Technology Startup: Loneliness

I'm 1.5 years into building a Healthcare IoT product in an 80/20 venture with my co-founder. The deeper I go into building the business, the more intense and complicated things get, the more isolated I feel. I have my grandfather who was an entrepreneur in his time and he has been a blessing. I have an amazing wife who has been an angel through this journey. My co-founder is one of my best friends and our working relationship is great, but he's 20% in (moonlighting after FT job) and doesn't spend 95% of his waking life in this head-space like I do. He's vowed to quit his job when we hit paydirt but until then, I'm largely alone. It's on me to generate my own energy (and for all of my contractors), do all of the critical thinking and stomach / burn-off all the emotions associated with the process. Even when he does come on FT, he only has a silo'd 20% context.

I understand that this is entirely my own doing. I just wonder what the future looks like. I don't see myself / my person becoming more relatable to the broader population as I go down this path. Maybe in the future I need to move to SV, Austin or NYC because there's people like me really doing this out there? Maybe in the future EO / YPO has the people I'm looking for?

For context, we just put a bow on a product we can sell, we're finalizing a case study with our pilot customer and we just started actively reaching out to sell our product September 1st. The mental transition from product development to sales has been brutal (i.e. being in complete control to influencing the best you can). This definitely feels "darkest before dawn" but there's going to be more of these episodes...

Any advice from those further up the path from I would be much appreciated.

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Oct 3, 2021 - 6:22am

Eventually you'll build out a solid network of people like you. Starting out, early twenties were rough but after 24 or 25 it improved a lot network wise.  

Some I met through EO and YPO, some cofounders and ex-cofounders. Others are people I've invested in and vice versa.

My fiancé is always surprised by how many friends I have in cities when we are visiting but these friends are usually financially bound to me in someway so I am not sure where the line sits between friend and associate? I consider them friends and I'm sure they do too; our relationship is much stronger even if we don't talk much because I am managing a significant chunk of their life savings.

The real problem with being a noob entrepreneur is that you have no idea if you have 72 IQ and will fail horribly or know what you're doing -neither does anyone else until you have traction. This makes it much more difficult make friends with true entrepreneurs that have built real enterprises. Personally, doors started opening up once we hit about 15mm or 20mm rev. 
 

One other useful place might be industry specific meetups or groups with prerequisites? I'm actually in one that Patrick is in too lol. It's been awesome and I've made friends with a few guys who have cos doing anywhere from $20mm to $100mm. Helped two pick out an iBanker and ran them through the process etc! They gave me some great operating tips too and will likely invest in our next deal or the Series A for the co I'm currently stuck running. 

I would recommend getting into the capital game for sure. Invest in others or raise capital. The connections are worth it and equity is so cheap atm you have to be 100% crayon eater not to raise.
 

Other than that, I think your relationship with the cofounder is really important. I've never had a bad cofounder per se but my current cofounder is the most aligned I've ever worked with. We have not had a serious argument since we started working together in 2018 or so and he is just as dedicated to the work as I am, even before it was clear the co would work. So glued together at this point that his wife can't tell us apart on the phone. 

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  • Director in CorpStrat
Oct 3, 2021 - 11:32am

Thanks a lot for this reply. I think I'm also hearing a toughen up for the time being from you as well. I like the picture you paint with the business associates / friends. That would be enough for me.

LOL @ the 72 IQ -- so true. I look at 90% of the shit coming out of YCombinator and truly believe they are stupid business ideas with wannabe entrepreneurs. I say that but those clowns are raising crazy amounts of money with their jack-off products and I'm over here with my dick in my hand. If I had a nickle for every time I heard, "You're building your business the right way"... My co-founder and I sleep really well at night because we ate shit for so long on product development vs marketing. But I swear if you're willing to lie, cheat and steal with marketing, there is a path of less resistance to making it to the next level.

We do plan on raising when we get to $5K/MRR. I've personally bootstrapped the entire operation and I'm not about to eat shitty terms now. These days I think there are so few early-stage technology companies that just show up to VCs with a healthy balance sheet. A proven entrepreneur told me that he's done this twice and has had 10+ VCs fighting to get into his round and that this is the way to go. But fuuuuuck do you live a lonely existence until then.

