Tips from a first-time entrepreneur: Questions to ask during a mentoring session…

TiEcon 2013: The world’s largest conference for entrepreneurs is almost here (May 17-18, 2013), and MentorCloud is proud to be strategic partner of TiE. My own entrepreneurial-gene got turned on when I attended TiEcon few years ago, and the e-journey has been fantastic ever since, leading up to MentorCloud.
At this year’s TiEcon, more than 250 mentoring sessions between aspiring entrepreneurs and mentors will happen live as part of TiE’s MentorConnect program, powered by MentorCloud. As a first-time entrepreneur and a direct beneficiary of mentorship from world-class mentors, I learned a few lessons which might be helpful for TiE mentees, as they prepare for their ‘priceless mentoring sessions‘ with TiE mentors at TiEcon 2013. Right questions will bring out the right wisdom from the Mentors so here are a few I suggest for your sessions:

  1. What are 3 things investors look for in a start-up before considering an investment?
  2. Having a Mentor is critical for every entrepreneur. What are 3 things Mentors like you look for in an entrepreneur to want to spend time with me and my team?
  3. Seed funding to prove your idea is hard to get these days. Everyone seems to want the hockey-stick growth point to invest in. What should aspiring entrepreneurs do in this situation? How can they get to that point without access to seed funding?
  4. What is your advice for those who have had great success in their professional careers but never been an entrepreneur? How should they jump into the world of entrepreneurship? How did you start your first venture?
  5. What in your opinion is an ideal-time to approach a VC for funding, especially in today’s environment?
  6. I am working full time and spend nights/weekends to build on my product idea. How and when should I switch to full time? Doing both is tough and frustrating.
  7. Do you think prior entrepreneurial success is a key factor for you and other VC’s to believe in?
  8. Investors rarely say ‘No’ to an entrepreneur and so lot of time gets wasted in following up. How can entrepreneurs quickly figure out if an investor is interested or not?
  9. What is the best way to sign-up Alpha and Beta Customers? How much should I push for some revenue from them, or should I just do them for free to prove my product’s value proposition?
  10. Some say patents are critical to build IP, while others strike it off as a waste of time and money. What is your opinion and should entrepreneurs spend time and money writing patents, or do you think a product with a traction is more important.
  11. Raising funding and building a team is a catch-22 situation, you cannot get one without the other, especially if you want to attract top talent. What do successful entrepreneurs do to get around this situation?
  12. Focus is important for execution, but having some flexibility is also good to not miss out on new revenue and market opportunities? How do we balance between these two?
  13. What recommendations do you have to hire your first 5-6 people on the team?
  14. What are three things you will do different if you started a new company now?
  15. Do you have Mentor(s) and how have they shaped your journey to what it is today? May be I can learn something from your own experiences.


There may be hundred others specific to your idea or the stage you are in. What draws world-class mentors to want to work with mentees like you is:

a) Quality and clarity of your questions

b) Genuineness in your voice

c) Passion you have for your idea

d) Willingness to listen and change your ways

e) Accountability and responsiveness to follow up and provide updates

f) Gratefulness

g) Paying it forward to others by sharing what you learned with others.


See you all at Tiecon 2013.



  1. How would you identify the right market fit at early stages of your start-up? Without spending a lot of time and efforts on building MVP’s, is it possible to identify the right market fit?


Please enter your comment!
Please enter your name here