Breaking Into Bootstrapping Your Own SaaS Business with Clifford Oravec of Tamboo

Episode #009

Thinking about becoming an indie hacker? Learn how to start, what skills you need, and the biggest pitfalls to avoid in this discussion I had with Clifford Oravec, author of The Epic Guide to Bootstrapping a SaaS Startup.

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    My main takeaways:

    • Did consulting for a while, and was getting paid top dollar for his time

    • Most SaaS's don't fail because of lack of technical skills, its usually because of lack of a solid business model / marketing or sales skills

    • Start small by learning to sell real products, just to get that knowledge and experience

    • The best way to come up with a good idea is to start a business, and come up with all the things that would make you more money, then create a service for other businesses

    • It's going to be slow. At first, you have to be very involved in the customer acquistion process of finding customers manually, talking to them 1 to 1, sending 100s of cold emails every month

    • Don't get tricked by the fancy marketing and sales techniques that established businesses use while up and running, because at the start there is a lot of manual, definately-not-fancy grunt work that you have to slog through for a long time until you get the ball rolling

    • Most people don't even talk about the hard early stage, but it's THIS stage that is make or break

    • You need to go through that product/market fit "song and dance" we all have to go through

    • It usually takes about 2-3 years to get to a good MRR, expect 0 for quite some time

    • If you can't sell your SaaS one on one, you most likely will not be able to market it

    • Sales is EASIER than marketing! Start there!

    • The skills you're going to need to know are more business skills, than technical

    • If your idea already appears in Google, it doesn't matter, INSTEAD - ask people who you think need this solution, and if they DON'T mention the brand you found in the Google search, THEN you know that the opportunity is still may be open for you to execute on

    • Don't sell, help people buy

    • Always appear to the customers desires

    • Make them money, Save them money, Save them time

    • Don't overanalyse before you go out there. Don't waste time reading books that solve future problems, the books out there are mostly for sillicon valley style startups who are at a stage way beyond yours. Only read books that solve a problem you are having RIGHT NOW

    • Focus on the next stage in front of you

    • Learning is like seesaw-ing, you read then apply, then read, then apply, then read and apply

    • Figure out WHY exactly it didnt work

    • Build an MVP, dont spend 6 months building something, spend max 3 weeks on a prototype and validate it

    • Be radically transparent of everything you're working on

    • When you take actions on a regular basis, pushing things out week after week, you're getting constant feedback

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    Ask away! I'm lurking 😜

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    Excellent interview, Clifford! I'll be launching my landing page very soon (should've finished it some time ago, but life got in the way), and will be using the advice in this podcast to help better the messaging of my content (I found that I wasn't relating to them well enough)! Thank you as always, Courtland, for such great interviews and podcasts!

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      You should share a "before" and "after" here so that others can pick up on some of the nuances behind the changes you made.

      This is probably one of the biggest hurdles facing most of us - realizing that people don't care about us or our products - they only care about themselves and what you can do for them.

      I think it would be valuable to show how your message evolved to be more on point for your customers from where it was. Examples like this are useful tools for learning.

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        I will absolutely do this! It's been quite the learning process for me, so I hope it will be helpful for others. Thanks!

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    Clifford, thanks so much for the interview and the epic guide - I'm a huge fan of the work you've produced and really appreciate you making it available for us beginners. :)

    The two things I really loved from this interview were 1) the analogy of indie hacking being like dating and the sense that you're not committing to your product on the first date, and 2) the point you made about the psychological differences of being bad at something privately while coding, versus doing it publicly with marketing. I think both of these will stick with me and hopefully help motivate me through the times where I'm feeling lost or frustrated.

    If you have time or interest, I'd be interested to hear more about your early marketing failures, what you learned from them, and how you persevered through it without giving up and ended up with the epic guide. Did you have an audience before that or did it just take off out of nowhere?

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      Trust me when I say that I'm absolutely embarrassed by my early marketing attempts. (Truth be told, I'm still embarrassed by some of my marketing attempts but I don't let it get to me anymore. Live. Learn. Repeat.)

      Like a lot of you here, I was a total n00b (yes, with the zeros). Except when I was going through it, I didn't have an awesome place like IndieHackers to learn the ropes from 😉

      There are three big things I learned from my early marketing failures.

      1. Sell before you market. If you try to market without first knowing why people buy from you, you're just spinning your wheels. Do some sales first. Yes, it's uncomfortable. But so is spending countless hours (and dollars) doing marketing with no results. Learning why people want what you have to offer through sales helps you to scale through marketing. Seriously. Do this.

      2. Don't think that other people's marketing is working. You'll see other startups doing some marketing and you'll think you should do what they're doing. Don't. A lot of people are throwing shit against the wall (aka "marketing") to see if it will stick. If you copy their shit, you'll have shit of your own. Pay attention for new techniques, but don't think that it's working for them. Always approach things with a rational mind.

