A Startup Journey: Need A Little Help?

Photo by Noah Buscher on Unsplash

For a startup founder, adorning your website and social profiles with a title like CEO, CTO, or CMO, or perhaps a fact like Founder, might feel really good. Just let it soak in — the title sounds soooooo good, right?

And it’s true. I mean, what else would you put there? Something related to your pets or hobbies? No, of course not. It’s what you do day in, day out — you build your company.

And building your company is not an easy journey. Everyone knows this, so as you tell the world who you are, you’ll get offers for a little “help” along the way.

Of course, the right help at the right time for the right price can be immensely valuable. Yet, there’s another side to that coin.

So, let’s consider what sort of help likely comes your way, often seemingly out of nowhere. Then, we’ll consider whether it makes sense to move forward, hang back, or run screaming.

What Sort Of Help?

Building Or Improving Your Product

With a title like CEO, I’ve found that many people will just assume zero (or less) coding ability. Many of my readers already know that I have an MBA, which further exacerbates the issue.

So, I get lots of offers from various sources to build MVPs, products, websites, and whatever else I might want to pay someone to build and iterate on. These offers come at conferences, over social media, and from people who have somehow figured out or otherwise acquired my email address.

Marketing of these services ranges from relatively benign to fairly aggressive.

For example, some vendors will hallucinate “fears” that I may have around outsourcing, and they’ll tell me that I just need to get over these fears and move forward in life. So, they’re part coding shop, part therapist.

As you might imagine based on some of the other posts in this series, that revelation was news to me. Fears, huh? I would have thought that having already built and launched the product and website would be the biggest hurdles preventing me from contracting with anyone to build the product and website, but I guess you learn something new every day…

Kidding aside, from my perspective, this hallucination foreshadows what it might be like to work with them. Will they hallucinate features? Will they hallucinate requests? Will they hallucinate my approval to share code with others?

On the other hand, some people take the five or so seconds that they need to read past the CEO title and realize that I can code, which might mean opportunities to sell other products and services to me.

Considering that I’ve built, released, and iterated upon several full-stack products, starting from scratch, I’m reasonably competent at frontend engineering and reducing user frictions. But, being honest, I’m just better with backend engineering. And mobile is just fun.

Honestly, looking a bit deeper, I’m obviously not a highly-trained graphic designer (this little detail didn’t stop me from designing and trademarking Next Mountain’s logo while immersing myself in 15 or so graphic design books for a few weeks; if you’re looking for recommendations around logos, Logo Modernism, which is huge and heavy, is probably my favorite, but many books by Yasaburo Kuwayama are worthwhile, as well; for graphic design in general, a book that I still like is The Non-Designer’s Design Book (4th Edition), which is a great place to start and has something for everyone).

And, I like using Bootstrap as a base for styling websites and apps. It has a lot right out of the box, in my uncertified-graphic-designer opinion. I don’t write all of the (S)CSS/SASS/LESS/… from scratch, lovingly twiddling every fractional rem to specification (but I do optimize some of them, as needed).

So, naturally, I get outreach for things like the “one thing that I’m completely missing and need to change on my site to totally change everything for the better and make it amazing from a design perspective” or whatever, as well as for mocks and wireframes.

As a startup founder, you could expect to receive the same. Now, before we delve further, let’s finish up with the high level help buckets.

Marketing Your Product

We just noted that I’m probably not going to take your graphic design job. You can breathe another sigh of relief as you realize that your marketing job is probably safe, as well. At least from me.

But as with graphic design and user interaction/user experience (UI/UX) considerations, I jumped into tons of resources (I also have an MBA, but I’m stronger on the finance, management, and strategy sides; marketing is deceptively difficult, and its challenges shouldn’t be underestimated). In particular, I dove into a veritable cornucopia of blogs, books, courses, and other resources.


I do this because it’s in my nature to overcome whatever challenge presents itself, but it’s also part of the reason that I founded a company and have been building everything from scratch — to get experience on all sides of my business and to be an educated consumer, if I do choose to outsource or contract out anything.

I’m also bootstrapping, so every cent that’s spent matters. If I contract something out and waste funds on a zero or negative value item, then that’s a problem.

Now, to be helpful :), here’s a quick aside for anyone like me who might be looking for marketing references: You might consider the Advanced Marketing Program (AMP) by Neil Patel. AMP is is a big program, covering sales, marketing, advertising, metrics, etc., and if you decide to sign up for emails, then I’m pretty sure that you’ll get a webinar invite… At this point, it’s getting dated, but they have an active Facebook group and weekly calls. It’s also worth considering pretty much anything at Copy Hackers. Copy Hackers also happens to market email marketing and copywriting via, well, email, so sign up if that’s what you want. There are tons more resources that you’ll find if you start looking into these products.

But let’s get back to the main thrust of the article.

Earlier, we noted that people who want to sell me coding services often anchor on the business side of my background. Based on the technical side of my background, I also get interesting outreach from marketing and advertising service providers.

So, I get outreach about various and sundry things, including long marketing copy about driving user growth, contact about providing herds of followers, and generic marketing-related outreach asking about my “struggles as an entrepreneur.” What are they? Just tell us…

Struggles. Struggles… Struggles.


