Sept 25 · Pershing, AustinReserve →
SideHustle
Blog
← Back to Blog

Education

The biggest mistakes teachers make when teaching pitching

Five common mistakes that quietly sabotage pitch lessons, and the simple fixes that turn results around fast.

May 3, 2026 · 2 min read

Q: What are the biggest mistakes teachers make when teaching pitching?

The biggest pitch-teaching mistakes are: starting with slides instead of structure, over-coaching charisma, grading by gut instead of rubric, calling on volunteers (always the same students), and skipping peer judging. Fix any one and results jump. Fix all five and the unit transforms.

The story

Teachers who teach pitching well aren't necessarily the most charismatic; they're the most structural. The five mistakes that consistently sabotage pitch units are starting with slide design (slides are the last 10%, not the first), over-coaching charisma (which excludes shy students by design), grading by gut (which feels unfair and is), only calling on volunteers (which calcifies the same dynamic), and skipping peer judging (which leaves students dependent on the teacher's reaction). SideHustle® LIVE Labs avoids most of these by structuring the 60 to 90 minute Labs format around teams, rounds, and Funny + Fundable scoring. Professors and student groups at universities have independently adapted and played the free SideHustle game in their own classrooms. For the foundational teaching method see how to teach pitching to high school students. Structure beats charisma in teaching just as it does in pitching.

What it means

If your pitch unit is producing the same three confident students every year, the problem isn't the kids; it's the structure. Audit your unit against the five mistakes. Fix the worst one first. Repeat next semester. Within a year you'll have a different set of students raising their hands. For the full educator playbook, see the educator guide to teaching entrepreneurship through play.

Try it

Try SideHustle free with your students

SideHustle is edutainment: students pitch funny and fundable business ideas and learn to think on their feet, no slides and no worksheets. It runs in a single class period and scales from a handful of students to a whole grade. Opt in to play free and bring it to class this week.

Frequently Asked Questions

Should beginners ever start with slides?+

No. Slides are the last 10%. Spine and structure first.

Is peer judging too harsh?+

Not with a clear rubric. Peers are often kinder and more specific than expected.

Related Reading

Play SideHustle® LIVE

Pitch Made-Up Businesses For Points

Drop your email and start pitching ridiculous businesses in 60 seconds — free, online, anywhere.

We’ll never sell your info. Access the game online and get updates for upcoming shows and events.