Pioneer Community Discussion - What is the biggest hurdle you face?
Shared by jackson · 383d ago · 46 comments

At Pioneer, we've seen thousands of companies in every industry imaginable. Each comes with its own class of obstacles. From the challenge of building new & untested technology, to raising funds for your first hardware prototype, to winning users from long-established competitors.

What is the biggest obstacle you expect your company to face? Especially interested in those you hadn't expected at the outset.

abhinavreddy · 375d ago

The cold-start problem. How to grow a network, when you don't already have one to co-opt.

minhphan · 353d ago

I wrote this guide collecting case studies on 5 ways startups used to overcome the chicken-egg dilemma a while ago. Hope it'll be helpful.

sole-fields · 374d ago

Nice. What's the platform? Visited -- looks like an index for Discord channels?

abhinavreddy · 373d ago


kendsouza · 383d ago

I believe the most important thing for any company is always going to be customer discovery. One might think they have a billion dollar idea, but if there are no takers for it, the rest is moot. Also the customers/users you talk to should really and I mean really need what you are building. If they are not desperate for what you are building (that would be your biggest obstacle) , you have to keep on iterating until you get to that product market fit for your customers/users. Once you are past this obstacle, and get traction, the rest will be easy after that.
With, even though I know the customer segment (Home Owner Associations) very well, I still want to talk to a 1000 decision makers in this segment and still listen to their problems and see that I have not missed anything. Only then I will know that I have understood my customer very well and I am past my biggest obstacle.

jackson · 383d ago

This is great. Beyond customers (which is a questionable framing, I admit!), what are the second order obstacles you face? An example here is if I was building boats to clean waterways and I'd already talked to potential customers / validated the idea with them, I'd need the capital to build a prototype and, this being my first project, experienced advisors. Whereas if I were building TikTok for dating, my barrier to entry may be influencers on my platform. Or, like NFT-gal below, a more efficient system for going regularly viral.

These are all things that, if achieved, would change the fate of the company.

What are those second order, destiny-defining obstacles you face?

kendsouza · 382d ago

Our company has 2 SaaS products.. RunPTO and RunHOA.
RunPTO has paid subscribers and starting to gain traction while RunHOA is just getting into the customer adoption phase.
From my own experience and SaaS perspective, every stage has its unique share of obstacles.
The first ofcourse would be a thorough understanding and validation of the customer's problem.
The second obstacle or series of obstacles encountered would be in acquiring various resources to give your solution shape starting with domain expertise, initial funding(bootstraping) and tech skills to build it with.
The next big obstacle would be in getting customer signups for your solution on a mass scale. And then converting them to paid subscribers is another big hurdle.
After that I believe would be reducing customer churn:).

Some things we just take it in stride. As we understand, it will just take time..

Funding: I have figured that getting to 1000 paid subscribers(RunPTO +RunHOA) will get us to a annual gross revenue of around $400k.. we will be in great shape then. Getting funding at the early stage (without traction, this is difficult) will be great and we will reach our targets faster. One VC has told us he wants to buy us out if we reach 1000 subscribers. Don't think we need him then:)

Mass awareness of our products in the niche we operate in:
For RunPTO , some of the RunPTO keywords are on page 1 of google which helps us to get customer signups organically without spending a dime on marketing.
For RunHOA, building & spreading content(grunt work) is in the works. Maybe a year or so before RunHOA gets some traction on google search.

builderseller · 367d ago

I can't sleep well.
I believe there are three reasons behind it:

- I almost run out of money.
- I miss my wife and child. They live in another city, while I stay with my parents.
- My mother might have cancer. She will undergo medical test next week. According to the doctor, the probability is not high, but my mother has complex medical issue. So I am very worried.

The third problem is what frustated me. If my mother is OK, I would move to my wife's city and work there. Money problem is OK because I don't spend much. If my mother has cancer, I might need to get job to provide her monetary help.

Now I can only pray, even though I am not religious.

sam@novamoney · 357d ago

Tough life life, you're a real hustler. I wish you the best!

Miriam_Dorsett · 351d ago

Pray can be powerful as well as counting your blessings, focusing on what is working and going well. These problems are real life, and should not be ignored. Not sleeping well is something that I suffer from too. You are not alone. Just keep pushing, try to do at least one thing a week to move forward. You are exactly where you are supposed to be on this journey, and taking a pause does not mean you failed. Try snuggling puppies or other animals. Also crying is ok. Also spending time in nature can be good or doing art for me.

minhphan · 353d ago

Life is tough, but so are you. Hope you all the best bro.

oras · 378d ago

My challenges are:
1) My product covers 2 segments.
a) Companies that don't know how to write job ads/job descriptions.
b) Companies that have job descriptions and looking to optimise them to be more inclusive.

