Recap and Lessons Learned from the First TinySeed Retreat

We held our first TinySeed founder retreat this past July in Minneapolis, Minnesota: two nights on a ranch a few hours outside of the city and a final night back in the city. 

Since TinySeed is a remote accelerator with founders across 4 countries and 3 continents, it’s important for us to hold regular retreats during the accelerator year to meet and work with them in-person.

We had an amazing time; combining deep work and conversations about our companies and getting in-person help from the entire batch, to delightful hang periods in the afternoons and enjoying the summer weather together. We also learned several things along the way that we’ll apply to future retreats, and thought we’d share some of our learnings publicly.

Lesson #1: Getting everyone in the same room can lead to wonderful, unexpected insights

From left: Paul Kogan (   LessAccounting   ), Craig Hewitt (   Castos   ), Peter Suhm (   Branch   ) and Einar Vollset (TinySeed).

From left: Paul Kogan (LessAccounting), Craig Hewitt (Castos), Peter Suhm (Branch) and Einar Vollset (TinySeed).

From left: Einar Vollset, David Heller (   Reimbi   ), Rob Walling (TinySeed), Andy Hawkes (   Loadster   ).

From left: Einar Vollset, David Heller (Reimbi), Rob Walling (TinySeed), Andy Hawkes (Loadster).

We scheduled an extended chunk of time for dedicated hotseats with each company over the two days at the ranch. A few founders confessed to us beforehand that they weren’t sure they would need the entire chunk of time — but, without fail, we filled up the allotted time and more with active conversation. 

Founders left the retreat with unexpected takeaways to apply to their company between retreats. This was an easy win and something we’ll schedule again at every future retreat.

Lesson #2: Check cell reception and wifi availability before booking a retreat center

Foreground: Sherry Walling (   ZenFounder   , TinySeed mentor). Background, from left: Peter Suhm, Scottie Elliott (   Gather   ), Rob Walling, Paul Kogan.

Foreground: Sherry Walling (ZenFounder, TinySeed mentor). Background, from left: Peter Suhm, Scottie Elliott (Gather), Rob Walling, Paul Kogan.

We looked at many retreat centers in and around Minneapolis and settled on Shire in the Woods as we could give every founder their own room, and essentially have the entire retreat center to ourselves. 

However, there was no cell reception and very slow wifi, which caused a bit of anxiety for our founders who needed a few hours of work while attending the retreat. We all survived, but in the future we’ll be requesting speed tests from the retreat centers and hotels that we’re considering. 

Lesson #3: Be prepared for curveballs (for example, an unusual amount of bugs)

From left: Scottie Elliott, Paul Kogan, Craig Hewitt, Peter Suhm, Einar Vollset, David Heller, Brian Elliott (   Gather   ), Bryan Marble (   ClientRock   ).

From left: Scottie Elliott, Paul Kogan, Craig Hewitt, Peter Suhm, Einar Vollset, David Heller, Brian Elliott (Gather), Bryan Marble (ClientRock).

We knew that Minnesota would be buggy, but not as buggy as it was! The weather the previous week meant we were at peak mosquito-and-flies, meaning our plans to spend time at the outdoor firepit in the evenings were dashed. 

For our second day at the ranch, we decided to go to where we knew there would be no bugs: out on a lake! Thankfully there were pontoon boats available, so we quickly booked one and enjoyed a windy, but bug-free, afternoon together. It was a last minute decision that lead to some of the best time we spent together.

Lesson #4: We opened up the guest list for the final evening, which turned out to be a great decision


For our last evening in Minneapolis, we returned to the city and had one final party, where we invited a few local mentors and LPs to come by and have drinks and dinner with us. After a few nights together with just the founders and TinySeed team, it was great to bring in new voices and conversation, not to mention give our founders a chance to meet some of our mentors in person. 

The retreat ended with a beautiful sunset and a spectacular thunderstorm in the distance with no raindrops on us — the perfect, lucky, summer evening weather. 

Overall, our inaugural TinySeed retreat was a smashing success. We knew our founders were a smart, talented group of people and getting everyone together in person only cemented that impression further. 

Our next retreat will be in Dubrovnik, Croatia, immediately before MicroConf Europe, and we’ll be scheduling two more for this initial batch of companies. Suffice to say, we’re excited for the rest of the accelerator year with these founders and looking forward to our next in-person retreat.

Interested in TinySeed? Add your email here to be notified when applications open for Batch 2 on November 1st.

All photos by Tracy Osborn

RetreatsTracy Osborn