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Lessons we learned while bootstrapping

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Re: Lessons we learned while bootstrapping

#31
post #14

Earlier quoted context omitted.

It's hard to give advice without knowing more details, but this sounds like there is really no need for what you're offering. How did you come up with the idea? How do you know it's something people want in the first place? To me, this sounds more like a fundamental product problem as opposed to a sales/marketing problem. Try talking to (potential) users and find out what version of the general idea you want to build…

I ran into this problem with my previous startup. We had cool tech, but it didn't solve something that was a major active problem for them. OP - you may want to examine if you're offering a solution in search of a problem. Problems are harder to find and drill into than solutions. (And enterprise sales are hard, so make sure you're aware of the software valley of death and are in the mid 5 figure annual contract if y…

> are in the mid 5 figure annual contract if you've got a long sales cycle

our initial price was there but we've scaled it down exactly because of the long sales cycle (which honestly i could tolerate if i knew that i was actually in a cycle rather than circling the drain).

Re: Lessons we learned while bootstrapping

#32
this blog post is a kind of guide to starting your own company and making millions of dollars. this is a little unrelated but i just find it funny to read this guide because its very convoluted. there is actually a much simpler guide that their guide is a derivation of. here is the actual guide:

step one: be more intelligent than most people

behind almost every business, behind almost every professional success and behind almost any success in general that ive seen, is a highly intelligent person. i find it irritating to read because the concept of a guide is spelling things out so that anyone can follow the steps and get the same result. successful people always benefit from high intelligence, money and success will always be unfairly skewed to the benefit of those who happened to be born with better brains and into better developmental circumstances. nobody needs this guide because they are either smart and dont need a guide or dumb and in which case cant use this guide.

Re: Lessons we learned while bootstrapping

#33

here's my problem if anyone is willing to lend a helping hand: i'm building an enterprise saas product that involves some cool buzzwords and potentially really adds value in the space i'm targeting but i'm getting no traction. i have an mvp (phone app and webapp) to demo to customers. i have the decks and sales pitch. i'm a reasonably smart and articulate person and communicate well (able to "speak sales"). yet becau…

My advice: take a sales class. I waited waaaaaay to long to do that and realized so many mistakes and missed opportunities in hindsight.

Are there any good online sales classes?

Re: Lessons we learned while bootstrapping

#34
post #13

I've been bootstrapping https://www.castingcall.club for about 2 years now. Although I don't have a team (just me) and I've not in the 7-figure range (still in 6), a lot of the lessons from Kinsta holds true. I wanted to point out one bullet though: Automation My product is a SaaS product. I've automated every single thing possible from self-creating wikis to recommendations. I stepped away to visit Japan for 3 weeks…

Agreed with the automation — I’m a fellow bootstrapper[0] in the SaaS space, and wouldn’t be without it. If there is anything that can be automated, even if slightly prematurely before the need to scale arises, I do so. In terms of infrastructure, this meant using Ansible for quickly deploying new servers where needed and adding them to the right load balancer. Currently all I need to do is spin up a new instance wit…

Also have a young family. Having a semi-passive source of income is a massive sigh of relief on family life. Been married for 10 years and my wife has never been happier.

+1 on slight premature automation. In my case, there are 70k signed up users, so doing anything manually at this point is out of control.

Re: Lessons we learned while bootstrapping

#35
post #9

Is it possible to block all websites from asking about enabling notifications? Every time I have allowed it have I regretted it, and every time I see the little dialog box asking for my permission do I feel slightly more desire to just close down the tab and read something else.

In firefox, change the dom.webnotifications.enabled config to false. Type about:config in the address bar, accept the warning, search for the key and toggle it.

Re: Lessons we learned while bootstrapping

#36

here's my problem if anyone is willing to lend a helping hand: i'm building an enterprise saas product that involves some cool buzzwords and potentially really adds value in the space i'm targeting but i'm getting no traction. i have an mvp (phone app and webapp) to demo to customers. i have the decks and sales pitch. i'm a reasonably smart and articulate person and communicate well (able to "speak sales"). yet becau…

Are you running free trials? Giving potential customers an adequate period of time to evaluate your product can be a good way to get them past some of those early hang-ups, especially if you're there to hold their hand.

Edit: I see in your other comment that it's related to lead gen at trade shows, so see if you can convince customers to use a free trial at a trade show so they can actually see the value (and have invested in the platform with real leads by the time you come knocking with a bill).

Re: Lessons we learned while bootstrapping

#37

here's my problem if anyone is willing to lend a helping hand: i'm building an enterprise saas product that involves some cool buzzwords and potentially really adds value in the space i'm targeting but i'm getting no traction. i have an mvp (phone app and webapp) to demo to customers. i have the decks and sales pitch. i'm a reasonably smart and articulate person and communicate well (able to "speak sales"). yet becau…

It's a networking and numbers game.

Did you guys pick this product out of the blue, or do you have industry experience? If you have industry experience, reach out to your network. Both for trying to get actual leads and for simply soliciting their feedback, even if they won't be a customer themselves. The feedback in and of itself will be valuable, and after you've exposed it to them, they may know of someone to connect you with, and eventually you'll land on someone that's willing to bite.

