$26K MRR app product roadmap diary

Your product roadmap might suck

Whether you’re just in the planning phase or you’re like us… in the black, with a decent monthly recurring revenue…you’re going to need a product roadmap.

And that product roadmap is going to change often depending on a number of factors.

But what does it really mean to sit down and create one?  Or to collaborate on one with your team?

In this unique article, we bring you inside a bootstrapped SaaS strategy meeting and show you exactly how we plan out our product roadmap and give you all the juicy insights you need to be successful when your ready to build yours.

Day 1: Arrive in San Francisco 

Now Jeff and I could have done this via Skype but we both weren’t too terribly excited about sitting at a computer for 8 hours as we discussed crucial elements of our baby.

So we decided that I would fly up to San Francisco to get some meaningful face time as we plotted to take over the world.

Jeff had recently quit his engineering job at Uber and I had some vacation time so we set the time and booked the date.

If you can avoid San Francisco, I would.  It’s terribly expensive and immediatly after we booked everything and realized how much we had spent for lodging, travel, etc. we decided to have Jeff fly down to Los Angeles in the future.

Possibly even meet in Denver or Las Vegas.  Anywhere except San Francisco.

After all, we are a bootstrapped company with no VC money whatsoever.

The digs and other semi important stuff

The weekend that I flew up happened to be a bad weekend as well.  There was some sort of big conference going on followed by a Google conference the next weekend as well. 🤷🏻‍♂️ FML!

Every hotel was bursting at the seems.  And their prices reflected it.product roadmap

I managed to get a half way decent priced hotel for SF standards, I was later told.

I ended up at the Standford Court Hotel in the Nob Hill area of downtown and it seemed just fine to me.

The room was in the $350ish range I think, so for four nights we were already in the $1,600+ area in spend.

We invited our only angle investor up to join us so we felt like we needed a co-op meeting space too while we were here.

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The reason I mention all this is because it’s the behind the scenes sort of stuff I would like to know if I were following along as a reader, but also, we wanted you to know the real numbers.

Bootstrapping is about discipline and being smart with your money.

This was a big spend for us and we would have loved to have spent it on some code development instead but we were iterating on our software in a big way for our 2.0 launch.

product roadmap

Wrote this article here.

We had a product roadmap to make.  This shit was important.

The flight from Los Angeles to San Francisco was $156 roundtrip on Southwest Airlines.

We grabbed a meeting place with wifi and a whiteboard (very important) from Breather for around $380 for five hours or so.

So if you’re keeping track so far, we spent right around $2,000 or so just to get together and plan out our product roadmap.

Because it’s important.

Day 2: Planning day and IndieHacker Meetup

This is really Day 1 of the trip because it’s the first day we were all together and putting in work.

Caleb (our small angel investor) flew up from Denver and Jeff just rolled out of his bed and hopped in an Uber and we all met at the hotel.

First order of business was some coffee ☕️ near by and some light breakfast and hugs.

We hadn’t seen each other in awhile and seeing each other at all was a real luxury.

We all needed hugs.

We chatted awhile and caught up with each other and then walked over to our Breather workspace for the afternoon.product roadmap

Look at that fresh whiteboard baby!

Progress waiting to be had.

Product Roadmap Objectives

In our case we were rolling out version 2.0 of AccelelrList.

Not only were we adding a bunch of new features, we were also going to be updating the tech from ReactJS to React/Redux on the frontend.

The backend would stay Python and PostgreSQL.

Now usually, product roadmaps are all about features and your product but we wanted to go beyond that as we felt there was more to be tied in as we planned for the future.

As you write code, you have to think about how it affects the entire sales process.

As you write code, you have to think about how it affects the entire sales process. Click To Tweet

When you have to add things later, it can get messy and delay you from your real objectives.

Here was our four objectives for the meeting as we discussed our product roadmap.