Currently, the product is mixing both. I don't want to waste few weeks developing separation when I still do not have many customers. I prefer to get more, understand how I can improve the product for them then decide.

2) B2B sales is a long process.
I am trying to learn how should I plan my time between prospecting, demos, posting updates and development.

What I am doing is writing down every single task I do during the week. Give each task a few meta info (simplicity, expected impact, actual impact, time consumed and justification). I use this to reflect at the end of the week to see which tasks were more important than others.

I learned this technique from a YC talk:

NFT-gal · 377d ago

Oo interesting technique. Has it worked fo you so far?

oras · 371d ago

It has been great actually. I always look back and review the list on Sunday morning to see what I have accomplished during the week.

Gabi · 378d ago

Something I find challenging is learning to sequence/ prioritize what gives you the most leverage and figuring out when the right time is to x versus y.

I'm trying to develop my ability to think strategically, manage and prioritize my time and then execute like a boss. I find that I get tripped up when I context switch too frequently-chunking time/ makers schedule helps manage this and having OKR's, KPI's and keeping existential thinking for the weekends only, really serves me.

If anyone knows of ways to develop one thinking/ decision making/ strategic thinking (less reading more practice type setting) that would be amazing!

kendsouza · 378d ago

How about less thinking & less decision making?:)

One of the ways would be to adopt a minimalist & simple life. You don't have to give up everything.
But scaling back on the things you are attached to will have a cascading effect of less clutter in your head and the space you live in leading to less stress and more clarity in your thinking and fewer and better decisions .

Steve Jobs wore the same black turtleneck, blue jeans and sneakers every day.  No thinking on the clothes he needed to wear and one less useless decision he had to make everyday,

Gabi · 378d ago

Hey Kendsouza,

Thanks, for the input! I already try to do this.

I'm the type of person who owns 3 pairs of the same jeans and 5 of the same t-shirts and other than the running shoes I only have 1 other pair of shoes. I wake up at 5 am and do my thinking/journaling before the day or taking other input before I start work.

I unsubscribe to junk (very deliberate about what I am thinking about/ exposing myself to). I have a morning ritual that includes cold showers, coffee making and walking my dog. I exercise daily. So I think I have routines down/ have spent years trying to eliminate useless choices (if you have more ideas -please let me know).

I only spend time thinking and deciding what to do in my designated portions of the week (literally I have structured thinking time in my calendar, tools I use when I do this). So I'm not sure it's about doing more or less but rather of how to do this better and what activities of things could I do to increase my learning/ ability/skill in this regard. ie Since scheduling structured thinking time and being super disciplined I have gotten way better at it!

Sal · 377d ago

Impressed with the discipline. Definitely a point of weakness.

Feel like discipline is learned by pressure. Maybe just haven't optimized the cooker in the right ways.

kendsouza · 377d ago

You have adopted a great lifestyle.
Just one more not react to every thought that pays you a visit..including thoughts about thinking:)
It is much easier to let most of the thoughts just pass by.

Sal · 378d ago

Love this answer. +1! · 383d ago

Here's one more perspective:

Some products start making money (even if not profits) from day 1. If they are able to increase customers, they are able to survive longer and if not make profits, then at least get funded. Another type (we are in to that) are the ones which know that they will start earning at a later stage (we assume that it'll be around 1.5 to 2 years), for us, survival is how deep our pockets are and how efficiently we can manage that depth. Things are super tight but there's a sense of freedom to experiment too. Getting funded is quite a task, investors (at least in India) want to see you making money/profits/wait till you go viral. Most even don't have domain knowledge of our product (surprisingly, since they've invested in a lot of EdTech ones).

We directly don't have a competitor right now whom we can mention while pitching, it's a somewhat of a disadvantage while pitching. I guess, initial funds to be raised is the point of challenge for us.

AndyDent-Touchgram · 383d ago

We directly don't have a competitor right now whom we can mention

Can you expand that? Are you saying you don't have a competitor in hosted communities or hosting software or what?

In software terms, I'd say is a hosting platform to rival what you're doing, at a quick look. So you can look for its competitors

I've seen used very successfully by Ness Labs.

As far as communities go, why can't you say Indie Hackers or various Reddit or Discord groups are competitors?

