-growth companies including Frank & Oak and Cinemagram. Finally, we have already had four positive exits. All good.

But as I looked back and reflected on things over the end of year holidays, I found myself missing operating inside companies. I’ve been fortunate and privileged to be part of the Real team and to work with so many great entrepreneurs. But it was time for me to hunker down and focus on just one company as a full time team member.

So, I am pleased to announce that I am joining FreshBooks, a company that needs no introduction, especially to the Canadian startup community. I have been close to this company for a number of years and have watched it grow. It is a truly special company. And even though it’s been around for a while, it’s just getting started.

I will be leading business & corporate development at FreshBooks, helping build a portfolio of relationships that will propel our growth.

I will continue to be involved as a Venture Partner at Real. I’d like to take this opportunity to thank my partners Alan, JS and John, and the team members for a great 2+ years as a VC. Real has done some great things. And, like FreshBooks, it too is just getting started.

  • friv 2 friv 3 friv 4

    Congratulations, Mark! Another step for your grand goals and hope you still have time DJ

  • yepi250

    Great article! I am loving it!! Will be back later to read some more.

  • kizi 2

    Great post,thanks,this is going to help me a lot.

  • Friv 4

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  • Pingback: FreshBooks wins iPhone award, hires VC investor | IT Business()

  • Sean Sherwood

    They’re lucky to have you Mark, congrats!

    • Mark MacLeod

      Thanks Sean!

  • Nariman Selimkhanov

    My belated congrats, Mark, and welcome back to Toronto! Lucky Freshbooks!..

    • Mark MacLeod

      Thanks Nariman.

  • Fang Yang

    Congratulations, Mark! Another step for your grand goals and hope you still have time on your DJ music :)

    • Mark MacLeod

      Thanks Fang. Will definitely keep pumping out the music

  • VinceSurette

    Mark, sorry to see you go (luv ya man). I agree, there’s nothing like the buzz (or shivers) of ops. Will miss your level head. Best of the best to you.

    • Mark MacLeod

      Thanks Vince. Keep rocking it with Wajam and others. And keep in touch

  • davduf

    Woah! Huge news. Congrats Freshbooks on getting a world class A-Player. Congrats Mark on joining a superb company.
    Now, last time you went from operations to VC, I did the exact opposite. Am I supposed to switch again? (I’m not moving to TO, though).

    • Mark MacLeod

      Thanks a lot David. You stay just where you are :)

  • Adam Perkins

    Congrats Mark! :)

  • Sanjeev Arora

    Congratulations Mark, Freshbooks is blessed..! Great to have you in Toronto.

    • Mark MacLeod

      Thank you Sanjeev. I’m the lucky one

  • Joe Rideout

    Congrats Mark! Toronto welcomes you :)

    • Mark MacLeod

      Thanks Joe

  • Pingback: FreshBooks wins iPhone award, hires VC investor | My Blog()

  • Abdallah Al-Hakim

    Congrats Mark. You were one of the few Canadian VCs whom I enjoyed following for their valuable input regarding businesses and the general entrepreneurial ecosystem. I am sure you will continue provide such input through the different social media channels!

    • Mark MacLeod

      Thanks Abdallah. Most of my time blogging has been on the company side, vs. VC. Will keep on going.

  • Paul Sullivan

    Congrats Mark! It’ll be great to hear your perspective from “the other side of the table”. Oh wait, that’s already taken. No matter – all the best in the new role!

    • Mark MacLeod

      Thanks Paul

  • Lisa Coleman-Delorme

    Hey Mark, Stop in at Rent frock Repeat when you get a chance – we are your new neighbours and would love to personally welcome you to the building!

    • Mark MacLeod

      Hey neighbour. Nice to meet you

  • Daniel Haran

    Wow, what a surprise! Congrats & see you in TO sometime :)

    • Mark MacLeod

      You live in TO?

      • Daniel Haran

        I’m in Kathmandu right now; leaving for Bangkok on Friday. I should be back in North America by May, earlier if my latest idea takes off :)

  • Lally Rementilla

    Congratulations, Mark. Sounds like a win-win. See you around town.

    • Mark MacLeod

      Thanks Lally. Absolutely. See you around

  • Marc Lennox

    Congrats Mark, all the best to you and your family with the new adventure.

    • Mark MacLeod

      Thx Marc

  • Jacou

    Wow, congrats and good luck in this new adventure.

    • Mark MacLeod

      Thx Jacou. Should be fun

  • Tony Lam

    Congrats Mark. The venture community’s loss is Freshbooks’ gain. Best wishes.

    • Mark MacLeod

      Thx Tony. See you Tuesday

  • jenniferlum

    Congrats Mark!

    • Mark MacLeod

      Thx Jennifer. See you in TO sometime?

  • garydpdx

    Best of luck to you, Mark! :)

  • Roger Wilson

    Congrats Mark and welcome to Toronto!

  • philgo20

    Congrats for the move Mark. On could think you’re leaving because of the crazy weather we’re having right now. See you in TO.

    • Mark MacLeod

      Anything to escape this cold…:)

  • leilaboujnane

    Operations pretty much beats everything else! :) Welcome back to the real side of building! Will be nice to have you in TO too. The weather is going to feel balmy. A bientot!

