This post is a part of our Unexpected Sources of Inspiration series where we share how inspiration sometimes comes from the unlikeliest of places. I’m Jason, Head of Design at Plain Sight Ventures, and your friend in the design-nerd world. Feel free to reach out to me at jason@plainsightventures.co if you want to connect about design things or coffee or running or really just anything!

Despite every warning of dreary, rainy, bone-chilling cold weather, I recently took a fall trip to the Scandinavian wonderland of Denmark and Sweden. Though the weather warnings were spot-on, I was surprised at how little the weather actually mattered. Constantly immersed in cobblestone streets packed with age-old stone buildings next to minimalist modern newcomers, the cold really just seems to fade away and you actually look forward to layering up and packing into hip little coffeeshops like La Cabra, Coffee Collectif, or April. It also helps that yummy baked goods are everywhere you look, helping to insulate you for the short daylight and windy nights.

The first thing most people think of when you mention Denmark or Sweden or Scandinavia in any capacity is…IKEA. There’s a good reason for that. IKEA has made minimalist, modern Scandinavian design aesthetics approachable and accessible to everyday consumers whether you’re in New York or Ohio. IKEA’s democratic design principles of “function, form, quality, sustainability, and low price” has been (mostly) a force for good design, pushing the notion that minimalism and intentional use of space is optimal for good living.

It’s hard to explain just how right it feels to live day-to-day in Scandinavia. There’s a system and a balance and a calm to things that just doesn’t really exist here in the States. The sheer use of “space” is something that lends itself to all facets of daily life, and you really do find yourself leaving room for the unknown and learning to appreciate gaps, whether they be gaps in your schedule or in conversations or in a park. This was certainly a big moment for me as a designer.

So often, designers try to use all available space to squeeze in content or functionality or graphics - but we can learn from Scandi design that space doesn’t have to be filled. Sometimes, creating space can be intentional and a way to make information more easily digestible or add emphasis to something or just a nice break for the eyes and brain.

Back home in Austin, I’m now trying to be more intentional about giving things, all things, just a little more patience and room to breathe. Creating space for space’s sake is an important skill to add to designer’s toolkit and a principle that I hope to inject into each and every project from PSV. That, and of course, hot cardamom buns for every meeting.

I’ve been going through some of my favorite sales and partnership tools in our tech stack and wanted to share another fantastic one called Crossbeam. Crossbeam is a collaborative data platform that helps companies build more valuable partnerships, and it’s one that should be in every partner team’s toolkit.

Here’s why I love it:

1. It allows you to account map with a completely different company by simply integrating your CRM. (We’re big fans of simple integrations over here at PSV. 😉)
2. It shows you what shared customers, opportunities, and leads you have in common. This is great for you to be able to make warm referrals, co-market, and co-sell. It also helps you make sure if a partnership even makes sense at that time. If you don’t have any shared customers, you at least know what you’re getting into.
3. The best part is that Crossbeam allows you to do all of this securely and only shows you matching accounts, leads or opportunities. You aren’t giving your whole list to somebody else.

Curious if you find Crossbeam helpful or if you have another comparable tool that you like even more! Hit me up on LinkedIn and let’s swap tools.

Brands are often thought of as nice-to-have’s — something you get to later, long after the product has shipped and meaningful revenue has been secured. And while many startups have found success with that approach, it doesn’t work for everyone. Because brands are not just a function of marketing or an attempt to glossy up your website — brands provide clear direction on who you are as a company, why you matter, and how you offer value to your customers, employees, and key stakeholders. The problem you’re solving gives your team purpose, and a brand provides alignment toward that purpose.

It also gives your customers a sense for who you are as a company and what they may expect if they buy your product. This isn’t to say that your team can’t express individuality, but a brand is going to ensure some alignment in promises and how those promises are communicated.

If you are a solo founder, creating a single product, and hold every title from CEO to support rep, one can assume that you are going to give a customer a consistent experience. However, as soon as you start adding team members, developing a brand can be helpful in aligning the team and increasing momentum as a company.

Now, I know early on there’s not going to be a lot of time for this. And it is likely that you’ll shift your brand tone as you find yourself in the market. But this isn’t enough reason to avoid it completely. Because just like not choosing a direction is choosing a direction… not choosing a brand is actually choosing a brand. It’ll just be a bad one.