Without giving too much away, I don't meet anyone even remotely my age at industry specific meetups. For meeting other "like minds", I think meeting with other "founders" at my level is a waste of time as they are not "real". I meet none of the prerequisites required to join any of the organizations where I think there are individuals of caliber. Now I'm really starting to sound like a crazy person hahaha! Seriously after reading your comments and talking to my grandpa, I'm going to stfu and keep grinding because there is nothing worth picking my head up for at this point.

I hear you on the co-founder and I'm happy that you have found that in your current partner. I truly believe I have that in my current partner as well. Sometimes it sucks that I'm alone in this head-space and I resent him for not being here but then I remember that's not the circumstances right now. It's on me to flip the economics of the situation to where it makes sense for him to leave his FT W-2. I'm going to stop writing now because what I need to do is blatantly obvious but this has been cathartic. It really has.

  • Associate 2 in PE - LBOs
Oct 3, 2021 - 12:51pm

I'm going to stfu and keep grinding because there is nothing worth picking my head up for at this point

Look man I'm not an entrepreneur but one thing I do know a lot about is the negative affects of loneliness, particularly in a society where male loneliness is endemic and there aren't really a lot of great outlets for men to make friends. You have to do a few things outside of work to get into a good headspace, too, like finding sports / mutual interest groups with other men. You can Google male loneliness and get a bunch of garbage articles from Men's Health, or you can search it on Spotify and get some really solid podcasts discussing why this issue is endemic to our current time / place, or you can find some scientific research (up to you) but I encourage you to look into it because taking care of your mind is a crucial component of having an edge as a founder (notwithstanding simply being healthy).  

Edit: notwithstanding simply being healthy and happy

Oct 3, 2021 - 2:02pm

That's the thing, you can raise without eating shit terms even with $0 in revenue. Loads of companies raising at $10m+ pre without revenue. 

Keep in mind once you're at Series A+ you can start liquidating stock via secondaries. This is where you make $$$ in entrepreneurship during a hot VC market, far ahead of an exit. :)

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Oct 4, 2021 - 8:52pm

Here is one of the best resources I have personally been given while trying to raise. Sahil was "temporarily" interested in my company and he directed me to this link and I find it very useful. (Did not raise from him)

https://shlcap.notion.site/The-rest-of-your-round-c3847117e71045beb4857…

He gives you lists of investors, the size of companies they are looking for and the check size they write. Hope this helps. 

  • Quant in AM - Other
Oct 4, 2021 - 9:44pm

I really want to ask you some questions on logistical aspects of bootstrapping a start-up I know it's out of the blue, but can I DM you?

I might even ask you om this post if you don't mind. My questions are fairly general - incorporation, when to look for funding, etc...

Oct 3, 2021 - 11:46am

Moving to a different state so you can connect with people, what is this 1973?

Theres a place called the interweb machine, I think. You can use it to connect with like minded people who are going through the same experience as you.

You need to develop more mentoring relationships. Both mentor and mentee. That will help you immensely.

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  • Director in CorpStrat
Oct 3, 2021 - 12:17pm

You say that shit like I'm not posting on WSO (a website, hosted on a server, connected to the internet) looking for advice.

I had a long retort about how nobody wants to mentor a "noob entrepreneur" but your overly simplistic, broad sweeping comment on mentoring gave me the idea to reach out to the guy who gave me the 5 warm introductions to prospective clients. I should deepen that relationship and ask for more guidance.

And for that, sir Marcus_Halberstram, I thank you.

Oct 12, 2021 - 8:09pm

Would probably:

1- focus on tech/start-up communities, not finance ones. You're fighting for your life to launch a start-up not trying to get a job in investment banking/PE.

2- almost everyone is willing to mentor others. It's not your station in life, it's your approach and energy you're putting out there. Why don't you mentor as well as try to be a mentee? Maybe you'll see what you can improve upon in your own approach.

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Oct 3, 2021 - 1:41pm

OP I'm literally going through the same process, 100% bootstrapping, full time, same long timeline vs. what I expected as it's evolved with more buildout, insights, and tweaks to execution strategy-as you are learning more of whats important as you go - including on the legal risks side- IP trademark copyright. But more so related to the creative process, building something from scratch.

Love sharing my vision and areas I see as untapped opportunities- but it's tough to find like minds + ppl with enough knowledge of the space to give a view. The problem is - very few ppl truly are a visionary / have vision. I'll stop there bc you declined that other guys offer to DM & discuss more, so I'm prob wasting energy. But if you wanna at a minimum introduce ourselves, happy to.