> i have no company history, no clients, no credibility - in a word no social proof - for the life of me i can't get any traction. The above piggybacks off your past experiences and working experience to try to force some initial social proof. If you can't do that, it does get harder and is more of a raw numbers game to try to have conversations with as many people as possible.

> i've had probably 10-15 sales conversations in the last 4 months that have gone absolutely no where That's less than one a week. Your number should at least be an order of magnitude higher than that. Especially with Enterprise clients, the deal rate is going to be really low and you counter that by a high volume of outreach. Even if it's just cold contacting, rather than leads from investors, you should be reaching out to several people per day, and following up with a regular cadence (which can be automated). Rarely do you hear back on first contact, and multiple touch points, which works even if it sounds skeezy to non-sales people (including me, I work for a demand/lead generation firm and know sales pipeline figures from an analytics perspective, but hate doing sales myself). Or even just one new person a day. But definitely not one person a week.

> an enterprise saas product that involves some cool buzzwords and potentially really adds value in the space i'm targeting but i'm getting no traction. Is the added value worth the headache of integrating your tool? Is your product replacing an industry-standard in the space or augmenting it? Introducing change is hard and every change introduced simultaneously introduces a level of operational risk (from the change management process itself to the added dependency of your product in their work chain). Most organizations resist change, and your product either has to be seamless enough to be perceived as low friction to introduce or have a large enough upside to be worth the hassle/headache of introducing it.

> (able to "speak sales") In enterprise sales, you need to speak sales and dance politics. Depending on the level of decision maker you're targeting, they'll have different levers they can pull, different politics they have to play, and different constraints on what they can do. Your pitch needs to account for the concerns of the decision maker you're speaking to. A middle manager will have different concerns than a division director than a C-level individual. You also need to make sure the person you're speaking with can actually make a decision related to your. Are you BANT qualifying them[1]?

> one customer says price is too high, another doesn't even mention it. Different customers will value your product's impact differently. You'll always get conflicting responses like this, and until you have a higher volume of responses you can't make much sense of this. But one thing to keep in mind is what I mentioned above - different level of decision makers will have different responses. A middle manager may have authority, but they're working off of a "what can I put on my procurement card" budget because they know your project will die if you have to actually get approved as a vendor and get billing set up with accounts payable. So your product can be perceived as too expensive, when it's really just too expensive for this individual to push through on their own. Don't take this response at face value, dig into the reasoning behind it. Creative payment terms can sometimes solve this. Other leads may know they have full authority to sign an annual contract and pay up front, and won't mention budget being an issue. Normalize your contradictory signals by the situation of the individual giving them, to get a better idea of what your target demographic is and what your true issues are.

Also, in the case where the customer says the price is too high, if that's their only hangup, discount the price significantly (or stretch an annual term into an 18 month term at the same rate, so they get a cheaper per-month rate but you lock them in for longer but renew at 12 months and the discount disappears without explicitly changing your rate on the client). Make sure you include language related to permission for a case study and testimonial as part of the discount terms. Chalk it up as a marketing expense to gain that first bit of social proof, and leverage it for other pitches.

[1] BANT - Budget, Authority, Need, and Timeline. A crude but effective sales qualification process which validates a lead is worth continuing with, and also helps you identify which points you need to work focus on. For example, if you qualify the person has a budget, need, and timeline, but no authority, you know the company is a potential client but need to figure out how to get a more authoritative person involved in the discussion. If it's timeline, then follow up later on. If it's Need, then convince them of their need (or give up). Etc

Re: Lessons we learned while bootstrapping

#38

this blog post is a kind of guide to starting your own company and making millions of dollars. this is a little unrelated but i just find it funny to read this guide because its very convoluted. there is actually a much simpler guide that their guide is a derivation of. here is the actual guide: step one: be more intelligent than most people behind almost every business, behind almost every professional success and b…

Sure, if you look at it from the closed mindset that nobody improves or can "git gud".

It's been proven time and time again that humans can learn and adapt to achieve their own aspirations. Take one quick look at the special olympics; you'll see a very large group of individuals who have all overcome amazing obstacles to become olympians.

Similarly, highly intelligent people may not have the domain knowledge required to understand how to bootstrap a company. Their knowledge domain may come from a completely different environment or culture which has its own mindset on how to bootstrap a company. Being smart does not necessarily make you more equipped than "dumb" (and highly motivated) people, but it does give you a decent head start.

Re: Lessons we learned while bootstrapping

#39
I admire them - they use 20+ SaaS products, and most of them are extremely useful for automation leading to saving tons of time and effort. Unfortunately, they're quite expensive for people just starting out with zero funding.

Re: Lessons we learned while bootstrapping

#40
The #1 best piece of advice in the article is:

> The best way to get things done is to simply sit down and start working on them.

So many people worry so much about failure that they don't even bother to start. You can't possibly plan for every roadblock and eventuality. The only thing you can control is your execution, and there are no short cuts. Hard work won't guarantee success, but lack of it will guarantee failure.

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