At PSV, we’re constantly thinking of new product ideas. This means that we have to move quickly on developing a brand so we can ship things. Not every product has an involved branding process, but we do have a discussion about it. And after a couple years of going ‘round the horn with this, I wanted to share a few tips:

1. Go with the Minimum Viable Brand
   ‍If you’re on an agile team who can’t be bothered with branding, go with the MVB approach. I’m convinced if you just put “Minimum Viable…” in front of anything you want to do, it’ll be received better. Just like with a MVP (minimum viable product), you’re presenting a low-stakes, focused approached to what you want to build. There is plenty of content out there about how to create a Minimum Viable Brand, including this blog post from our friends over at High Alpha, so I won’t go into the details here. But read up on this and learn to cut out as much as you can.
   
   If you have an agency or corporate background and are used to months of back-and-forth on brand development, this will either feel really good to do or really bad. But either way it’s necessary.
   
   I’d recommend reading up on MVBs to get your process down, and the following tips are how to make that process go a bit faster.
   ‍
2. ‍Multiple choice vs. open-ended brainstorm
   ‍Now this one is going to be dependent on if you have a brand champion or marketing expert on your team who is willing to put in the prep work. One of the things that takes branding work so long is the unending back-and-forth “brainstorm” with what is usually way too many people.
   
   To avoid this, for everything you need to decide, make it multiple choice. If you want to define your Brand Values, provide a list of words to choose from. If you want to define your Brand Personality, put each one on a numbered scale and let people pick a number. Whatever you do, don’t let them veer off into uncharted brainstorming territory — this is where the time suck happens. Create clear and boundaried options so you're not working with a blank canvas. This will help everyone move forward together, and faster.
   ‍
3. Optimize everyone’s time
   ‍This is related to the previous point, but I find that on a small team that’s used to moving quickly, two-hour branding meetings tend to drain everyone — except me, but that’s because I love this work. However, I can admit it isn’t the best use of everyone’s time, even though I do want buy-in and agreement.
   
   So to keep everyone in good spirits, I’ll actually take all those questions around our brand values and personality traits and Slack each person individually with a deadline for their response. That way, no one is influenced and everyone can quickly decide what they think. Moving this quickly is okay because the reality is we may change things later. So the goal here is to get clarity on where everyone’s heads are at so that we can surface any large objections about what we offer and how we’re communicating that offer.
   ‍
4. ‍Come together for agreement (or timed debate)
   ‍Once everyone’s answers are sent, we get together for about 30 minutes to an hour to discuss our choices and debate any strong opinions. At this point you will start to get into the nuances of language, and while it can seem like you’re arguing semantics — those semantics will matter. For example, see if you can tell the difference between…
   
   Bold vs Aggressive
   Friendly vs Playful
   Innovative vs Creative
   
   These words can often be interchanged, but when you read them… you sense there is a difference, yes? Choosing the right words to go with will make every step after this much easier, because the next move is to…
   ‍‍
5. Choose a brand archetype
   ‍Working with a blank canvas when it comes to anything creative can be daunting. This is why I rely heavily on the 12 Brand Archetypes. While there may be different flavors and style differences within each archetype, nearly every brand will fall into one pretty clearly. This stage is where people who do not work in marketing can start to make sense of all my nagging questions that preceded this step. ;)
   
   Once we have decided what our value and personality traits are, I take those words and attempt to match them with a brand personality. (Ex: The Jester is “playful” but the Everyman is “friendly.”)
   
   I also take into consideration the product offering, us as a team, and the reality that there are only four of us so our internal personalities will likely impact how we present ourselves to the world. For the most part our team is innovative, risk-taking, friendly, and spontaneous. These attributes are unwavering and will be applied to every PSV project we build. So maybe ask yourself, how does your team or leadership impact your brand archetype?
   
   It shouldn’t take long to eliminate at least half the options. But the work isn’t over just yet. I also map any competitors or folks in our space who have a strong hold on any single archetype. If I think someone out there has taken hold of “Magician,” and it’s one of our top archetypes, chances are I will remove it. I want to make sure our brand stands out as much as possible, and while it’s okay for multiple companies to have a similar brand — that’s not who we are.
   
