Ask HN: How do I look for an experienced mentor for doing a startup venture? | Hacker News Reader

Ask HN: How do I look for an experienced mentor for doing a startup venture?

21 pointsnyrulez21 comments

I recently quit my job at Google to pursue something I've wanted to do for many years. After 2-3 months of messing around with ideas and code + reading up a lot, I've come to the somewhat painful realization that building a product and writing code is very different from creating a sustainable business. While I'm determined to do what it will take, I think that alone won't compensate for product fit/business/growth related mistakes where I have little experience.

I also feel doing this without a good experienced mentor will cost me 10 times more effort and pain but I'm not sure where to start. Has anyone done this before and have any tips how should I go about this? Ideally this would be a fruitful relationship for both where the mentor can see their mentorship making an active difference for a nascent venture and experience some joy in its success.

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As a somewhat experienced CEO it sounds like you're asking for something for nothing. You get the financial gains and the mentor gets to feel emotionally fulfilled? This is business. If you want people invested to the point that they're making a meaningful impact you need to compensate them and bring them in full-time.

Furthermore, it sounds like you've encountered the biggest challenge a CEO faces which is how to successfully go about talent acquisition. To me it sounds like you really should be looking for a cofounder.

If you're dead set on mentorship there are CEO mentorship groups out there such as Vistage. I've never attended but I can imagine it's useful.

Are you suggesting an advisor? I guess mentor/advisor are the same thing and I am definitely open to any kind of value sharing - but the question of finding a good person to advice you remains :) I'll check out Vistage - thanks for the reco.

I am looking for a non-tech cofounder but I feel it's not the same thing. Why would a successful entrepreneur who is already running a multi-million dollar company leave everything and become a full time cofounder for a first timer and unproven venture?

I'm suggesting focusing on a cofounder instead of an advisor.

No one would leave a successful venture for an unproven one. But there's lots of serial entrepreneurs who have already exited and are floating around looking for interesting opportunities. Your startup is niche so I'm not sure you'd find someone with relevant experience that easily.

This is unsolicited but my strategy if I was in your shoes would be to talk to people whose services you would be replacing. Those would likely be the Wall street investors. Get honest feedback early if your product could compete with their services. At the end of every discussion you have ask them if they can give you names of anyone else who might be interested in seeing your demo or potentially joining you. In other comments you say it's too early for VC...that may be true but getting introductions and asking for introductions to potential cofounders could be very fruitful.

You have a really impressive pedigree so I would always lead with that in any conversation. I'd also update your LinkedIn to reflect what your accomplishments were at Google instead of what your department achieved. Add your new startup to your LinkedIn. It's work but I'd also recommend getting professional headshots taken for your LinkedIn. This stuff is important. It's not because people can't see through it...it's because it's a negative signal if you don't do it.

Thanks - this is quite helpful and appreciate the kind words. You're right - I have approached some targeted folks for co-founder and it's been harder for this kind of domain. The other issue is that unless it does something (apart from claims), it's harder for some folks to wrap their head around the value prop, see it's actual use and get excited about it.

I am trying to get to a usable working version this month and then I will start contacting more folks as you recommend. The search engine is designed to be complementary so it gets layered on top of other ways people are used to looking at the stock market.

I have spoken to many in last 1-2 months and have learned a lot from them. At some point though I feel discussions aren't very productive if there isn't a clear product/service to talk about. It has been a tough balance to strike - ton of discussions with potential parties vs actual product building at this early stage.

Hence the search for a good advisor/mentor to help me prioritize different things well and not make mistakes as an engineer. The advise here is helping though :)

When the student is ready, the master will appear.

For the most part, I find it best to find mentors who are only slightly ahead of you. Someone just learning to write wouldn't want to get tips from Shakespeare.

If you're still in the product development stage, you'll want to get a mentor who has reached the scaling stage, but not necessarily an "experienced CEO" who has exited a company. I looked for some of those and they told me "You can't do anything with ten thousand dollars." It's not that they don't want to help, but they can't recall solutions or even think of any, and many of them grew up in different eras.

However you have to offer them something. Even if it's an emotional gain, there has to be a reason they would pick you over some other kid with a landing page. You have to prove yourself committed enough.

The higher level mentors might invest in you. The lower level mentors might see something about them in you, or just want someone to bounce thoughts off. A lot of people have theories about the nature of startups, and you should be the canvas for them to experiment with and run their theories on.

I agree with all of this. But the question I asked remains :)

You can just cold email them or connect on LinkedIn if you meet the prerequisites. It's much like asking someone out on a date. Mentee often makes the first move.

You should provide more context.

Are you still whiteboarding what it is you'd like to sell, have you built something but haven't sold it, have you sold it but it isn't getting the traction you assumed it would get, etc.?

