May 10, 2019

Office Hours with Rob Walling of Drip, MicroConf and TinySeed

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 holding an #office-hours session on Wednesday 22nd of May at 11:00 Central Time and I'd love to talk to you.

Share your challenges and I'll pick 6 of you from the comments to email the details on how to attend.

  1. 1

    Hey Rob,

    My wife and I started a hobby project beginning of this year called It is a service that enables business owners to connect with their clients through beautifully handwritten letters. We created an API as well, so businesses can automate the process through services like Zapier and other SaaS applications (even Drip!).

    I am now starting to do some outreach to companies who might want to utilize the service. I am trying to reach out to mid to enterprise level companies. My initial thought is to reach out to marketing people of the organization. I would love to hear your advice if there is something I can offer more that might entice them to try the product!

  2. 1

    Hi Rob,

    Big fan of your teachings. In March of this year, I quit my job to work full-time on

    Flowboard is an artist management application which helps model/talent agencies to run more efficiently & become productive.

    Currently, There are a bunch of features which helps them to stay on track:

    • Artist Calendar
    • Client Management
    • Artist-Client Booking (appointment) management
    • Account & Invoice management
    • Powerful reporting

    At the moment, I have 3 medium & enterprise organisation as a customer. I'm working towards growing in terms of customers this year. Right now I'm doing ~1k MRR with the product.

    I would like to discuss how to go about selling this product to enterprises & reaching out to global audiences.

    P.S: I was selected for a scholarship in MicroConf 2019. But, I couldn't make it, unfortunately.

  3. 1

    I've love to RSSVP for office hours. I am founder of https://epic.Ai We're in early growth stage. Between the suite of products we've created we're $60k MR on our non recurring products and $4k MRR on our subscription products (growing ~45-60% MoM). Our burn is $80k so we're struggling to find a bridge to accelerate our growth. We don't want to take on funding, instead we want to become resourceful and find a way to tackle growth. It would be an honor to do office hours with you and pick your brain and see if perhaps you can provide a better lens or a new perspective on our current state. Thanks again!

  4. 1

    Hey Rob,

    Love the stair step approach concept.

    My starter question:

    When is an idea validated or a good rule of thumb to go free validating an idea to building an idea out? 10 potential customers say "that's cool I'd give you $X"?

  5. 1

    Hi Rob,

    I am building a money management tool for small business called cashflowy. I built is as a scratch my own itch solution. Here is a quick demo of the same -

    I am at the stage where I have dog-fooded the solution for 6 months. I know for sure it works for me. My objective from a marketing perspective is to find people like me. The product is currently in POC stage but I use it every day. The product is missing polish and perfection.

    I want to bootstrap the solution and I would like to know how I should be spending my resources (time and money(my personal software consulting business is doing well)) to get the product some polish so that I can convert people into paying users.

    Btw, I have some pre-sales. Struggling to get beyond pre-sales.

  6. 1

    Building a debugging as a service productized service. The key issue I've been dealing with is letting prospects I can help them, when they urgently need me. All work had so far has been by referral.

  7. 1

    Hi Rob!

    Thank you for taking the time to help fellow IndieHackers! I have two fundamental issues that I'm trying to solve:

    1. Time to build product/Quality of product — my product becomes better the more content customers put in. So, I require commitment from as many people in the customer's team as possible. So, for me to earn the trust, I need to build a quality product, which requires time (even after cutting everything to a bare minimum), which is problematic to find with a day job. The obvious solution is to try to get funding, but that leads to problem number 2.
    2. Lack of connections — I moved to the US only a couple of years ago and don't know many people around, even less in investor/angel investor world. Having only customer interviews and "landing page + ads validation" with no real customers and months away from beta-version and no history of success makes raising funds hard for me. A couple of investors I talked to (from my point of view) were nice to me, but have no intention to be involved.

    My plan is to prioritize the quality of the product and rather stay small, but I'm afraid that I won't be able to take this thing off the ground with my current schedule/commitments.


  8. 1

    Hey Rob!

    I have been building my bootstrapped SaaS business over the past couple years, things have been going well so I am finally no longer eating Ramen every night for dinner! The SaaS is B2B (SME), in the sport registration space (online event registrations and payments). The business is in low four figures MRR and with the growth comes a lot of new challenges I haven't faced before that I would love some insight on. I list two topics, but have a preference to discuss the first topic, the second is a backup.

    1. (HIRING) I am a solo founder, so I have to wear all the hats and do a bit of everything. I am starting to realize that when I am doing certain tasks, especially UI/UX design, I take A LOT longer to complete things. So this seems like a natural first area to hire/contract help, but having never used professional freelancers, just small fiverr jobs, and not coming from a traditional technical environment, I am unsure of the best ways to find and work with designers effectively. Could you provide some insight into how you found and managed your first employees or contractors for the early days in your startups? Or what you have learned to be good strategies to find and work with the first hires/contractors.
      As this feels like a scary/risky time to hire when revenues are still low, but I know this is a bottleneck I need to fix so I want to get this right.

    2. (TECH STACK DECISIONS) My SaaS application is completely built on, which is a fairly robust no code platform. This has enabled me as an originally non-technical founder to fully build the software and make very fast updates when needed. However, two downsides are that there is a lack of Bubble experienced talent to hire and I also fear that the business will not be an attractive acquisition target because it is built on another small proprietary platform (an acquisition is a possible goal for the business, but mostly I want to keep my options open). So I am curious if you have any insight into re-building a SaaS platform in a new tech stack and ways to properly weigh the pros and cons of this to know if it's a good move for my business?


  9. 1

    Hi Rob,

    Love the content. Also, bronze and modern age comic collector(trying to finish up My TMNT volume 1 collection in the next year or so.)

    My project:
    The problem - Solving the problem of too much Marketing and sales content and questions and not enough action or lack of how to implement.

    The product - SaaS product that incorporates a hyper-collaboartive eco-system with marketing/sales tools and a marketing/sales community in one place for indiehackers/makers and early stage start-ups. SaaS with Network Effects.

    My questions:

    1.) I have a strategy where im going to just sort of brute force my marketing and sales and try to get the engine sparked in terms of feedback, starting conversations, lead generation etc.(Social Media, Cold Calling , Cold Emailing, Cold Messaging etc.) Is this the best way to do this or should I carve out a focused plan where i test out what channels work best for me then hit those the hardest? Best practices?

    2.) I cant seem to pinpoint what metrics are the most important for something like my product since im catering to two targets. I want to just keep it simple and say that user growth monthly and user rentention monthly would be best but I would love your input on this for businesses in the Verison 1 build and testing stage.


  10. 1

    I was on a previous Office hours with @csallen and that was an amazing experience, if you don't have the numbers I would love to be in it :)

    I have been listening to Rob for over 4 years now. His podcast Startups for the Rest of Us was one of the main reasons I got on this path (Bootstrapping).

    Before that I was looking at VC funded startups which didn't make much sense to me at that time. The podcast showed an alternative that most blogs/podcasts never talked about.

    If I get picked I will have two questions I believe Rob has unique insights into

    • How to market a new SaaS product in a competitive market? (Drip vs Mailchimp) (Versoly vs Templates/Wordpress/Carrd/Squarespace)
    • Building an email list in such an environment where great content is being produced constantly, while being time constraint due to working on development, marketing and sales.
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