Sometimes definining a competitor is a real stretch. Touchgram's core idea and tech is so unique, I've been able to patent it. But still, with a lot of feedback (including Pioneer) I've been able to refine positioning it so I do have identified competitors - electronic greeting cards being one. In searching for competitors, you can refine how to position your product.

NFT-gal · 383d ago

Interesting. Hadn't thought about the importance of actually having direct competitors, but that makes sense. People need an actual, existing thing to relate your product to in their mind.

Also with the definition of competitors, you can position your own product's differences/advantages.

AndyDent-Touchgram · 382d ago

I also think of this more like a venn diagram overlap.

For Market A, we have these competitors.
For Market B, we have this different set.

In any one of those, "competitor" is in the startup sense of "competing way people get the job done" which is not necessarily a company or app.

Some products are so narrow they only have one market or one set of competitors.

Also, defining multiple potential markets and doing competitor analysis, or even a bit of customer development, is not (necessarily) lack of focus.

You define your alternatives so you can pick your focus.
You do the minimum amount of research/outreach to make a considered decision. · 382d ago

Exactly! We've known our market, we know what they need, we have all those features/verticals, some effect is brought in by COVID (both positive and non positive). We're just trying to find our breakthrough, it's going to be a chain reaction. If we had more money, we'd get all then needed hands. Right now there's more work (all planned and vetted) than the brains to take it up.

It's great to find an ally :)

AndyDent-Touchgram · 382d ago

Right now there's more work (all planned and vetted) than the brains to take it up

Hah - I know that feeling!

Touchgram core engine 96 issues
iMessage app 344 issues
(tiny number bugs, mostly upcoming)

That's just the tech side, without considering marketing, biz dev, admin...

Just me and the (sadly ailing) dog. · 382d ago

Take good care my friend! · 383d ago

Well this is going to be an interesting competition. Let me try to answer every point:

We don't have a 'direct' competitor. Which means, there's no one focusing on bringing all the Tech Communities together. They already exist offline (and in some parts online through multiple closed platforms), but if someone sets out on google to learn tech, communities is the last thing they would reach, or may be not at all. We're trying to bring all these passionate sharers of knowledge to coexist. (Yes, we've done our part of the survey)

There are obviously overlaps with platforms including meetup, circle,, hopin, airmeet, hubilo, slack, discord, bevy in terms of features, all of these are superb platforms. We've also heard good terms like 'unbundling of social media' for us which is applicable.

The major difference is co-existence (except with meetup) viz
- When you go to circle or any of the above, they create enclosed communities. You as a user will have to go to each community's separate website (through luckily being able to find them, or them finding you through an ad) and join them. And the same process for leaving them.
+ With Commudle, one place where you can find them all and choose what tech you want to grow in and join group/community which you think is useful for you. We're a place where you can interact with just techies and be seen by users who are part of other communities & vice versa too.

The theme for Indie Hackers is different, Reddit is very diversified in the type of content people share.

From the time I used to run Commudle as a side project to when I work on it full time now, I see the need more and more. All the knowledge being shared in these communities is amazing and yet they are not visible on the web.

The difficult part with users is when people compare us with online video hosting or chat servers (which are amazing products). Because these are just 2 features of the platform.

The difficult part with investors (in India at least) is that they still don't know of communities beyond 'campus ambassadors' and the kind of impact these communities are silently bringing in. I'm a live example and I know many more.

Too long a response, hope I could clear some doubts :)

Klog · 383d ago

Maybe totally unrelated, but what do you think about a new, closed computer. There is one social app, built in public by the public. One calendar, built in public by the public. Etc. Then you get everyone on the same platform. That'd be my (albeit radical) solution.

AndyDent-Touchgram · 382d ago

Nope, never ever going to work.

Apart from other flaws,
built in public by the public = designed by committee

Klog · 382d ago

Don't you think it could simplify things? A new device, written all in JS.

I don't agree that designed by committee is an issue. Not if there's a BDFL. What about Linux, Ubuntu, Firefox, Blender? · 382d ago

Agreed. But as @Klog mentioned, couldn't relate to it.

manojranaweera · 381d ago

Mine is just my own time, for as I am trying to build 4 businesses at the same. So our growth is slow - I have one dedicated employee. But we are growing each day somewhat at a slow speed.

