Thoughts from a "failed" entrepreneur:
I think I worried so much about failure that in the end I failed. I worked my butt off for eleven years -so much that I was so burnt out that I felt I had to shut down my company because one investor, then another, stopped believing. Yet, I still believed! I fought so hard to avoid the exact outcome that eventually came to pass. I did not want to be the one that "closed it down". But know what?! I survived. I learned a lot. I am grateful for the experience. And, I am proud of what we accomplished! No one can take that away.
I wrote this note to myself one evening in the depths of despair shortly after closing down my award winning social venture business (some referred to it as abandoning my "baby") after 11 years...
I am sharing this here because indeed entrepreneurship FEELS lonely. As the leader, there are things that are hard to share with staff, investors, board members, family, friends etc. Note the word "FEELS". I agree with all comments above to seek confidants wherever you can find them. Like personal friends and family, extend your network beyond the obvious choices so that you an decide who you can go to for which conversations.
Shortly after I wrote this note to myself, I sent an email to my "network" letting them know of the decision to close the business. The outpouring of support from my network (near and far) was incredibly cathartic. I had no idea how much support I had along the way. It was always out there, but I had failed to believe in it - instead focusing on the "loneliness" I felt at the time.
Try not to let the loneliness overpower you. There are people out there that may not be able to help you directly address your challenges, but they may be will more than willing to be a sounding board! Just look at this community - people do want to be supportive of one another!
Keep on trucking! :)
Gathering a good executive team and advisors you have a rapport with is crucial for sure -- but if I hear you right, Saurabh, you'd benefit from people outside your company.
I've never been without an informal group of 4-5 fellow startup founders, that I meet with monthly. One group met consistently for 8 years before it disbanded. My current group of 4 has been meeting monthly for 2 years. In essence we're an ad-hoc "peer advisory board." We met at various networking events and decided to form our own group. The business, leadership, and personal support I get from them is simply unparalleled.
They've been where I've been and are going where I'm going. They understand the challenges like no one else in my life does. I can talk to them about sensitive confidential stuff I can't discuss with my team. They've also made crucial introductions, helped steered me from people who might not be what they say they are, and are deep wells of resources and insights relevant to my job. In some ways I'm closer to these folks than my closest friends.
Our meetings are casual -- we gather at a booth in a bar. We each take 20-30 minutes to check in and discuss something we're dealing with. We use a private Facebook group to share resources and get support in between meetings. And we get out of town together for a weekend retreat at an AirBnB once a year, where we can stay up late, get drunk together, and share the personal stories that fill in the gaps of our business stories and strengthen our rapport.
You'd find your peeps inside your current network and at networking events. You can start by reaching out to a founder you've always liked, invite him/her for a drink and toss this idea pass them. Each of you could then pick one other person to join in and you pick an evening each month that you can all commit to. I'd recommend the group stay under 5 people, because you'd each benefit from a 30-minute turn each month, and recurring monthly meetings that last longer than 3 hours are untenable.
Hope this helps!