  • Quant in AM - Other
Oct 4, 2021 - 5:19pm

I'm much earlier in the path but I wonder if I will ever feel this way... 

I had this idea half a year ago. Spent 3 months just trying to find the right people to work with & flushing out the idea. Then I spent another 3 months just understanding the nature of the industry and the market I'm trying to go into. I mean really really understand - the pain points, market segments, current solutions and where they fit in to the value chain, nature of competition, and finally trying to understand and come up with what would differentiate us.

We just finalized what our differentiation is going to be and the strategic vision that would dictate our goals for the next year or so. We also have an initial design of the product and a strategic roadmap. We're intentionally keeping things a bit fuzzy but we do have a tangible mission statement. We did some de-risking and made some backup plans based on couple of the hypothesis we've discussed. (I guess you can call this pivoting or finding product-market fit). But who knows, we might have to throw away all that because step 1 doesn't really work.

So far, I'm loving the complexity of the problem and geeking out on how we can build it. I have such a strong conviction we can make it work. But reality hasn't hit yet....

Damn that reads like an unorganized jumble of a thought.

Oct 4, 2021 - 8:37pm

Currently working at a startup and I can definitely agree that one moment you feel like you are doing something great and changing the world and the very next day you feel like you have wasted months working on your product due to a minor setback. 

I'll advise you to look at it from the journey perspective rather than the end result. Even if you fail it is a learning experience. You also learn a lot about yourself when you face failure.

In my startup, there are literally little fires everywhere, and I just have to deal with the biggest fires I can put out. I fall asleep at night knowing fires are burning and getting bigger. It is hard and it is stressful. You just have to keep going.  

Do you have an MVP yet? 

  • Analyst 2 in IB-M&A
Oct 5, 2021 - 8:46pm

OP - I raised at $10mm pre-rev for my first venture (ignore title), and you are doing this the right way. As soon as you accept external capital, you are on the clock. Your investors will expect you to deploy the capital you raised to grow the business. This can be destructive before you have reached PMF, because you will begin burning cash before there is enough of a tinder box to ignite with it. Simultaneously, the longer it takes you to find PMF while on the clock (i.e. after raising a round), the less of a priority you will be for your investors. Together, those two results are obviously the makings of a sub-optimal outcome. Moreover, that kind of experience would detract your focus from finding the PMF that is at the center of your success, and it would likely further strain your relationship with your Co-Founder.

I am not one of these jaded "don't raise VC money" Founders at all. VC money is great, and aligning a bunch of powerful, wealthy, wise, and helpful people (who are often former founders too) around your venture by adding quality VCs/angels to your cap table is a no-brainer when the time is right. The time to do that is when you can look at yourself and your venture in the mirror and honestly assess that you have a flame going, that you are succeeding at growing it yourself, and that VC capital would serve as lighter fluid, rather than as a futile spark.

At that point, you will be in a substantially better position to carefully choose your cap table, rather than hope investors choose you. You will be in a position to win.

On the loneliness point, I don't really have any good advice, but I can totally empathize with you. Being an early-stage, pre-PMF Founder was the most challenging, isolating, self-doubting period of my entire life. At times, it can be truly brutal, and I'm sorry you're experiencing some of that. One thing that helped me during the gulf between when I started my company and when we reached PMF was reconnecting with the initial passion, excitement, and confidence I had when I first started the company, while simultaneously leaving behind the naïveté that came with it and applying all my learnings during the interim. You are likely much "smarter" (in the context of your knowing your business and charting a productive course to PMF) now than you were when you started your business, but you are likely also a bit burnt out - I surely was at times, and it's only natural. Try to zoom out, refresh (sounds radical, but if possible, take a couple weeks off; go somewhere and try to completely reset - this will become harder later in your company's lifecycle/as you grow, get investors, etc.), refocus, make sure you are prioritizing the right things to achieve PMF, and then keep marching. Best of luck - hope you're hanging in there, and I wish you all the best with the venture.

  • Director in CorpStrat
Oct 6, 2021 - 12:52pm

The time to do that is when you can look at yourself and your venture in the mirror and honestly assess that you have a flame going, that you are succeeding at growing it yourself, and that VC capital would serve as lighter fluid, rather than as a futile spark.

