AMAs April 30, 2019

I started Drip, MicroConf and TinySeed, ask me anything!

Rob Walling @robwalling

Hey Indie Hackers!

I'm Rob Walling. I've started several companies, most notably Drip, MicroConf and TinySeed.

Along with my team, I grew Drip (a SaaS application) to 7-figures before our acquisition in 2016.

MicroConf is the most popular conference for self-funded startups, with a focus on SaaS. We've hosted it 18 times since 2011 in Las Vegas, Prague, Barcelona, Lisbon, and Croatia.

TinySeed is the first startup accelerator designed for SaaS founders who would traditionally bootstrap. We are a 1-year, remote accelerator that includes mentorship and cash investment. After receiving close to 900 applicants we are starting our first batch this month.

In my spare time I host the podcast Startups for the Rest of Us and wrote one of the most popular books about bootstrapping: Start Small, Stay Small.

I was on the Indie Hackers podcast a few episodes back where we dug into much of the above.

I'll be here answering your text questions at 10am Central Time on Wednesday the 8th of May.

Ask me anything! #ama

  1. 16

    Hey Rob,

    Long time follower of your stuff here.

    If you was starting again with no connections, followers or previous successes, how would you go about getting those first 10 customers for a new product?

    Thanks,
    Jamie

    1. 11

      I would do the same thing I did last time: look for opportunity. And hustle.

      For about 5 years I worked 40-50 hours a week at a day job, then came home and worked 10-20 hours/week on side work. Sometimes the side work was my own product. Sometimes it was consulting, and I banked all the money I made from it.

      After a few years I had enough money saved ($11k) to buy a software product that was in bad shape (alpha stage, buggy, etc). It was my first real success - the first time I had owned software that paid my house payment without being tied to hours worked.

      Some thoughts:

      1. I'm not sure I would build a new product. It's what most hackers want to do since we are makers. But I asked myself: do I want to make something, or do I want to quit my job? The pull to quit my job was stronger, thus I was willing to sacrificing some of my maker instinct and acquire a product. It got me to my goal faster. Then I had all the time I needed to work on what I wanted to work on, whether it generated revenue or not.

      2. I would not build a product and then look for 10 customers. I would find those customers first. Facebook ads. Google Ads. Conferences. Twitter. Facebook groups. Forums. It's hard work and most things you try will be a dead end. It takes more time than you want it to. But starting from scratch is the hardest stage. Make sure you only have to do it once.

      3. Communities like IndieHackers, Hacker News, Reddit Startups, MicroConf, etc. (which didn't exist when I started) are huge. Both for moral support and specific advice on questions like this (that really depend on the niche, the product you're building, etc.)

      4. Also, consider stairstepping your way up instead of trying to build a SaaS app from the start. And, at this stage consider building on someone else's platform (Shopify, Slack, Github) since they can offer built-in distribution through an app store. It's not how I would look to build a 7- or 8-figure company, but when starting out with your first app it's a way to put marketing one easy mode while you figure out all the other stuff it takes to build, launch and grow a product.

      1. 1

        Hey Rob, thanks for the detailed answer I'm sure it'll be very useful to a lot of people here on IH.

        I have actually followed your advice in the past, buying a couple of different software businesses and building them up to sell on again for a good profit. However it seems that nowadays it is much harder to find suitable businesses for sale, even with all the new marketplaces like Flippa, Empireflippers and so on.

        Do you (or anyone reading this!) have any suggestions on how to find the ideal software business for sale?

        1. 4

          Glad it worked out for you! Yes, it's become fashionable to buy.

          I would look in all those places plus FEI and Quietlight, plus do your own prospecting. The latter is where you find the best deals.

      2. 1

        I really like the last point you made here, Rob. "consider building on someone else's platform (Shopify, Slack, Github) since they can offer built-in distribution..."

        Distribution is something I've been thinking a lot about recently, and for IndieHakcers it's really important to consider when building your side project.

        Most of us have full-time gigs and don't have a ton of time for marketing and sales. Inherent distribution on "App Stores" seems like a good bet. I've recently built my first Shopify App and actually submitted for approval today :)

        1. 1

          Congrats!

    2. 3

      I have this question too, struggling to get the first 10 customers for my new product.

  2. 6

    Hey Rob,

    What is the best approach to explore and find ideas for SaaS products?

    Best,
    Cameron

    1. 6

      I covered this in-depth in Start Small, Stay Small. Some of the exact tactics and screenshots are out of date, but the general ideas hold up.

