How to handstand + skateboard without ‘falling on your face’

An illustration of pioneer skateboarder Patti McGee by Veronika Rehm.
Patti McGee (2004) by Veronika Rehm (IG: @veronika.rehm)

Handstand tricks have been around since the early days of skateboarding and even featured on the front of Life magazine, thanks to trailblazers like Patti McGee who demoed them for Hobie Skateboards in the 1960s.

Bert Mathieson flips out of a rail handstand during his run at WFSC 2025 (Germany).

Nowadays, practitioners like Bert Mathieson (IG: @gaspskate) and Ismael Pérez (IG: @isma_pl, YT: @isma_pl) continue to push the boundaries of what can be done upside-down.

The handstand is more of a foundational skill for gymnasts than skaters, making it an intimidating skateboarding trick to learn. We’ve gathered some mates, both local and abroad, to share tips on how to safely approach them.

Chunny Baker (Australia)

Melbourne-based Chunny Baker (IG: @chunbaker, YT: @chunbaker) is a body weight coach with experience in parkour and callisthenics.

When it comes to handstands on or off the board, Chunny emphasises the importance of warm-ups in reducing strain and or injury. ‘Even a small couple of minutes before trying a handstand can make the difference of being more successful and an attempt leaving you complaining about body soreness.’

Mobility exercises should focus on wrists and shoulders. Wrists need the TLC because we’re not walking on our hands in everyday life. Shoulders also need some love because they are ‘complicated’ and ‘a quick mobilisation will drastically help not screwing up the shoulder in a handstand attempt’.

For wrists, Chunny recommends the following:

  1. Wrist circles – in a table-top position with palms on the ground (or any flat surface) gently move the shoulders over the wrists in a circular motion in both directions.
  2. Wrist double circles – same as normal wrist circles, but this version slowly rotates the wrists out like a clock every couple of body circles.
  3. Wrist shakes – shaking wrists in a gentle up and down motion after any weight through the wrists can help relieve tension and allow blood flow back through the wrists.
  4. Wrist sweeps – clasp the hands, palms pressed together, and move the wrists through the full range of motion up and down in a prayer-like movement. Then press the back of the wrists together and repeat the movement.

For shoulders, he shares two exercises:

  1. Arm swings/rotations – moving the arms/shoulders through their range of motion (upward swings, side swings, full circles) will help mobilise and open up the shoulders.
  2. Shoulder shrugs – some light shrugs help prep the shoulders for vertical motion. Bonus points given to those who also do a round with arms raised.
‘A quick wrist prep/warm-up can help save your wrists from screaming at you like an angry Karen’ (Chunny Baker), so do your warm-ups, people. And don’t forget those shoulders!

When he’s not freeskating or longboard dancing, Chunny does a bit of handstand practice on a regular skateboard. When doing these types of handstands, he has noticed that balancing over the trucks’ bolts keeps the weight centred. Spreading the fingers also creates a solid base for balancing. Finally, like with off-board handstands, ‘kicking up both feet together from a tucked position…has less torque and momentum than kicking up one leg at a time, but does require a sturdy base through the hands and a more engaged core’.

Jenna Hoffmann (Germany)

East Frisian Skateboards team rider Jenna Hoffmann (IG: @j_to_the_enna) has been working through the gamut of freestyle-skateboarding trick classes. One of her latest projects is handstand tricks and she has been sharing her progress on the socials.

In her quest to avoid the dreaded banana or scorpion back, Jenna is focusing on straight arms. ‘When your hands touch the floor, it is as if you are pushing the floor completely away from you. This is how you get straight arms.’

A series of photos capturing Jenna Hoffmann's handstand.
Straight arms is one key ingredient for a good handstand, according to Jenna Hoffmann.

A ’rounded back’ is another goal of hers, pressing her stomach against her back and keeping her head between her shoulders. With the hips, a controlled swing is what she’s looking for, to avoid flipping over with the legs.

Josh Dunstone (Australia)

Pro freestyler Josh Dunstone (IG: @jdstonefreestyle), who we have interviewed previously, has been practising rolling handstands to add to his repertoire of gymnast plants and rail handstands.

While we filmed his attempts, we asked him how he bails safely out of this trick. He rattled off a bunch of pointers, including off-board training, clearing pebbles, and taking regular breaks during the skate sesh.