   At this point, there are usually only one or two options left and most times it becomes clear which one we want select. It's a collective gut feeling at that point. Or I'm left to simply choose it. I’ve yet to narrow it down to something we don’t like or feel is true to who we are and what we offer.
   ‍
6. ‍Let it simmer and see how it fits
   ‍If done well, everything above should take under a week to complete. And there’s reason for that. Whizzing through this work allows your team to understand the process and rehearse how it is integrated.
   
   Depending on where we are with a project, it’s possible we launch a simple website with the chosen archetype in mind to see how it feels. We'll also refer to customer conversations and compare it to some of the words we've chosen. Or maybe we dig deeper and conduct more involved research on that brand archetype and how we want to build it out. Either way, we start to weave that brand into our conversations with customers, and make note of whether it feels right.

None of this is rocket science. In fact, much of it is on intuition. But in order to make sure everyone’s intuition is moving forward together, setting up a clear process and getting buy-in early will help.

If you want more tips on how to get your MVB started or have ideas of your own to share, I’d love to connect!

This post is a part of our Unexpected Sources of Inspiration series where we share how inspiration sometimes comes from the unlikeliest of places. I’m Jason, Head of Design at Plain Sight Ventures, and your friend in the design-nerd world. Feel free to reach out to me at jason@plainsightventures.co if you want to connect about design things or coffee or running or really just anything!

I’m currently in Montreal, QC strolling around what might just be the hippest neighborhood I’ve ever been in. Montreal’s Mont-Royal neighborhood feels like stepping into a Kinfolk spread filled with the most effortlessly cool creatives brandished with a laissez-faire sensibility and a deep understanding of curated chic.

Everything here catches your eye…from concert plasters to sandwich shops to metro signs. Montreal is a designer’s paradise that gives you a year’s worth of inspiration in just a few short walkabouts. Though I could wax design-nerd poetic about all the sights and sounds of Montreal and provide a running count of how many times I’ve actually said out loud “I could totally live here”, I’ll instead just briefly mention one unexpected design-forward coffee shop I stumbled into on my first day here.

‍Café Bravo is a coffee, records, and goodies shop from Bravo Music that somehow leans super heavily into retro 70’s Studio 54 vibes while still feeling totally contemporary and fresh. Their use of bright orange funk and Massimo Vignelli-esque typography grabs you from the street and pulls you into their little space of coffee music magic. I flipped through indie records, poked at merch from local artists, and just took it all in to save this inspo moment for some fun brand work down the road. And after walking back outside filled with the continuously groovy, imaginative spirit of Montreal, I once again declared…”Yeah, I could totally live here.”

This post is part of a peer interview series where we invite folks in partnership roles to share their insight and advice. If you are interested in talking with us and sharing your experience and wisdom, feel free to email me at gabe@plainsightventure.co.

Today’s interview is with a former colleague of mine, Zak Pines, VP of Partnerships at Formstack. Zak has worked in the SaaS space for the last couple decades — leading, managing, and grinding through every growth stage from $0 to $100M+/ARR. I was excited to have him kick this series off. Let’s get into it!

Let’s start with you sharing more about your role at Formstack.

I head up the Formstack partnerships team, which includes technology partners. These are companies who have integrations with Formstack and/or ecosystems we are playing in, our community of consulting partners, and companies who recommend and implement Formstack for customers. I work closely with all Formstack departments and teams to deliver the best possible experience for our partners and grow the revenue contribution of partners to Formstack.

How did you get into this role?

I joined Formstack in late 2018 when they acquired Bedrock Data. The best way to describe my role at Bedrock was a go-to-market jack-of-all-trades; if you mapped my role at Bedrock to Formstack job functions, it would span something like seven different roles. A few months after joining Formstack, Beau Brooks and Dustin Sapp pitched the idea of starting up the partner team along with you. I had a very rewarding three years working with you; we were like-minded and naturally aligned, but also complemented each other really well by balancing each other’s strengths and weaknesses, learning from each other and challenging each other. The Formstack partner team was off and running from there, and the rest is history.

What’s interesting is now looking back at my career, partnerships has been a through-line to every one of my past roles. It’s such a differentiated growth strategy for any business. At IBM I helped create the software that was the foundation for the IBM-NBA partnership. At LiveTechnology, our GTM strategy was based on creating win-win partnerships with agencies to deliver marketing automation solutions to their customers. I was one of the first five Marketo consulting partners at Avitage. At Ipswitch, both MSP and reseller partnerships were key to our growth especially internationally. And at Bedrock Data, we had a technology-partner driven growth strategy with HubSpot as our top ecosystem. I’ve been able to draw from each of those experiences in building the Formstack partner strategy and program. 