  1. Features
  2. Retention
  3. Marketing
  4. Integrations

We spoke a lot about features because we felt like we were missing some.  We spoke a lot about retention because we wanted to reduce our churn.

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Our churn is in the SaaS average currently and most of it is product market fit but we still wanted to ensure we had a solid plan to retain as many users as possible month-over-month.

For marketing, we wanted to be sure we had the right message to attract our ideal customers and the code and features to match it.

And finally, integrations. In our niche, integrations come in handy when trying to add more value to our user base.

When it comes to features, you can’t just add everything your customers are asking for.

You really need to be strategic here.


product roadmap

Sorry not sorry for blurring out our secret sauce

Your features need to be a “win-win” mix for you and the user.

It needs to add tremendous value to your bottom line or bring you up to par with a competitor.

Or some sort of value like that.

For the user, it should be habit forming, if possible.

And before you decide to add that feature, you should be thinking about WHY the user wants that feature.

I love using the “5 Whys” method to truly understanding something before we make a move.

product roadmap

In our niche there is a thousand different (we’re not kidding either) workflows a customer could use to reach their goals so it’s especially important for us to narrow the features down to the ones that the “meat of the market” will be using.

If you don’t have enough features you risk losing marketshare and if you have too many then you’ve just overspent your resources.

If you don't have enough features you risk losing marketshare and if you have too many then you've just overspent your resources. Click To Tweet

You need to know your customer (your avatar) by making sure there is great product market fit and then be strategic about the features you commit to building.

Mentally exhausted and time for a party

The 4 hours we spent in that room was exhausting.


More so because it was so important to get it right.

How often do you work on and release a huge version change to your application?  Not very often.

So we had to get it right.

Our time was up at the Breather workspace so we packed our shit and headed out for some quick dinner.

The next item on the agenda was to get some SaaSpnr social time.

Remember, SaaSpnr = SaaS + Entrepreneur

Is that you?  Tell us why below in the comments.

San Francisco Indie Hacker meetup

If you’re reading this article then you might have arrived here from the IndieHacker community.

If so, welcome brother and sisters!

If not, head over there and check it all out.  It is a fantastic community built by a great guy, Courtland Allen.








product roadmap

Indie Hackers was acquired by Stripe not too long ago to strategically build a base of potential customers and marketing arm like no other.

It’s seriously one of the most thoughtful and growth hacky (yes I said that) things a big tech company could do in my opinion.

Courtland and Stripe wanted to grow the community and influence of the site so they set out to pick IH ambassadors in each city across the globe to host Indie Hacker meet ups.

So we went to the San Francisco one hosted at Southern Pacific Brewery.

And we had a fricking blast!

We meet some really great people. They were brilliant and courageous in their own right.

Being an entrepreneur is lonely and tough and meeting up regularly with other like-minded folks is a great way to keep you on track.

Day 3: We met friends and no longer that lonely.

It’s Friday morning now.  Caleb left to go back to Denver and Jeff and I planned out a solid day of work and brainstorming.

We had a vision and plan and now we needed to talk about how we were going to execute on that plan.

We were both a little tired from the evening before and I saved Courtland from an inadvertent head butt when Jeff got a little too 🍺 tipsy.

That would have been real awkward, right?

What awkward meet up story do you have?  Sound off in the comments below, we want to hear them!

Instead of spending more money on another co-working space we decided to head on over to Workshop Cafe.

I can’t say enough about this place.  What a great idea and I’m not too sure why Starbucks hasn’t copied their model yet.

This place was literally made for startups and for whatever reason, it wasn’t too busy when we were there.

So we got a nice office space for the entire time that we were working. Because I was a new visitor I got 10 free hours to use as well.

Jeff and I powered through some ideas on execution and came up with a solid plan to work for our launch of AccelerList 2.0.

Lunch with another SaaS team.

I’m a huge believer in networking.

If you’re extroverted I know this can be hard but if there is one thing you have to master outside of writing killer code, it’s networking.