      Other thoughts:

      1. Pick a niche. Then expand.
      2. If you have an audience or reach into an audience, try to leverage that.
      3. It's ideal if it's a problem you have, but not required.
      4. I ask myself "what problems are solved today by expensive, clunky, enterprise software that small businesses won't pay for, but share that problem?"
  3. 2

    Hey there Rob,
    how much leverage do you see or feel by having multiple projects / businesses which have the same target groups?

    If you would start out new in another niche, (how) would you try to force those cross-promotion opportunities early on?

    1. 3

      One of the mistakes I made early on was owning products that targeted different groups. It didn't allow me to leverage what I had already built when launching the next one. I think the leverage is huge if you offer a series of products to the same target audience.

      General advice: you can launch a new product to an existing audience. Or an existing product to a new audience.

      But try not to launch a new product to a new audience. The risk is so high at that stage. You may have to do it once in your career. Try not to do it again after that.

  4. 2

    Glad to have you here, Rob!

    How did you enter a super competitive landscape like email marketing?

    I see that @marilynwo has already asked a similar question so feel free to skip mine :)

    1. 3

      I leveraged the unfair advantages I had built up over the prior 10 years.

      I had revenue from an existing product (HitTail, which I sold in 2015).

      I had experience building, launching and growing software products - both as a founder and a developer.

      I had an audience and a network I had cultivated since 2005 through a blog, podcast, book, conference, etc.

      I had a lot of experience hiring and managing employees, contractors, developers, and VAs.

      In other words, I followed my own advice and stairstepped my way up (https://robwalling.com/2015/03/26/the-stairstep-approach-to-bootstrapping/).

      In 2005, with no cash, network, audience or startup chops I didn't start Drip. I worked on smaller products in easier niches until I gained the experience, confidence, and cash to compete in a more competitive landscape with a more complex product.

      Similar to how baseball players play in little league, then high school, then college, then the minors, and the majors.

      It's a longer road than trying to hit a home run your first at bat, but IMO one that's much more sane and has a higher chance of success.

      To speak to Drip specifically, by building a small email-related SaaS we stumbled into a gap in the market above MailChimp and below Infusionsoft. Then we built a great product to fill the gap, and did a good job letting people know about it.

  5. 2

    Just want to say thanks for the podcast. It's a great resource for the community.

    1. 1

      You're welcome, I appreciate it!

  6. 2

    Hey Rob, if you'd face a blank page and had a limited budget, what would be your strategy to find a niche for a SaaS business?

    1. 2

      I would not build a SaaS with a blank page and limited budget. I would stairstep my way up using smaller products such that I either owned all of my time, or had budget to build something well.

      Reference: https://robwalling.com/2015/03/26/the-stairstep-approach-to-bootstrapping/

  7. 2

    Hey rob,
    congrat on all your success, you have earned. I like your effort like this to help others.
    I am working on a small idea for crypto traders like me tradeplan.io and my question to you would be.
    -what was the one piece of advice that help you stay motivated.
    -How do u validate a idea without bias.
    -How would you work around the stigma of being a non technical founder making a technology start up.
    -How important is it that the problem your solving is a personal problem the founder has faced.

    Thanks and regards.

    1. 2

      -what was the one piece of advice that help you stay motivated.

      "The harder I work, the luckier I get." I believe Thomas Jefferson said that.

      -How do u validate a idea without bias.

      Very hard to do without bias. I had conversations with 17 founders, presented the idea. 11 said "I would pay for that." We built it. It kinda worked...but I had to do some pivoting along the way.

      -How would you work around the stigma of being a non technical founder making a technology start up.

      Learn to code well enough that you can talk to developers at a somewhat technical level. I don't code these days, aside from some weekend hacking. But I can talk pretty deeply about technical challenges.

      Also, take a day job where you have to manage or work with developers. The more experience you have with them the easier it will be to hire/manage your own devs.

      -How important is it that the problem your solving is a personal problem the founder has faced.

      It definitely helps. Not required. I've done both, and I more enjoyed the products where I had the problem :-) But I would not be dogmatic about this.

      1. 1

        thanks.

  8. 2

    Longtime listener of your podcast here!

    I heard the story how Jason Roberts came up with the name for Drip and helped get the domain for you when you were on Techzing.

    What's your strategy for picking domains these days now that the number of squatters is even more than it was then?

    How much do you want a .com vs a . io, . ly, .app or something else? Would you ever have chosen a name like dev.to? Would you spend a lot to get a specific name you want? Would you start with a bad name evaluate many different options and avoid becoming attached to any until after negotiating and securing it, like Stripe did?

    And would you let Jason invest next time? 😁

    1. 2

      I pick domains that I can say out loud and don't have to spell.