As it's a two-sided marketplace, the focus is on building the supplier end, which is our volunteers. We are on target to hit 1000 volunteers by end of the first year. At this point, I plan to allocate a bit more of my time.

manojranaweera · 381d ago

The trick is to find channels that work - and then adopt techniques, which can accelerate acquisition without paying for advertising.

sole-fields · 379d ago

Why try to create 4 businesses at once? Which of them seems like it has the best shot of being successful? Why not just focus on that one, then get back to the others?

manojranaweera · 378d ago

I actually want to create 5 businesses. 5th being a sidecar fund for

Why? For me, it's dead boring to work on just one business. I'm also spreading the risk, even though the risk is very limited due to how I work and what my expectations are.

I'm on a 10 to 20 year plan. These are all the tiny pieces of that plan. As I am not looking for investment, I don't need to play the typical game that most tech companies have to play. I have freedom as much as I want.

sole-fields · 377d ago

That's an exceedingly rare quality, being able to run multiple successful businesses at once, let alone one!

How are they faring now? What if 5 years from now they all fail, but one could've been successful with more focus and dedicated energy? How do you measure success for each of them? Interested to hear what all of your businesses are!

manojranaweera · 377d ago

Who said anything about "successful"?

They are all moving in the right direction. Slow but steadily. Why should they fail? They are all inter-connected. I don't worry about success or failure. I have a destination to get to. And I am moving all of them towards that.

Here goes:

1. Trusted founder network for UK tech startups
2. Intelligence for UK Tech startups
3. Free talent for bootstrapped tech startups
4. Better investor reporting for tech startups

What's missing is the sidecar fund for (1).

4th is not originally mine. I'm the third owner. Now working with volunteers from (3) to take it to market.

Bit of fun! I treat all of them as my hobbies. I have a small team of 4 salaried employees and volunteers from (3).

sole-fields · 374d ago


davidcrombie · 382d ago

Team collaboration.

sole-fields · 382d ago

Oh this is great. How do you mean?

NFT-gal · 383d ago

For most products, the super high level will always be: win over more users. But that's a bit of a non answer.

I'm competing in the attention economy. Having done this now for several months, I've learned how expensive it is to produce content and how valuable it is to have good content. Larger companies have the means to pay. I don't. In order to win attention away from these larger companies and onto my platform (assuming total aggregate attention is fixed in the near term), I don't think I need to worry about the tech itself as much as my ability to go viral.

So for me, I supposed it'll be: can we find a way to create better content cheaply? Typically, efficiency comes from systems. So, really, it's: can we create a content system that's more efficient than our competitors?

(I don't know, is this too broad?)

AndyDent-Touchgram · 383d ago

I think you're absolutely right about the difficulty of standing out and the expense in what's a kind of zero-sum game of people's attention.
In theory, attention is a growing market with new users all the time.
In practice, I think we're already at saturation. Even if someone's a completely new smartphone user, as a child or adult acquiring for the first time, there's such a flood from the big players that it's overwhelming.

I'm in a similar situation with Touchgram with the added complication of a technically challenging product development as a solo founder (some would say ridiculously ambitious). So just getting the core of the product finished to support what I want the exterior to deliver, has been months of unexpected levels of work.

The problem with automating content creation is, unless you have something non-obvious that you keep secret, it's even easier for automated systems to be copied. We are nearly at an automated level of content creation now with blog postings - I remember when good writing alone was a way to stand out in content.

NFT-gal · 383d ago

Super interesting. Agreed on the system front. Wouldn't want to actually automate it (unless e.g. archillect [] which is a great counterexample). Just create an efficient system with a few high quality people. Some companies who seem to have created incredibly strong content/creative systems are Marvel and Pixar. Whatever structure used within their organizations to get to the final product is a real advantage.

Certainly neither Marvel/Pixar were solo ventures, so I feel your pain! Do you intend to open up the floor for other possible cofounders / employees? If not, why not?

AndyDent-Touchgram · 383d ago

I'm certainly open to the right co-founder, actually started with one who bailed early, partly because he and his wife didn't like some of the content possibilities of what consenting adults might do with Touchgram.

Employees will have to wait until we're generating signicant revenue or get investment. I've been working towards a reasonable product and traction as a journey towards that. I'm absolutely not a fan of doing everything myself. Just being across the different technical domains of Touchgram is exhausting.

Archillect looks interesting although discover and share is not quite the same as automating creation, lots easier for an AI to manage.

If you want to see a grim future for how competing automation and AI's can go, read Charles Stross's SF novel Accelerando which is now free on his site along with the back-story
summed up with one phrase what happens if this goes on?

NFT-gal · 383d ago

Oh I absolutely love this. So true about archillect. That's not creativity. Can't automate creativity (yet! ever?).

Ooo very cool read. Thank you, thank you. Cheers!