Episode 700 | Playing the Long Game

19 snips

Feb 13, 2024

Exploring the importance of long-term thinking, a founder reflects on balancing short-term gains with strategic planning. Niche market strategies reveal insights on SEO and scaling businesses patiently. Delving into angel investing shows the rewards of relationship-building and persistence. Authenticity takes center stage as a path to credibility in a crowded field. Finally, a journey of 700 episodes highlights the value of hard work, skill development, and gratitude for loyal listeners.

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ADVICE

Don't Compare Your Journey to Others

Avoid comparing your progress to others' highlight reels on social media.
Long-term success often requires sustained effort and planning.

ANECDOTE

Gather's Upmarket Pivot

Gather, featured on Tiny Seed Tales, pivoted upmarket, which took 18 months.
They almost ran out of money due to underestimating the pivot's timeline.

ANECDOTE

WP Engine Investment

Rob Walling's first angel investment, WP Engine, took 7-9 years to pay off significantly.
He considers it his third most lucrative asset.

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In episode 700, Rob goes solo to celebrate another milestone of Startups For the Rest of Us. He reflects on playing the long game and doing so publicly enough to create larger luck surface area. He also emphasizes building skills in the process, and highlights several founders who have done this well.

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Topics we cover:

2:41 – Balancing short vs. long term thinking and decision making
7:30 – Examples of founders leaning into the long game
12:18 – Putting in the time, and doing it publicly (enough)
16:42 – Lucky or smart?
21:22 – How do I know if I’m playing the correct long game?
23:54 – Acquiring skills as you play the long game
27:13 – Cheers to 700!

Links from the Show:

Apply for TinySeed Spring 2024
MicroConf
TinySeed
Start Small, Stay Small by Rob Walling
Gather
TinySeed Tales S2E1 | Introducing Gather
Lucky or Smart? by Bo Peabody

If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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