    • Mark MacLeod

      Thx Leila. Looking forward to being back operating and back in TO.

  • Mark Evans

    I hope you’ll continue to write the blog. Looking forward to get some inside insight.


    • Mark MacLeod

      Definitely will keep blogging. Won’t be sharing too many insider secrets though :)

  • Luc Vezina

    Congrats. I have a long list of feature requests that I’ll send your way :-)

    • Mark MacLeod

      Bring them on…

  • Michael Nus

    Congratulatons, Mark. I know you’ll do amazing things with Freshbooks. Go get em!

    • Mark MacLeod

      Thanks Michael. See you around town soon

  • Ken Seto

    Congrats Mark! It’ll be great to have you in Toronto :)

    • Mark MacLeod

      Absolutely. Much easier to meet over Manhattans…

  • Jonas

    Congratulations Mark (and Freshbook)! Exciting news for Toronto as well :)

    • Mark MacLeod

      Thanks Jonas. It’s been 17 years since I lived in TO. Will be fun to be back

  • Mark O’Sullivan

    Awesome news! Change is a very good thing. I can attest to that. Freshbooks is lucky to have you, and I know you will enjoy Toronto!

    • Mark MacLeod

      Thanks Mark. Hope you’re enjoying SFO

  • Alex Eberts

    Congrats Mark – I know you’ll be missed at Real and also in Montreal. Freshbooks is smart (and luck) to have you join them! very best wishes, Alex

    • Mark MacLeod

      Thanks Alex.

  • Jagath Narayan

    Congrats Mark. That is definitely an exciting move!!

    • Mark MacLeod

      Thanks Jagath

  • ptelio

    Montreal will miss you dearly Mark. Hope you will come back often. In July at the very least :-) All the best to you and Freshbooks.

    • Mark MacLeod

      Thanks Phil. I’ll definitely be back often

  • ddebow

    Amazing! You are going to be great… and make Freshbooks even greater. Exciting.

    • Mark MacLeod

      Thanks Dan. No pressure :)

  • Charles Brun

    Congrats Mark! Very happy for you! Sad to see you leave for Toronto though! :)

    • Mark MacLeod

      Thanks Charles. Really enjoyed my time in Montreal. Great community here and it;s only just beginning with Notman getting going

  • Casey McKinnon

    Looking forward to having you in the office full-time Mark… excited about learning a lot from you.

    • Mark MacLeod

      Thanks Casey. Looking forward to working with you

  • Rob Saric

    Best of luck Mark!

    • Mark MacLeod

      Thanks Rob

  • Benjamin Yoskovitz

    Mark – congrats on making a big leap. I’m sure it’ll be a hell of a ride.

    When do you move from Montreal?

    • Mark MacLeod

      Thanks Ben. End of March

  • Facebook User

    Congrats, Mark! FreshBooks is lucky to have you.

    • Mark MacLeod

      Thanks george

  • thomas

    Amazing news Mark. Congrats. Glad to hear you will still be keeping a hand in the venture community as well.

    • Mark MacLeod

      Thanks Thomas.

  • Divesh Sisodraker

    Congratulations Mark! All the best at Freshbooks!

    • Mark MacLeod

      Thanks Divesh

  • Paul Burger

    Huge congrats! All the best!

    • Mark MacLeod

      Thanks Paul

  • davidcrow

    Congrats @startupcfo:disqus amazing news for @mikemcderment and the @freshbooks team!

    Are you moving to Toronto?!!!!!

    • Mark MacLeod

      Thanks David. Yep, already bought a house

      • Mark Zohar

        What neighbourhood? Looking forward to seeing you around town.

        • Mark MacLeod

          Kingsway area

        • Bryan McCaw

          Welcome to my hood Mark. Come by for a glass of wine sometime and I’ll give you tips on the neighbourhood. 380 Prince Edward.

        • Mark MacLeod

          Wow, that’s close Bryan. We move end of March. Will let you know once we are all settled in.

      • jevon


  • Marc Gingras

    Coming back to the light from the dark side. Congrats.

    • Mark MacLeod


    • Evan Prodromou

      He’s like Anakin Skywalker.

  • derekjsmyth

    Congrats Mark! All the best to you a Freshbooks team.

    • Mark MacLeod

      Thanks Derek

  • Ivan Paramonau

    As they say in Russia – a gifted person is gifted in everything. Congrats!

    • Mark MacLeod

      I like that saying :)

  • Chrisarsenault

    Big Move. Awesome. Mike is a smart man bringing you in full time.

    • Mark MacLeod

      Thanks Chris.

  • Harley

    congrats MM. #hustle :)

    • Mark MacLeod

      You’ll have to show me your partnering hustle secrets :)

  • luc levesque

    Congrats Mark

    • Mark MacLeod

      Thanks Luc

  • Kevin Swan

    Wow – totally unexpected! Huge respect for following your passions though, Mark. All the best and look forward to continue working together.

    • Mark MacLeod

      Thanks a lot Kevin. Really looking forward to getting back to operating. Let’s stay in touch