I don’t think in terms of struggles.

The word doesn’t resonate.

The word “struggles” evokes images of a fussy two-year-old child figuring out the whole shoe tying thing over the course of three hours.

That word might be right for some, but not for me. And, a key lesson in the programs that I mentioned above is that a good marketer knows their audience inside and out.

Speaking in words that don’t resonate with the customer doesn’t display that knowledge to me. These providers may be extremely successful and talented, especially with someone for whom, or in some market in which, struggles resonate, but it’s unlikely that I’ll ever find out.

So, let’s move on to a catch-all bucket, and then we’ll consider whether the help makes sense.


I’m going to be a bit lazy here and lump most everything else into an “Other” bucket, since I value your time and mine. These items include

  • Offers to buy or sell your company (this is an important consideration and one that I ran by Next Mountain’s corporate attorney; a good attorney can be very valuable)
  • Mentoring and advice from current and ex-entrepreneurs, as well as investors and business luminaries
  • Bookkeeping, tax, and other services (speaking of that, Sept 15 is coming up soon for anyone who filed for an extension or two…)
  • Fundraising help, including offers for you to pay to present your company to potential investors at conferences
  • Pitch deck preparation
  • Legal and compliance services, including GDPR, trademark protection, etc.
  • Translation services for your websites and apps
  • Interns and people who want to be mentored (yes, it’s an offer for you to serve as a mentor)
  • Funds, as equity investment, loans/debt, or otherwise (what are friends and family really giving you?)

, and so on. These offers come from time to time. You may not have even considered them, but there they are.

Instead of dwelling on everything that might be possible, let’s consider whether any of these offers might make sense.

Should You Engage?

You should consider this question fully before receiving outreach and offers. Otherwise, it’s just too easy to jump into a relationship that can be full of gotchas and cost a lot of time, energy, and cash.

I know, I know — move fast, iterate, be lean, and so on.

But you can still think things through.

Consider The Economics

Mathematically speaking, P(getting screwed|engaged in some transaction) > 0, which is read as “the probability of getting screwed given that you engaged in some transaction is greater than 0.”

This equation simply states that there is a possibility that things won’t go well — you might not get screwed in the transaction, but then again, you might.

You can find many, many examples online of this being the case. And there are probably many, many more examples that aren’t online.

Yet, people in startup circles often dismiss the MBA and other business-related degrees as valueless. But they really aren’t, because these degrees provide useful viewpoints regarding economic choices. And startup founders are faced with thousands upon thousands of economic choices.

Whether you should choose any of this help boils down to a probability-weighted estimate of the value that you’ll receive minus the value and resources that you provide.

Wait, what?

In other words, is this help worth the energy and expense?

Even more concretely, if you commit $X to some transaction, where $X also includes estimates of time and other resources spent, did you get $X or greater in value for doing so?

The value that you get from outsourcing or other help could include additional revenue, better market position/share, some clear competitive advantages, knowledge from mobile or other product MVPs that will somehow inform your decisions, and time that you are freed up to work on other things. It could just be good advice that helps you avoid an issue.

Let’s consider a concrete example. If you have an idea and pay say $250,000 for a working prototype, website, and basic mobile app, while spending 10–25 hours/week managing that project over the period of several months, testing what the team delivered, and so on, then did you get at least that value in return?

Did you get to market quicker, with a better product, for whatever you spent and invested, than you could have done on your own?

Was the investment worth it?

Making An Informed Choice

OK, fine. Maybe you can’t code, you don’t understand accounting (is that a debit or a credit? wait, but that seems backwards…), you can’t conjugate verbs or string a sentence together, or whatever the case may be. These are problems, and I get that. But there are a host of options for getting the each of these done (technical co-founders, outsourcing/contractors, interns, advisers, etc.), so you still have to choose one to go with.

I’d encourage you to consider where your time is being spent, where your challenges/struggles/issues/… lie. Really be honest with yourself, and consider your goals, aspirations, and frustrations. As well as your resources, and what time and money you can spend.

If you find a clear lever that can provide you with more value, then start looking for the right person or service provider. Try to understand what the total commitment is (revisions are rarely free). Try to estimate what might make sense. In my opinion, this would be time very well spent.

Another way to proceed is to ask a more nuanced question. Should you engage now? Why is now the right time to do that? Does engaging make much more sense further down the road? Or, has the time already passed you by?

Any way you choose to go, it’s worth considering your actual needs, beyond the possibilities presented in the marketing. It’s also worth getting educated on what you’re buying or contracting for, since it’s easy to spend a lot of money and wonder what you paid for.

Wait, Don’t End The Article Yet, Because What If It’s Free?

It was free, was it? Oh, yeah? But was it really?

Did you have a contract? Or, did you have a contract and not even know it? Or, did you just inadvertently get a co-founder?

Contracts matter, and you can enter into a business relationship without meaning to.

And this is another good thing to think through and perhaps get advice on. I mean, if you don’t have access to an attorney, then at least read The Entrepreneur’s Guide to Business Law, 4th Edition. It may be the most fun and readable book that you’ll ever find on legal matters, while also being highly illuminating for you.

Good luck!

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