      3. It's never about you - it's always about them. This took me forever to learn. Learning how to communicate in benefits instead of just features. But this is absolutely key. When you are marketing, it is not about you. No one cares about you or your product. They care about themselves. So your marketing better be about them and what they want. Otherwise you're just doing that "look at me" marketing that we all know and hate. That shit doesn't work. You might create a "brand" but it doesn't mean anyone's going to buy from you. Make it about them.

      How did I persevere?

      Tenacity. Willpower. Stubbornness. Belief. Desperation.

      If I were smarter, I'd probably have quit.

      But I swore a holy oath that I would make this work. You can't just bail on holy oaths like that, right?

      So I stuck at it even when it was obvious that I sucked.

      Because I knew that the minute that I gave up - that was the minute that I absolutely failed.

      Now, I felt like quite the failure while all of this was going on, so I'm not saying it was much better in any way, but that's how I did it.

      I just expected that I would and wouldn't take any other outcome, regardless of how appealing it looked at times.

      It also helped to remind myself that if I stopped, then all the years I had spent were ultimately wasted. So I had to figure this out, or I had wasted my life. (Yes, I get deep like that.)

      As for The Epic Guide?

      Pure. Fucking. Luck.

      I wrote about about that here: https://medium.com/@cliffordoravec/the-morning-after-startup-famous-for-24-hours-dab9d6b2c036

      But basically here's how it went:

      Prior to The Epic Guide, I had been building SaaS applications for small non-sexy niches that don't get startup accolades. I put out The Epic Guide after I felt I had "cracked the nut" in a repeatable way to help bootstrappers like me. At first, it didn't really take off. Then it did - but not by my hand. Read the link above for the full skinny :)

      But it's like a bunch of virgins sitting around talking about... intimacy let's say. I used to be "one of you", but somehow I got lucky. (Yes, awful pun I know.) But my point being: I got "lucky" and so can you! Just stop worrying about it and start doing things.

      Best of "luck" 😜

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        "Epic" response Clifford - thanks so much for the thoughts and really appreciate you taking the time to write them down. I hadn't seen that write up before and it was exactly what I was interested in.

        I just preordered your book - mostly just because I've easily gotten $25 of value from your blogs and wanted to support you. :)

        Keep up the awesome stuff!

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          🙏 👊

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    Clifford, that was an awesome podcast interview.

    What is your best sales or marketing tip that you picked up while in the trenches, that has helped you the most?

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      It depends. 😜

      If you're pre-idea stage, this is a huge tip you should take note of: Pick a market and idea that:

      1. You'll enjoy selling and marketing to.
      2. You know you're able to sell and market to.

      Too many people start a project with no idea how they'll find customers. Avoid that if possible. Accept the reality that you're going to have to sell and market this thing. Make sure you're prepared for what that will take. People don't "just show up".

      If you're post-idea stage, there are a few tips.

      The first one is, realize that channels dry up. You might have a channel that works perfectly fine for a while, but then it will start to diminish. Always be looking for new channels.

      The second one is, get good at psychology. Understand what it's like to be your customer if they're going through your funnel. Let's say that they found a content marketing piece of yours and come to your site. Your only option is "Sign Up Today!". That prospect might not be ready to sign up today. You need to have another option for people that come to your site and are looking for more information or are looking to compare solutions. You need to come up with ways to offer those things, otherwise you've just lost what could be a perfectly good prospect.

      The third one is, create lead generation tools. This goes off of #2. Most people are not ready to buy the first time they come to your site. You need to offer things they feel they'll get value and benefit from in exchange for an email address or something similar. These are called "leads". You need to qualify and nurture your leads. You'll get more customers this way. Trust me. Don't leave leads on the table.

      The fourth one is, sales trumps marketing when it comes to immediate results. Especially in the early stages. If you want money as close to right now as possible - spend more time selling instead of just marketing. Marketing is something that takes time to start to work and pay off. Also, your marketing gets better the better that you understand your customers and why they buy. Doing sales will help you not only make more money up front, but also help your marketing game.

      Where are you at in your startup journey? Maybe I could throw a tip out here for you that would be more on point for where you're at right now?

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        Clifford, thanks for taking the time to write a detailed response.

        Right now I am reworking my initial version based on customer feedback. I try to talk to potential customers when ever I get a chance. I know face to face does not scale well, but I feel I get better quality data being able to hear voice tone and see body language.

        I am really just at the very beginning on my journey.

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          This is good!

          Do things that don't scale until you get to a point where you start to get diminishing returns.

          As developers, we often want to scale out the gate.


          Do things manually.

          When you start to feel you aren't getting the benefit you once did (you'll know when), then change things up.

          Keep up the good work! It's a slog, but it pays off. You're on the right track. 👊

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            thank you for the words of encouragement. It is really great to have a people like you in the IH community.