What are the biggest challenges for a partnership role?

A partnership role is by definition multi-faceted and cross functional, because partners touch every facet of a business, whether you realize it or not. It requires partner team members to be agile and really effective at communicating both internally and externally with partners. We need to continually be working across multiple planes — the day-to-day alignment partners require, thinking ahead to the next key initiatives, and building out growth plans for the business to maximize impact from partnerships.

How has the role of partnerships in tech changed over time?

One of the reasons I was excited about focusing on partnerships when given the opportunity at Formstack is that the evolution of the partnerships function reminded me of the evolution of the marketing function about a decade earlier. At that point, the concept of revenue marketing meant marketers were focused on the business impact of marketing and driving growth. Partnerships for many companies historically has been a soft function, hard to measure and not seated at the revenue table. Technology today gives us greater ability to measure the impact of partnerships and connect to revenue and growth metrics, and therefore take more accountability for revenue.

Any hot tips/hacks you’ve learned over time?

I’ll give you a few across a range of topics:

• Know your partner persona inside and out
  Spend time with partners. Ask them questions. Learn from them. Make sure you know what makes them tick as that is going to drive so many decisions you make on how to recruit partners and create mutual benefit.
• Celebrate wins
  It will make the progress you’re making with partners, and the impact they are making, more visible. Also, acknowledge cross-functional team members for the work they do to help partners be more successful.
• Be a power user of your CRM
  ‍It should be the lifeblood of your reporting, partner database and communications. Act accordingly — keep your partner data clean, and always connect opportunities back to partners.
• Be responsive
  ‍The reason this is so important is you are now working with another companies’ parameters and deadlines and requirements and goals. If you lean in on responsiveness, partners will know they can trust that you’ll be there for them when they need you.
• Become a product expert
  Know your products. Use your products. Love your products. It’s the currency in which your partners and customers operate, after all.

Favorite tools in your tech stack?

I’m a big believer in the “eat your own dog food” / “drink your own champagne” mantra. I always say the partner team is the number one user of Formstack. When you become a Formstack partner, we ask you to fill out a Formstack for Salesforce form — but it’s not just any form, it’s a prefilled form that serves as your partner profile, fed with data out of Salesforce. Our partner certificates are built using Formstack Documents. We use Formstack Sign wherever possible to manage document signatures. When we run events, we manage registration using Formstack Forms (like this one). You get the idea.

Any career advice for people getting into this role?

Not specific to partnerships, but my advice is take advantage of any opportunity big or small. Any breakthrough I’ve ever had in my career journey has been because I “went for it” at a given moment in time. I spoke to the right person at the right time, followed up with the right message, and the right level of persistence. A great example is an outstanding member of my team at Formstack, Amanda Nielsen. I came to meet Amanda because she introduced herself to me at INBOUND 2016 or 2017, and a couple years later she became a key member of our partner team at Formstack.
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If you’re interested in connecting with Zak, be sure to find him on LinkedIn. Also be sure to check out his post on Formstack 12 Steps to Building Brand, Community & Revenue with Partnerships.

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We talk a lot about JTBD and how best to approach product strategy here at PSV. And we’ve seen a ton of content on it all. This interview definitely clicked more for me than any other. Give it a listen and let me know what you think.

Here are some of the takeaways we’re talking about on our team…

1. "You need to study the struggling moment and determine what NOT to build."  This reminded me of Breena's post last week about chasing rabbits. It's a tough challenge, but there's a difference between being reactive vs being strategic when it comes to customer feedback and building what they need (and what they say they need).
2. More features often create more anxiety. People often wonder, “can it actually do all those things?” Don't just keep adding features, focus on delivering value.
3. Stop trying to sell to people, and instead help them make progress, help them buy. Design the sales process on how people want to buy, which means going back to that context… where were they in that moment of struggling, rewind to get the full picture.
4. "Bitchin' ain't switchin'"... this just made me laugh. A lot of customers will get upset that you aren't adding the features they want, but most of them won't leave because of it.

This post is a part of our Moments of Delight series where we share product (and other) experiences that surprise, inspire, and enchant us. I’m Jason, Head of Design at Plain Sight Ventures, and your friendly neighborhood DesignMan. Feel free to reach out to me at jason@plainsightventures.co if you want to connect about design things or coffee or running or really just anything!