If you quit your job and are not willing to take up being an independent contracter to pay rent/etc. while pursuing this dream, then how long are you willing and able to work on this full-time before needing to bring in additional income? That is, what's your timeline for making this your primary source of income?

You sound like a technical founder without a non-technical founder. Do you have other technical founders?

I ended up throwing together some material, from my MBA course on launching a new venture, for someone on HN, and a surprising number of people emailed me asking for said material. Email me at anongraddebt@gmail.com if you'd like access to the materials.

I have a clear idea of what I am building (based on lot of real life discussions and a bit of iteration) and have an internal early version (https://stockquanta.com). Nothing sold yet. But I have also been talking to folks and based on what I've seen from my network trying to start ventures, most of these ideas (Good or bad) end up biting the dust. I'm trying my best to avoid the same fate. I've seen 1 venture out of 7-9 in my network succeed. I can survive for a year from some friends/family funding but it's too early for VC.

Everyone is suggesting co-founders and I am definitely trying to find the right fit for that. But none of these will be already hyper successful entrepreneurs, I think :) Hence the question about a good way of finding an experienced mentor who probably wouldn't be interested in leaving their successful company and being a co-founder for a first timer unproven venture.

Thanks for the advice - I will email you.

I hope you'll find the materials helpful.

Here are some quick initial thoughts for your website:

After I scroll down, download your white paper and open it, I find the clearest statement of your value proposition under Mission Statement.

"To democratize Wall Street Investment Technology for mainstream investors and make it super-affordable. So that all mainstream investors can benefit, not just Wall Street Professionals."

That could be reformulated to be cleaner and better sounding copy and put on the home page, as that seems closer to your true value proposition than anything I can find on the home page. On the home page, you try and draw me in with a description focused more on the features of your product. You talk about a search engine and finding lower risk investments, etc.

However, your value proposition (put in informal, conversational form) seems to be something more like, "Hey, I worked at D.E. Shaw and Google. Want to buy the same tools that quantitative traders use to make better investments than the average person? I know the tools and will sell them to you." Now, this would need to be reformulated to make better copy, but you catch my drift.

Will pretty much everyone who lands on your site know Google? Yes. D.E. Shaw? Most won't know who or what D.E. Shaw is.

Here's a simple set of A/B experiments to start with: Come up with a more accurate statement of your value prop., and the story you want to tell on your home page, and run different versions to see which gets more traffic. It may be that more average joes know Goldman Sach's than know D.E. Shaw. So, on one version of the site you are testing, you can try potentially more recognizable Wall Street names like GS.

This is cool - I appreciate you taking the time to think about this. And if you're an investor, I hope you find the guide helpful.

I like your ideas about making the mission more prominent, which I will do.

I have had this struggle in conveying clear benefits of what I am doing, in real life conversations. I find that when I go too meta, I can lose some of the more pragmatic and impatient users as their eyes glaze over, but it makes sense for more thoughtful types and even investor types. There is this distinction between user pain points, features, benefits and mission. I've mostly stuck to the duo of pain points and benefits, and delegated features and mission to other pages.

I like my mission of course :) but I don't know if users care about it as much as I do compared to benefits the mission provides. But that's where A/B will help as you suggest. I am going to pay attention to this along with coming up with a better copy. Thanks a bunch!

Here you go: https://www.ycombinator.com/apply/

I did earlier based on an earlier stage version of my idea :) I interviewed at YC last month.

You made the crucial mistake of leaping without looking in a era where looking is very cheap. (ie. You have no clue what you’re doing, you should have googled it.) I’d step back and ask yourself why you are doing this. Honest advice, if you’re dead set on doing a startup, join one as an employee, try to understand how it works as a business, and start reading the extensive literature on the field.

I'll bite. Are you suggesting that the domain of my venture is not well thought out or are you suggesting that without working for a startup (and not a big company), it's useless to do a startup?

My company has been quite successful building a network of advisors and mentors (in our niche). If you want to chat, feel free to email me at liamcardenas [at] gmail

I always like connecting with fellow entrepreneurs. I also might be able to connect you with a non-tech co-founder... if its the right fit. There are lot of them out there that /wish/ they could partner with an engineer!

Are you going to be raising money? VCs can often provide these mentors.

It's too early for VC and I have some early funding from friends/myself. I agree having a good VC on-board would be nice but I think I need to have some success for that?

yes too early for VC to fund but not too damn early to connect with VCs to see what their informed experienced view is..most VCs respond well to a bite to eat and some coffee

That's helpful. I can start exploring my network but is there a systematic way to reach out to them ? Cold-emails/linked-in?

Take a look at SCORE (www.score.org) and EO (eonetwork.org)

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