Meeting with mentors and investors

Published On Jul 6, 2022

Startupfest 2022 is all about meaningful connections and serendipitous interactions. That means less on-stage content, and more networking opportunities with fresh faces. And while Startupfest is always packed with smart attendees, fellow founders, and seasoned investors, this year we’re stacking the deck. 

We reached out to dozens of experts—including past speakers who are serial entrepreneurs themselves—asking them to play the role of mentor this year. They’ll be on stage for some interactive sessions, and roaming the venue meeting with startups.

These aren’t the proverbial “armchair quarterbacks.” Many of them have walked in your shoes, building and exiting startups themselves. They’re here to give back, whether that’s support, advice, and maybe even an investment—if that’s where conversations lead.


There’s no such thing as a bad question, but there is such a thing as a great question.

After two years of being glued to our screens, we all could use a little help getting back into the swing of things, meeting new people face-to-face, and putting our best foot forward when networking. To get you ready for what might just be a pivotal meeting in your startup history, we asked our mentors, “what are the smartest questions a startup could ask you?” Here’s what they said:


Tap into their expertise and experience

Mentors and investors at Startupfest have many years of experience with valuable knowledge to tap into. Doing a bit of research before the event and understanding who you’re talking to can take a conversation from a simple, shallow hello to a strategic step forward for your business. 

  • Check out who’s coming by reading bios from our website and viewing their experiences on LinkedIn.
  • Speak with mentors or investors that fit your company’s niche or market, and ask targeted questions.
  • Ask questions that use examples from their portfolio or past experiences.


Ask for advice on specific challenges or goals

The best questions are tailored to a particular goal you’ve set or challenge you’re facing. That may depend on the stage your startup is at, your vertical, or your business model. Asking specific questions around what your company faces today will allow you to leave Startupfest with practical knowledge you can use right away. Some examples might include:

  • Scaling into emerging or developing markets – What does my Canadian company need to scale into a developing market?
  • Questions about fundraising – What is the best type of funding to help me achieve my startup growth ambitions?
  • Finding and keeping clients or customers – I’m losing clients, how can I reduce customer churn?
  • Building company culture – What are the best practices to manage a remote workforce and build the company culture?


Discuss best practices to scale your business

When meeting with potential investors, they want to know if your company can scale over time. Using your time at Startupfest to understand best practices when scaling or how to prepare for it in the future can help you secure funding in the long-run. Some of the questions mentors suggested include:

  • You are still in the early stages and want to scale eventually – How do you build for scale from the start?
  • Building trust in your company to scale – How do we build good, enduring habits as a company to scale fast and build trust with our customers?
  • Identifying growth goals and working backwards – How do I work backwards from my intended outcome to make informed decisions for growth?


Understand how they can support you

Working with mentors and investors is an important aspect of running a successful startup. Knowing how they can support you as a founder and help you reach your goals as a company is vital for a healthy, business relationship. And it doesn’t hurt to have a concrete ask:

  • When things don’t go as planned – How do you support founders when things go wrong?
  • Developing your story and pitch – Would you be open to working on my pitch together?
  • Reaching your goals – Why should I take your investment? How can you help me reach my objectives?


Lessons learned

Startups are roller coasters, and our mentors and investors have gone through the ups and downs. Many have found success even after failure. Their expertise and lived experiences are a valuable resource which can provide insight on how to avoid making common mistakes and making more informed decisions. Learn from their background with questions like:

  • Ask what they’ve seen from other founders – What are some common mistakes you see founders make?
  • Use their expertise to better understand your field – What have been the most effective business model decisions in my field? 
  • Taking advice from others – How do I know whose advice to listen to or who would make a good advisor?

The mentors this year are another example of how Startupfest is focusing on things that help real founders grow their businesses. They’re traveling from afar to help the next generation of entrepreneurs survive and thrive, so make the most of this unprecedented access to some of the smartest startup minds in the world.

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