If you’re new to the Browser Wars, Arc is the mind-blowing browser from The Browser Company that "doesn’t just meet your needs — it anticipates them.” For the first time in I don’t even know how long, a browser actually changed the way that I interact with websites. That’s no small thing. I could turn this post into a 10-part series to cover all the things I love about Arc, but for today I just wanted to focus on one little thing they do incredibly well: release notes.

What’s the first thought that comes to mind when you hear “release notes”? I’m going to guess that it’s either “close notification” or “please spare me”. In the realm of software updates, where mundane release notes often read like a dry technical manual, the Arc Browser team has rewritten the script on engaging communication. With every new update, they manage to turn what might be considered a routine announcement into a source of surprising joy and pure delight for their users. I’ve tried to boil the experience down into a few things they’re doing differently:

1. The Art of Storytelling

Imagine opening a software update and being welcomed into a world of storytelling. Arc Browser's release notes aren’t just bullet points; they're narratives. They take users on a journey, weaving a tale of each update's conception, development, and ultimate realization. This approach transcends the mere technical and invites users into the creative process behind each enhancement. Suddenly, what could be a mundane task becomes an invitation to explore and appreciate the dedication of the team. They also do some incredible “behind the scenes” working sessions that have inspired my day-to-day approach to product design.

2. Humanizing the Process

Arc Browser's release notes have an uncanny ability to humanize the development process. They shed light on the team's challenges, eureka moments, and even occasional goof-ups. By openly sharing the ups and downs of their journey, the team breaks down the barriers between developers and users. This transparency not only fosters a sense of connection but also builds trust. Users are no longer just passive recipients of updates; they are part of the narrative, invested in the product's evolution.

3. A Touch of Humor

In a landscape often dominated by technical jargon, Arc Browser's release notes introduce an element of surprise with their humor. Embedded jokes, pop culture references (see Sonic the Hedgehog), and witty anecdotes sprinkle a dose of light-heartedness into what can often be a serious arena. Users find themselves chuckling amidst the patch notes, turning what might be a brief encounter into a memorable moment of genuine amusement.

4. Celebrating the User

The Arc team knows how to make their users feel like heroes. By framing updates as solutions to user pain points and needs, the team shifts the focus from what's new for them to what's improved for the user. This approach elevates the user's role in the product's evolution, making them an integral part of the story rather than a passive observer. Arc often attributes product updates to a user or group of users that reached out to recommend the feature. And when they officially launched, they included each and every beta user’s name in their appreciation credits - you actually felt like you had a hand in building Arc.

5. Visual Delights

Release notes often suffer from a lack of visual appeal, but not when it comes to Arc’s style. Each update is accompanied by vibrant visuals that resonate with the theme of the release. These visuals not only enhance the user's understanding of the changes but also contribute to the overall sense of joy that the release notes evoke. The product shots are real while polished, helpful while engaging, and a mini-source of inspiration for aspiring and working designers.

In the oftentimes vanilla landscape of software development, where updates are frequent and often overlooked, Arc Browser's release notes shine as beacons of exceptional communication and a knowing nod to their user base. They remind us that even in the world of bits and bytes, there's room for creativity, empathy, and genuine human connection. So the next time you see the little updates notification in Arc, take a moment to relish the experience, for you're not just updating software — you're being treated to a delightful chapter in a captivating story.

“Beginner’s mind” — I don’t know a more popular phrase among founders on the Internet. It’s like everyone listened to the same podcast and suddenly decided they wanted to apply Zen Buddhist teachings to their business. And while I whole heartedly believe in this concept of intellectual humility — in practice, most founders struggle to follow through with it.

I get it though. When you’re in the early days of a startup, chasing rabbits is exciting! After all, if you’re not sure what will work, how can you be certain what won’t? So we follow every idea to the bottom of the hole it came from and while we're down there, it's hard to find our way back. It's hard to let go of all the work we put in. So we stay there, in the dark, clinging to our bad, bad rabbit.