Josh Dunstone discusses handstand safety whilst learning a new handstand trick (Dec 2025).

Terry Synnott (USA)

Mode Skateboards founder and freestyle master Terry Synnott made consistent handstand tricks part of his job while working as a performer for Cirque du Soleil. According to his interview with Villa Freestyle, he even had to do one in front of President Clinton (no pressure!).

Being a handstand veteran, he had a couple of safety tips to share:

Proper handstand form (hips over shoulders over hands) is essential. You should be pushing through your shoulders and straightening your arms, extending your legs, and pointing your toes. Proper form not only looks better, but it also allows for making minor handstand adjustments if you need to make corrections while upside down.

A special consideration for rail handstands is to make sure you are beginning the railstand on a level surface, You should reposition if you happen to set up in a dip in the ground. I find that palming the wheels and gripping them tightly helps lock in well and gives you the necessary stability to stall the handstand. And as with everything, practice and adjust your approach to figure out what works best for you.

A final note

All four practitioners highlighted the importance of good handstand form for successful, injury-free handstand attempts on a skateboard, so invest the time and effort into learning good technique before just ‘winging it’. Best of luck with your handstand attempts and don’t forget to share them with us on your socials.

Skate IQ for freestyle: 2025 in review

Last December, I signed up to the Skate IQ program* run by Tyler Stroud and Mitchie Brusco. After a month of lurking on their community forum and muddling through drills, I penned my thoughts on how Skate IQ could help freestyle skateboarders. Since then, it has been the highest read post of 2025, far more interesting to casual readers than Mike Osterman playing UFO 50 in his downtime or interviews from World Freestyle Skateboarding Championships 2025.

The review is at risk of being dated though because the team at Skate IQ are very good at taking on board feedback. So, as the end of 2025 approaches, here are some more freestyler thoughts on the Skate IQ program.

More pricing options

In my original post, I touched on membership pricing as a potential barrier for entry. Not everyone can afford US$49 each month, especially during a cost of living crisis. Luckily, Skate IQ has since switched over to a tiered membership.

Skate IQ now provides tiered membership: US$9, $29, or $49 per month.

If I was joining now, I’d opt for the ‘premium’ option, which grants access to the ‘Three Phase Program’. This is Mitchie and Tyler’s magical formula for success: a series of drills that help improve fundamentals like kick-pushing, wheelies, and ollie pop. None of it is freestyle-specific (except for wheelies), but much of it will cement flatground skills needed for technical skating. And what is freestyle if not technical skating?

There is no fixed minimum term, hence members have the option of going up or down the tiers, depending on their skate needs and or financial circumstances. For instance, if you’re unable to skate due to injury or if you’ve bills to pay, you could downgrade to the the US$9 ‘standard’ tier, which gives you access to the community forum and allows you to watch Mitchie coach other people. If you’re stuck on a particular street flatground trick, such as a treflip, you could move up to the US$49 ‘VIP’ tier and submit clips for personalised feedback. Or you could try submitting freestyle tricks and make Mitchie’s brain melt a little.

‘One of the best bits are the video reviews of others learning similar stuff which inevitably is not freestyle’ (Laura). Video reviews are available to all Skate IQ members.

More freestyle content

When I first signed up in 2024, the Skate IQ team admitted that they knew very little about freestyle. But Mitchie and Tyler were open to learning more about it, resulting in a collaboration with Andy Anderson that has resulted in various freestyle trick-tip videos.

Powell-Peralta pro and former World Round-Up winner Andy Anderson gives Mitchie (‘that Skate IQ guy’) a crash course in freestyle.

The videos are nowhere near as detailed as Tony Gale’s Freestyle Tricktips. Sometimes videos are captioned with question marks and made-up trick names**. Nevertheless I’m glad that they exist because they introduce freestyle to thousands of freestyle naives. Every time a Skate IQ member who usually classifies 50-50s as grind tricks posts a fingerflip after seeing Mitchie and Andy do it, it’s like a unicorn gave birth to a drop bear; I love it.

More IRL skates

The Skate IQ team started doing meets***, including a recent trip Down Under. They spent a day and a half at Sydney Park and Sydenham Green Skate Park, coaching a bunch of Aussies.

