How I work with entrepreneurs

Having been a founder who raised many rounds of capital, I know that raising venture capital can seem like a black box process.

To help founders understand how I work, I’m documenting some of my process here. I’m focusing on pre-investment – soon, I’ll write about our post-investment process.

My philosophy:

  • I will always respond – If you’re wondering how I’m thinking about the investment or how a meeting went, write to me.

  • I commit to treat your time like my own – I will not ask you to do an analysis or a special meeting if I don’t plan to take it seriously. I’ll put myself in your shoes before I ask for follow up work.

  • I will seek feedback – I send an automated email to gather feedback from entrepreneurs I meet with. I sincerely appreciate your feedback as we try to improve what we do.


  • Introduction – I prefer warm introductions and generally don’t respond to cold email. I always respond within 24 hours. This response will likely be to suggest a phone call or in person meeting. However, I will decline to meet in situations when I know it would not be a good use of your time (we have a competitive investment).

  • First Meeting – when schedules allow, I optimize for connecting sooner vs later even if that means that it has to be a phone call or a short meeting (less than 1 hr). I believe most entrepreneurs would rather meet sooner vs. later. At the end of this meeting, I will set aside a few minutes for feedback (I welcome direct feedback from you too) and my goal is that we end the meeting with a clear next step. That next step can be 1 of 3 outcomes:

    • This opportunity is a great fit and we will establish a next meeting and set of questions to answer in diligence

    • This opportunity is not a fit and I will share why

    • I need to understand certain aspects of your thesis better before giving an answer – I’ll likely ask for some help in answering questions

  • Diligence – this varies considerably with the size/stage of the investment, but the commitment I make is to never create busy work. I believe a fast “no” is much better than a slow “no”, therefore, I’ll only ask for materials when our interest is sincere.

  • Customer calls – I understand the sensitivity around customer reference calls. When I do these calls, I script out the questions in advance and will share them with you. I will also share the notes of the call with you so there is total transparency. Regardless of whether we invest, I want that customer to feel like they are a genius because they signed up with you.

Partner Meeting – if our discussions advance to a partner presentation:

  • We will do a call before the presentation to give context for the rest of our group, how they interact and what they will know about your company before you present.

  • After the presentation, I will get feedback from our partners and will aim to revert back by the end of the day. This feedback can follow a similar set of outcomes as stated earlier – either we’re in, we’re out, or we need to dig into something quickly before finalizing an answer.

  • I’ll tell you what the feedback is, what I agree with and what I don’t agree with. I value my partners’ feedback so their perspective often impacts the way I think about the opportunity; when it does, I’ll be upfront about that. 

Term Sheet – I optimize for thoughtful simplicity because in early stage investing, we have to live with whatever we do for a long time. I don’t want to spend a lot of time or money on legal work but want to be careful to not create downstream issues. If you have questions, just ask directly – let’s not let the lawyers fight things out while running up the meter!

I hope this gives a view into what to expect when interacting with me.

M13Gautam Guptam13