I love this perspective on VC Capital. Pundits says it takes 2 - 2.5 years to develop and bring healthcare technology products to market. We're way ahead of schedule and it makes me think that I can "cheat" by raising without having found PMF. I would use the funds to pump LinkedIn B2B ads, more mature marketing collateral and polished enablement materials, but I can do all this things without the funds (albiet, slower / smaller scale). We've resolved the best course of action is proving out our B2B GTM strategy at a really small scale to catch footing ($5K/MRR) and bringing that to a capital partner. Then a fucking monkey could see the trajectory because the entire puzzle has already been completed.

Small rant: Venture Capitalists don't actually give a shit about product. I don't care how much "vertical industry expertise" they tout, they view every product as a generic widget. Technical complexity? Novel features? Industry innovation? Fuck you, your 1.5 year old business is in the same bucket as the Twitter Engineer's 2-month-old CRUD SaaS application because you're both pre-PMF.

Thanks for sharing your mental as a pre-PMF founder. I feel great again. Antithetical to what all the mental health advocates preach but I've had the most success beating the shit out of my negative thoughts with rigorous exercise, loud music, weed and alcohol. I've only looked back on my progress once (after I signed my first proof of concept client) and haven't done so since. I think it's dangerous. I could congratulate myself on how "smart" I've become over the last 1.5 years but on the other-side of that coin is a massive opportunity cost. I'm going to keep the blinders on until I know I'm not going to die.

I debated even posting this topic (soft AF) but comments like yours have made it well worthwhile. Thank you for your taking the time and I wish you the best as well.

Oct 14, 2021 - 2:50am

Founders / Solopreneurs in the process of building your company from scratch - I think it would be valuable to connect offline + have dynamic conversations of things we learned along the way that can help each other, provide support, and potentially - friendship who knows.

Personally - I'm a basketball guy (turned football - WR/tennis/ping pong guy) that's elite at Mario Kart/Mario Tennis/Golf/GoldenEye 007 Proximity Mines in Complex/Temple, & have beaten Donkey Kong Country in 56 min. I am dying to find someone to play 1 on 1 in any of those arenas, but it's tough to find ppl that wanna compete. (This is me growing up - 100s of times practicing every 1 of MJs moves

). Hardest move to master was the jump stop+180 spin over Lambeer.

My background is in Lev Fin (skill set = keyboard/Microsoft office/computer/formatting wizard) but I'm also creative In solving problems.

For me-if I wanna deep dive and learn about an industry + competitive landscape, or really any topic - there's a few ways I'd 1) source the data, but more importantly 2) "spread the data" ->converting what I call "unstructured data" into "structured data" for purposes of 1) efficiency 2) being able to analyze, filter in rows in Excel, sort, etc. So high level - that's the idea. Recent example to learn something Combined 39 company reports:

from: PDF - 414 pages

to: Word - 414 pages

To finally: Excel - 38 page database - 1 row for each company, 3 columns (#, Company Name, Details)

Another day - I'll maybe conditional format or search for key words or themes that come up - to be able to bucket those into their own columns (customer concentration %, barriers to entry, market share, EBITDA Margin %). Point is I'm not in a position to leverage the data, sort, filter, and add columns to further enhance it (company description, industry, EBITDA, leverage-whatever).

Happy to show you stuff like this in exchange for your insights, energy, ideas, and any strategic value you can voluntarily offer going through it yourself.

Appendix - few thoughts on "Unstructured Data", PowerPoint layout issues (probably a run on)

Once heard Steve Jobs HATED PowerPoint- never read why but my guess is it was "unstructured"-basically the content is separated into 4 quadrants (2 columns, 2 rows)-so extracting the data is a pain. Friend is a Machine Learning CEO - says they do a "columns analysis" to extract data in these situations - to try to form some structure to it. Small footnote but Layout isn't conducive to synthesizing efficiently in database format..

QoE report is an easy example that comes to mind. Before I learned myself what the heck this report's purpose was - I feel like this deck in general is the most unorganized bunch of data tables + text in pages to follow that kills any flow to it. Idk if its just Big 4 guys can't format or create presentations - but QoE formatting and layout to be able to tell a story is a pet peeve of mine. Anyone share similar sentiments?

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