Skate IQ’s first Sydney meet (November 2025) at Sydenham Green Skate Park. Photo credit: Tyler Stroud.

It was sweet meeting some of the online community at a real-world skatepark. I put faces to names, got to have coffee with an X Games medallist, and spent much of my weekend indulging in my favourite hobby. Additionally, it kickstarted regular Skate IQ meets back home in Melbourne.

The transition skaters had a great time following Mitchie around the bowl, Everyone did runs to the best of their ability under his watchful eye, and got to work on his suggestions. There was even a mini ollie workshop for the street-inclined. My friend who also attended the workshop noted that the group was a bit big, but ‘as long as you take initiative to seek Mitchie out and ask him the questions you want, he is patient and gives good tips’.

As for me, it was very much like being at a group skate lesson at a bowl/ramp heavy skatepark with a regular skate instructor. I hid most of the time in the out-of-the-way flatground in the corner; I even skived off to the basketball courts next door for an extended period of time. It made me really hanker for a freestyle-only bootcamp, the kind that’s hosted in Japan or Germany. Most likely I’d still be too shy to ask for advice from the freestyle-equivalent of Mitchie Brusco, but at least I’d be learning via osmosis.

More freestyle talk

I highlighted the scarcity of freestyle up for discussion in the Skate IQ forum back in 2024. Some things have not changed. Threads like ‘The path to gnarly transition ollies! Tips for inching upwards?’ far outweigh ones like ‘Flamingo time’.

To counter this, I have tried to carve out a freestyle-safe space on there. Every week, I post a ‘Freestyle Friday’, sharing clips of my own progress, highlighting other freestyle-related threads, and encouraging members to share their own freestyle progress. Do I receive a lot of practical advice from these posts? Not as much as when as I ask for help on shuvits. 🧐 But I feel like I’ve done good work, imparting enthusiasm and knowledge to those unfamiliar with the discipline.

What’s been great is seeing the Skate IQ team and members’ support of this initiative. ‘Freestyle Friday’ often gets pinned by admin, which leads to more views and engagement. Prolifically active members like Netherlands’ Ruth Fraterman are always pairing me up with other freestyle-curious folk. It’s a wholesome community with nary a troll in sight****.

Final thoughts

Will I be keeping my Skate IQ membership for 2026? Yeah, probably. I’m curious to see where my freestyle-shaped Trojan Horse takes us. Hopefully there will be more Skate IQ x freestyler collabs, and a bunch of Skate IQ members well-versed in both vert and freestyle, as well as a half decent shuvit or ollie from yours truly.

*If either of my reviews convinced you to try Skate IQ for a month or two (or forever), please subscribe using this affiliate link. It will go towards paying my ongoing Skate IQ subscription fees. 🙌 

**Made-up trick names are quite common in freestyle, a byproduct of freestyle-skateboarder isolationism.

***There’s an additional cost on top of membership for attending these structured meets, though there are also free, more informal seshes aptly named ‘Coffee and Skate’ that happen whenever Mitchie and Tyler are in town. For instance, Brisbane was lucky enough to host one in October this year.

****Yep, not one single troll. The Skate IQ forum is a veritable safe space for female millennials who have no hope of ollie kickflipping in the foreseeable future.

5 minutes with Luke Shaw

South Australian freestyle skateboarder Luke Shaw.

Why freestyle?

I just always thought freestyle was really cool and creative. I guess I’m a bit of a contrarian and like things that are out of left field, and back when I started skating no one I saw was really doing it. It felt like doing tricks like caspers, truck stands, and primos weren’t the intended way to ride a skateboard which appealed to me.

I like the fact that you don’t need a spot or an obstacle. You can do it at the end of a driveway or a footpath. I like technical skating—in theory you should be able to learn anything with enough practice. I’m not a huge fan of big, gnarly stuff so freestyle suits me perfectly.

Where is your favourite bit of flatground at the moment? Or the weirdest/most unconventional spot?

Haha, same answer for both questions. I have a weird spare room in my house that miraculously has a concrete floor (it’s a great surface). It’s big enough for freestyle, so I pretty much only skate there these days. I can skate when it’s raining or dark and I don’t have to battle it out with scooter kids at the skatepark so it’s great.

How does that work with the tail scrapes and boards flying everywhere?