      I don't mind funky extensions as long as I don't have to define the extension every time I say the domain name. "Dot kitchen. Yeah, it's weird, but dot kitchen is now a TLD."

      I would consider starting with a bad name and switching later. I've done this.

      I am now trying to stay away from the prefix/suffix names, and would probably go with a .co, .ly, .app, etc. before adding "get" or "meet" or "app" to the end of the product name.

      I got very tired of people calling Drip "GetDrip" because the domain name was "GetDrip.com." I wish I had purchased drip.co or drip.ly, but they were a few thousand dollars when we were starting out and I needed those funds to build the product. I should have switched to one of those within the first year, once we were successful.

      1. 1

        Thanks, I'd never thought about people mistaking the prefix for part of the name.

        Looking forward to the next Startups for the Rest of Us / Techzing crossover episode!

  9. 1

    Hi @robwalling,
    I really enjoy reading your answers, thanks for that!
    While reading some of your articles, I've noticed that some redirection links are not working, like this one: http://webcontrolroom.com/the-simple-guide-to-content-driven-seo/, in the article called "Case Study: 13 Pre-Launch Traffic Strategies for Startups (Part 1 of 3)"
    Same for the redirection of http://www.inform.ly/, not working as well.
    Hope it helps

    1. 2

      Yes, both of those are defunct startups. So the redirection is working, there's just nothing on the other end ;-)

      1. 1

        Ok thanks :)

  10. 1

    No question. Just wanted to say Tinyseed is a fantastic idea and I was one of your 900 applicants. Following it closely!

    1. 2

      Thank you!

  11. 1

    Hi Rob,
    All of this is so new to me I would like to know what do I need to do to get funding for a business I want to start. Please let me know as I am ready to get busy. Thanks a million!

    1. 3

      I don't believe founders should ask for permission (i.e. funding) to build a business. Build it without funding. This is what I did for every one of my companies.

      There is a time and place to raise funding, and it's once you have some traction. Once you are pretty confident the idea will work. So consider cobbling an MVP together using Zapier and duct tape. Or manually handling a process that software will handle in the end.

      Until you have some people paying you (or begging to pay you) for solving their problem, you don't really have a business. And investors want to fund businesses, not ideas.

  12. 1

    My good Rob,

    Kind of like the famous "typography class" that fueled Steve Job's love for type, and pleasant visuals, and stuff...

    What are some key elements in your personal history/background, which helped you in your entrepreneurship life, and then poured into your companies?

    1. 3
      1. I grew up in a working class family. We always had enough to eat, but if I wanted new headphones, batteries for my Walkman or a new comic book I had to make money. This desire to make money led me to start selling candy and comic books at a markup, igniting my passion for running my own business.

      2. My parents bought me and my brother an Apple IIe when I was 8 years old. Games were $50 (about $130 in today's dollars). So we learned to build our own. This is why I learned to code, and the power of being able to make something out of nothing was nothing short of magical for this 8-year old.

      3. I ran track for 9 years in high school and college. I learned to set goals and work very hard for months before seeing results. I watched as teammates quit the team because it was a long road. This taught me that just showing up every day and putting in the work is something most people are not willing to do. Thus those who do it have a huge advantage in life and business.

      1. 1

        Thank you so much for your insights. Just the kind of answer I hoped for!

  13. 1

    Hey Robs,

    Thanks for taking the time to answer questions from the community.

    What are your views on building B2B SAAS products on top of other company's platforms?

    The examples that spring to mind are Hootsuite on top of Twitter and Jungle Scout on top of Amazon.

    1. 3

      This comes with platform risk, but also offers built in distribution.

      I'd say it's a great way to build a nice six-figure business. But risky if you want to build a large company, as you will have more risk the larger you get, as you find yourself on the radar of your platform.

      Personally, if I were starting out I would consider building on a platform if I thought their app store could provide distribution. But I'd be counting the days until they put me out of business, so would be looking for an exit sooner than if I had built something on its own.

  14. 1

    Hi Rob

    Looking forward to hearing your responses to all these great questions.

    I was wondering if you could talk a bit about the TinySeed evaluation process and if there will be feedback for those that are not successful this round.

    Thanks
    Kerrin

    1. 2

      We received close to 900 applicants, so we aren't able to provide feedback on individual submissions. The first pass of the process began with asking if the submissions was within our thesis of B2B SaaS.

      Then we looked at metrics. And another pass looked at the team, whether they had product/market fit, their pricing/ARPU, and then the product itself.

  15. 1

    Rob,

    Thanks for your many contributions to the community.

    Now that you've grown successful businesses and seen hundreds of Tinyseed applications, if you had to pick one quality of a solopreneur that gives you confidence s/he would succeed, what would that quality or trait be?