We din’t just plan our weekend around working when we put this product roadmap trip together.

We purposely decided to arrange for as many meetings as possible with either partners, mentors, customers or peers.

And for today we planned on having lunch with new friends ServiceBot.io.

They have a similar startup story to us but we’re a little different in that they were open to and actively looking for VC funding.

We had a great lunch and talked about our different niches and value propositions.

We also shared all of our pain points.

Today, we were a little less “lonely”.

We should have got tshirts made up too!  Good call ServiceBot!

After lunch we powered through another afternoon session of work and then met up with Jeff’s awesome girlfriend Mishall.

She is a self taught developer and an all around awesome person.

Did you know there are more men in SF than women which makes it uniquely harder for men to date and find suitable partners?

Do you agree with this?  Leave some comments below and tell us why or why not.

Day 4: We prepare to ship another app and add a new co-founder.

Once we had domain knowledge in our niche and really got to know our customers we felt more comfortable creating new solutions in the same space.

A perfect example of this type of strategy is what Noah Kagan has done with all of his Sumo businesses or what Neil Patel did with KissMetrics and other businesses.

In our case, we wanted to stay in the Amazon space and ship another SaaS app to offer solutions to our existing customer base.

What better way to kickstart your next SaaS app with a base of customers who already want or need your solution?

Jeff is a great full stack developer but he was smart to value the idea of bringing in a partner to do some of the more heavy lifting on the backend of our new app.

I agreed with him.  We were building a algorithm heavy Amazon “repricer” for sellers and we needed a partner who loved data.

Someone who lived and breathed it.

So we brought on Jack.

He’s the guy who crunches hexagonal trigonometry problems in his sleep and then spits them out for breakfast before he heads off to work.

He’s also a great all around guy too.

It was only fair to bring him on as an equity partner for this new application, and so we did.

We hope to build many more applications together as a team!

Dinner with a legend

With Jack on board and having his Saturday free to strategize with us, we worked all afternoon to finish up lose ends before we planned to ship in August 2018.

Before we all met, Jeff had already reached out to someone we looked up to in the Bay area for being a solo founder and a very successful one at that.

I couldn’t believe Jeff was able to grab a meeting with him.  More importantly, a meeting on a Saturday night.

We were going to be having dinner with Vincent from CoderPad.

This is definitely someone we looked up to.

Vincent has bootstrapped his business to $2M+ ARR as a solo founder and developer and he had lots of insights to give us.

So we took him out to a fancy restaurant and wine’d and dined him!

I’m sure he would have met us at a local burger joint too but we wanted his attention and only thought it was fair to take him somewhere nice.

What a treat this was. 

We met with Vincent over dinner for about an hour and a half and gained some very valuable insights.

Two of them being to respect your time and raise your prices.

Vincent wished us good luck and said to reach out if ever had any questions or needed guidance.

We just might do that again one day.

Going home to Los Angeles with renewed energy

I had to flight out early the next morning to Los Angeles so I couldn’t hang too long. 

Jack grabbed an Uber home and Jeff connected with his girlfriend one more time for the weekend.

I got back to my hotel exhausted.

All sorts of ideas and new objectives were running through my head and all I wanted to do was to get home and execute again.

Ever been on a vacation that didn’t really seem like a vacation because it was so much damn work?

Well this was the opposite.

This was a business trip that felt like a vacation because we planned it so well and it ended up being more fun than we originally though it would be.

We’d like to hear your thoughts and comments on our weekend product roadmap trip.  Can you take a minute and post below in the comment section?

Until next time, keep working hard and thank you for reading!  Congrats on being a SaaSpnr too!

Travis R.
growth hacker | founder | husband | father
A devout Chicagoan living in Los Angeles and growth hacking his way to freedom. Pizza 🍕 is life. Know and grow, reach for the ✨ stars. Cubs win the ⚾️ World Series. Let's connect 💻 anytime.

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