I’ve definitely put some dents in the walls, but it’s my house so I don’t care; I’ll patch them when they get too bad. I have some old decks lining the perimeter to try to mitigate that somewhat. I don’t really mind scratching up the cement, it gives it some character. I even Bondo’d a crack in the ground that was annoying me. I usually film there so I have a green screen set up and a few lights and tripods. I’m surprised I haven’t kicked a board into those by accident yet.

You must freestyle skate mostly alone then. What’s the response like when you freestyle in front of other skaters in Adelaide?

I hide it for the most part as street skaters usually react with disgust. 😂 Nah, most people are pretty cool and think that stuff is way harder than it is; skaters seem to be a lot more open-minded these days. I can see why some people hate freestyle though if all they have seen is really lame stuff. I think lots of freestylers have absolutely no taste or restraint and taint our image. 🙃😂

What do you think is the most approachable class of freestyle tricks for skaters who don’t necessarily identify with freestyle (and why)?

Probably caspers or rail stuff. As actual tricks you flip into or out of like street skating, they’re more relatable to ‘normal’ skaters, as opposed to more traditional footwork ‘dancing’ freestyle. I think a lot of people think that footwork, pogoing, footplants, things where your feet touch the ground are kinda wack and they wouldn’t want to touch that kind of skating anyway, so there’s a better chance of them being interested in tricks they might already have a foundation for.

But as a freestyle skateboarder, what is your favourite trick or class of tricks to watch and or do? Like what gets you stoked?

Even though I do freestyle, I’m more inspired by technical street skating than by other freestylers. I get ideas from ledge and manual skating. I might see someone do something like a nollie heelflip nosegrind that could inspire me to do a nollie heelflip nose stall then go into a freestyle trick from that position. I like mixing more ‘street’, ollie-based flip tricks with traditional freestyle tricks. I also do a lot of switch and nollie stuff that you don’t see often in freestyle. I think there’s a few skaters who would be considered street skaters who take some inspiration from freestyle, but I’d say I’m a freestyler who’s inspired by street skating.

So I’m guessing you’re a fan of Andy Anderson and Kilian Martin’s work?

They’re both amazing and what they do is really hard stuff, but I don’t really like the whole ‘coming to a complete stop on a ledge or rail and doing a handstand or truck stand out of it’ thing. I love Rodney of course. I’m a huge fan of Daewon, Mike Osterman, Ronnie Creager, and Sto Strouss. I recently discovered Joey Brezinski who is amazing. I’ll stop what I’m doing and watch anything those guys put out.

Sto Strouss does a trick for Halloween.

Is there a particular skate part of any of the above skaters that you would watch on repeat? We’ve had so many interviewees refer to the old Powell-Peralta videos but it looks like you take inspo from different things so we’re curious.

I am obsessed with Rodney’s part in Rodney Mullen vs. Daewon Song: Round 2 (1999). I love that it actually tells the story of his career up to that point with his freestyle stuff at the start, going into his current (for the time) street skating, then showing what he would be doing in the future…all without any words.

His Globe Opinion (2001) part is so good too.

I love Round 3 (2004), especially Daewon’s part, which is still mind-boggling to this day. Ronnie Creager’s part in What If (2005)? is amazing. I love the whole Darkstar Battalion (2003) video, Chet Thomas and Sven Kilchenmann are so technical. I really like Baker 3 (2005) as well, it’s just so of its time and fun, even though it’s not really the type of skating I do at all.

Like a lot of Aussies, you’ve been skating a regular board until quite recently. What has it been like switching between popsicle and freestyle shapes?

Yeh! The first freestyle board I had ever even seen in real life was from you, [a Smokin’ Sukkaz]! I had been experimenting with different street-board sizes and decided to try an actual freestyle board. I found that it made freestyle stuff a lot easier, but then made my more ‘street’ tricks harder. Even simple stuff I can do most tries on a street board like kickflips or heelflips were really inconsistent and had no pop on a freestyle board, but then truck stands and caspers were way easier.