    1. 2

      I don't believe there is a single trait. I don't even believe there's an archetype of a person who will be a successful solopreneur. I do think there are assets that will increase your chance of success. Such as:

      • Creative problem solving
      • Ability to focus on a goal for longer than most people, without much reward in the short-term
      • An intense desire to make something work
      • An audience or healthy network
      • Ability to connect with people
  16. 1

    Huge fan Rob! Thanks for jumping in to do this AMA

    Question, how do you estimate what role luck had in your successes?

    1. 5

      I have been very lucky. I was born in the U.S. to two parents who stayed married and sent me to school everyday. I always had enough to eat. I was exposed to a computer at age 8. Neither of my parents graduated from college, but the expectation my entire childhood is that I would.

      On the flip side, I was public school educated from Kindergarten through college. People in my family have been addicted to alcoholic and/or drugs. My dad had OCD so bad he didn't leave his bedroom my senior year of high school.

      So it's been a mix. For me, I believe the difference was the hours sitting in my car writing code on my side project while co-workers went to lunch. Or writing marketing copy from 8pm-2am, then getting up at 8am to work the day job. Those were the things I did that my peers weren't doing.

      I believe they made a bigger difference than luck. But one can never know for sure.

      "The harder I work, the luckier I get." - paraphrased from Thomas Jefferson

      1. 1

        great reply thanks!

  17. 1

    Hi Rob. Congrats on being a serial entrepreneur.
    I am B2C SaaS founder right now, looking to go consumer. Is that a good strategy if you have over 25K users across different businesses? What would you suggest?

    1. 2

      B2C is totally doable. Just know that vs. B2B your customers will tend to be more price sensitive, have higher churn rates, be less tech savvy, and require more support (and often want phone support vs. email or chat). Those are the major trade-offs you'll be making.

  18. 1

    Where/how do you do business development? (i.e. getting the word out and getting early adopters)

  19. 1

    I recently read through Start Small, Stay Small. It mostly holds up, but the SEO advice feels a bit out of date. Do you have favorite tips/resources for SEO in 2019?

    1. 3

      Yeah, SEO changes so quickly. I think the SEO advice I gave there was out of date within 18 months of publication.

      I like the material AHrefs.com puts out. Rand Fishkin, as well, through his new startup SparkToro.

  20. 1

    Hey Rob, thank you for your time :) My question for you with respect to Drip is:
    What do you do to earn your first 1000 true fans in an environment with other similar products like ConvertKit, MailChimp, Infusionsoft, Active Campaign, Ontraport, etc...?

    I'm sure you get a lot of people asking you what's the difference between Drip and the other email marketing tools. Hope to hear from you on your ways to stand out and gain the trust of your followers.

    Appreciate your help :)
    Marilyn

  21. 1

    How did you validate? And where did validation occur in your product development life cycle?

    1. 2

      I validated Drip before we wrote a line of code. I had conversations with 17 founders, presented the idea. 11 said "I would pay for that." We built it. It kinda worked...but had to do some pivoting along the way.

  22. 1

    @robwalling Hi Rob,
    I'm starting out and I'm building a b2b sass product for local independent businesses. I know SEO would take 6-8 months to rank my website and im wondering if facebook/google ads are a good way to bring in business. Im getting someone to build a clickfunnels sales funnel so i can send leads to this funnel. Is this the best way to do this for a SASS B2b business if i have 0 customers and only starting out?
    Btw i do have a reasonable budget to spend but im wondering if spending it on ads is alot of risk?

    1. 2

      Ads can work. I'd test it.

      Also, waiting for SEO is a bummer. Since you have budget, consider acquiring a site that already ranks for your terms and re-purposing it.

  23. 1

    Hey Rob, a big fan here. I have always enjoyed listening to you and Derrick from other podcasts. I am currently building https://letterfromyou.com/ on the side. It's been fun working with family members to offer this service to people. I am having hard time with pricing—everyone advices me to charge more but I am trying to justify the price that is beneficial for both ends... (this is my first side project, so it's hard to gauge) I am creating a business tier for the product where I offer Zapier integrations and such... If you were to advice me on pricing (as if I am in your TinySeed accelerator), what price range would you suggest on the business tier plan for this kind of product? I would love to hear your thought process on how you price things.

    1. 3

      I would have a lot of conversations with potential customers, and split test pricing in those conversations. I like building products that start at $49/mo (and up - $99 is even better), so I would aspire to build something that is worth that much to people.

      I call this aspirational pricing. Not setting the price based on what you've built, but building something to provide enough value that you can hit a target price point.