So I had to decide between that trade-off: easier street tricks/harder freestyle vs. harder street tricks/easier freestyle. I’ve gone back to a street board for now as I find the freestyle tricks on a street board a bit easier than the other way around, so I’m riding 7.75″ decks at the moment. I recently switched to the first (I guess ‘freestyle’?) wheels I’ve tried too, Powell-Peralta Nano Cubics. It’s great actually having the wheels flush or slightly wider than the axles and is making rail tricks a lot easier. I ride 52mm wheels which seems a bit harder to find in freestyle wheels.

Final question: if Rundle Mall’s Balls was a freestyle trick, what would it look like?

Maybe a kickflip to rail. They both take balance, they both get a lot of attention, and neither is quite as impressive as people make them out to be.

Bert Flugelman’s The Spheres (aka ‘Mall’s Balls’) in Adelaide, South Australia. Photo credit: Syed Abdul Khaliq.

Connect: Luke Shaw is a freestyle skateboarder from Adelaide, South Australia. When he’s not skating, he’s doing animator/videographer things like The Household. You’ll rarely catch him rolling around at a skatepark, so find his freestyle on Instagram (@cinderblocz) and TikTok (@cinderblockz).

Drills for better caspers

I’ve been stuck in Casperland for months now. Initially, I’d do thirty exits out of casper stance every skateboarding session to overcome the fear of them. Then I wanted to be able to move into and out of casper. And now? Now, I want to be better at caspers.

better text on blue background
Photo by Kevin Malik on Pexels.com

But what is a casper?

The casper is a skateboarding trick invented by Bobby ‘Casper’ Boyden. The original freestyle-skateboarding version involves flopping the board over using mechanics similar to pulling up into heelside rail. While in ‘casper stance’, one foot is on the graphic side of the kick and the other foot is under the board. To exit, the skater scissor kicks, flipping and rotating the board 180 degrees, to land back on bolts.

Casper problems

Firstly, I have what I like to call ‘casper hesitancy’. I have no trouble getting into casper and holding casper stance but, sometimesmost of the time, I linger there for too long and fall out from fatigue. If I do successfully exit, I look like I’ve purposefully wasted ten seconds of an onlooker’s life. 🙁

I also have a low strike rate. If the casper entry feels off, I just scrap it and start again, which is fine when I’m not worried about consistency. But in contest-run situations? I’m going to have to be less picky with my entries. 🙁 🙁

Lastly, I want a best-practice casper; one that has

  • minimal arm flailing and
  • no foot down (obviously).
multiple exposure of an air dancer
Waving arms around in skateboarding is often a sign of poor control. Photo by Charles Haacker on Pexels.com

So, how do I get to better?

Casper solutions

Mitchie Brusco’s Skate IQ program has made me approach skateboarding a little bit differently. Its emphasis on ten-minute/fifty-rep drills has got me cooking up exercises of my own for freestyle skateboarding.

Over the past few weeks and with some help from the international freestyle community, I’ve come up with four exercises to address the aforementioned casper problems.

Count to three – for all casper entry to exit attempts, count to three and always attempt to exit at ‘three’. If fear, self-doubt, and other negative thoughts are hijacking the brain, get more focused by counting in a different language.

Casper spacewalks – save those imperfect casper entries by working on casper shuffling, that thing freestylers do to correct their foot position in casper stance.

Never Enough skateboarder Paolo Virgilio Demurtas recommends working on casper spacewalks to strengthen this skill. ‘It’s good to try to “recover” and reposition the foot while spacewalking. Gives you a lot of consistency for other casper tricks.’

Scottish rider Egg Spence demonstrates casper spacewalks.

Casper statues – pretend to be a statue while in casper stance. How long can you hold your casper with little or no movement? This is a game MLM skateboarder Dan Harrigan and his mate MadGreek came up with to work on micro corrections for balance, instead of ‘rolling the windows down’ as Dan likes to call it.

Casper spin initiation – in his casper tutorial, Tony Gale notes that any feet on the floor will stop a clean rotation during casper spins. So the best drill for removing this ugly foot-down habit is to practice casper entry into casper spin. If you’re still managing to cheat the spin somehow, try doing the drill on a rubberised surface, the stuff that’s used in playgrounds; if any part of your shoe is touching the ground, it’s going to catch.

A final note

While it’s early days for doing these drills, I’ve already noticed an improvement in my caspers. Count to three, for instance, has already boosted my ‘just commit’ mindset as well as improving trick flow. I’m really excited to see where casper spacewalk, casper statues, and casper spin initiation take me.

Did you find these exercises helpful? Or do you have your own casper-specific hacks that you want to share? Let us know in the comments below, or get in touch with us via Instagram (@flatlandiafreestyle).

5 minutes with Mike Osterman

Mike Osterman in the Waltz Skateboarding ‘garage’.

Why did you choose freestyle?

I grew up in the middle of the country, about an hour outside of Chicago, and didn’t have easy access to any parks or decent skate spots. I also played a lot of Tony Hawk’s Pro Skater, so I was exposed to freestyle tricks that way. I think the combination of no parks and exposure to freestyle tricks led me to learn that stuff. Then I read Rodney’s book and discovered that it all had a name, competitions, forums, etc. Luckily the forums and grainy online videos in 2006 didn’t scare me away. 

Did you ever do any transition or street skating?

I did a tiny bit of street skating. Mostly curbs and manual pads. I’m terrible at that stuff.

Same with transitions. I used to work at Jeric’s Skate Shop in Plainfield, Illinois. They had a two-foot mini ramp in the shop and I could barely ride it, despite spending most of my time there, haha.

How long have you been skating for?

I started skating in 2005 so I guess that makes twenty years now. And now I feel very old. 

How much time does running Waltz Skateboarding leave you to skate for yourself?

Zero time units. Seriously though, I try to have at least one session per week. We meet with the Long Beach freestyle crew every Sunday so that keeps me on my board. I’m grateful for that. I’ll sneak off for a lunchbreak session now and then as well. That’s always nice. 

When did you start Waltz?

Daniel Trujillo and I officially started Waltz in April of 2018. We made a few t-shirts before that, but 2018 is when we made the leap and made it legit.

What inspires you to keep Waltz running?

Jamie Wong makes me keep it all running. The goal of Waltz has been to grow the community and make decent gear for them. A lot of people really love being part of a freestyle scene—online or in their towns. That’s been a huge motivator. The US Open was a really emotional experience for that reason—seeing so many people come together to support our local scene and each other was surreal. I just want to do more of that.

What’s the hardest part of your job of running a freestyle company?

I think the hardest part of running Waltz right now is finding a way to make all of the things that we want to. Freestyle gear is hard to make. Period. Most factories, especially those in the USA, have dialled in their processes to churn out standard skateboard shapes (both wheels and decks) SUPER efficiently. That’s how they stay competitive. I’m SUPER grateful to work with a handful of smaller factories that are down to get weird—pressing with custom moulds, accepting relatively low order minimums, developing custom wheel moulds, etc. 

Still, with the broad range of sizes and shapes that folks ride, it’s extremely difficult to make a board to serve every person’s preferences. There’s always that one guy who wants a 7.51255″ instead of a 7.4″ or a 7.75″. And the wheelbase is never right. Still, I do my best to stock a couple shapes in each of our concave families. Making the ‘best freestyle board’ means serving a wide range of freestylers.

That same challenge applies to every other part of Waltz’s work. Media, events, even our community forums like our Discord. Waltz can’t make everything. We can’t be everything for everyone, so I spend a lot of time trying to temper my enthusiasm. 😀 Someone else can make the Freestyle Brazil Tour Video.

What do you have planned for Waltz in the future?

Ugh, hopefully more nap time. Two new pro models dropping in 2026 if we can get our act together. 😄 More trick tips. We’re discontinuing Waltz Wheels (cue sad music) and maybe a new collab with an old friend? Is that cryptic enough?

What does Mike Osterman do when he’s not skating and making boards?

I’m pretty boring. I love going on walks around Long Beach. Maria and I spent a lot of time in Japan just walking. When I’m injured, I usually end up playing a lot of video games—playing a lot of UFO 50 lately.

Connect: Mike Osterman is the co-founder of Waltz Skateboarding, organiser of the US Open of Freestyle Skateboarding, and captain of the Long Beach freestyle crew (Instagram: @lbcfreestyle). Basically he wears many hats, which is why his pro board has a bunch of hats on it. Follow him on Instagram (@mike_osterman) and YouTube (@mike_osterman1). If you want a Mike Osterman board and or other Waltz Skateboarding models, you’ll find them stocked at Aikenheads (Perth, WA).