“What is beginner’s mind? It’s dropping our expectations and preconceived ideas about something, and seeing things with an open mind, fresh eyes, just like a beginner. If you’ve ever learned something new, you can remember what that’s like: you’re probably confused, because you don’t know how to do whatever you’re learning, but you’re also looking at everything as if it’s brand new, perhaps with curiosity and wonder. That’s beginner’s mind.”
— Zen Habits

I’ve seen it countless times in startups I worked for as well as consulted. Founders have a hard time breaking away from their original execution plan. They grip so tightly to the how of their business that they dislodge themselves from the why completely.

They chase rabbits down their little rabbit holes. They abandon their team. And they lose track of where they’re going. It’s actually remarkable how many teams I’ve seen fall apart simply due to this Alice in Wonderland syndrome.

Of course, good leaders know how to corral, and accept, the chaos. Chasing bad ideas into the ground is part of the whole founder experience. But without a trusting team holding the rope, you may find yourself alone and out of luck in the dark.

As a team who moves quickly on multiple projects a day, trust is a big part of how we function. It is really difficult to know when to cut something loose and when to let our wandering spirit take the lead — trust helps guide us. It keeps our ego in check and fosters the kind of creativity and curiosity required to be successful.

To be honest, this whole founder experience feels like a comical paradox reflecting life itself...

‍How do we balance the creative spontaneity with the day-to-day minutia?
How do we balance past experience with open-mindedness to the new?
How do we let ourselves begin again, over and over and over, without losing sight of who we are and where we’re going?

I clearly don’t have all the answers. But I’ve spent over 15 years mediating conversations between founders — being an emotional counselor to some — and then running my own business for the last nine years. To be frank, it’s all hard. And no matter what they say on a podcast or quippy LinkedIn post, most founders are suffering from some sort of chronic illness alongside their pursuit of success. So take your own wellbeing into account when heeding advice, including this.

Here are some things I’ve learned help curb the rabbit chasing and keep your team anchored to your why:

Write the press release

‍I don’t know where this came from originally. I feel like the startup world is such an echo chamber of the same advice (including this post), but this one repeatedly surfaces for good reason. A press release is succinct. They are usually only one page, which means you have to be thoughtful about what words you choose. And when you’re that meticulous, you’re bound to find the nugget of your why.

This is also great because it doubles as a sort of manifestation practice. It’s aspirational. You can write a press release for a month from now or a year from now. No matter the date, it gives your entire company a peek into what leadership desires. There are no OKRs, there are no bulleted lists of what to do, it’s your vision in a single document.

Build a process that lets you brain dump

‍At PSV, we have an ongoing list of ideas in Notion we’d like to bring to the table. They are categorized as, surprise, “Ideas” and they stay there until we’ve decided they can move forward as a project we want to pursue. We had many meetings about what those parameters are, but we narrowed it down to 3-5 items that these ideas have to pass. There is some flexibility there, but we stick to principles similar to the Ikigai concept:

• What are we good at doing?
• What do we love to do?
• What can we get paid for?
• What does the world need?
• The important thing is that you have a central place where you can brain dump anything and everything, then have a strong filter for when those ideas are allowed to move forward. You must decide these parameters as a team, before generating ideas. This allows for a democratic approach to the process, and more importantly, gives your entire team permission to hold leaders accountable when they stray from this agreed upon list of requirements.

Talk to your target customers early and OFTEN

‍This seems obvious, but it’s amazing how quickly startups lose sight of their own customers. They get a few nuggets here and there of validation, and they are off to the races! So it’s important that you keep talking to people. Nothing keeps an unruly founder in check more than customer feedback. It is another way your team can hold each other accountable if there’s a disagreement on how to move forward.

Allow for divergent conversations

‍This may seem counter-intuitive and contradictory to the previous advice, but stay with me. Similar to us braindumping ideas in Notion, our team also needs time to do so live. For the sake of our relationships and our business, we need to riff as a team. We need to co-create ideas, good and bad, in order to break out of any stiff routine we’ve developed over time. This is when we can find our way back to the beginning. It’s where new ideas can form.

And if you’re on a larger team, these conversations are where leadership should be signing permission slips to forgo unsuccessful ideas thus far. Management and individual contributors will run bad ideas to the depths of the earth if their founders tell them to do so. So release as much as you can during these conversations and make it clear that people are allowed to give honest feedback. But you better be able to actually hear it or else you will break their trust, and they’ll never give honest feedback again.

So schedule these conversations. Stick to the timeframe you allotted. And allow for open feedback and listen.

Don’t overcorrect

‍Sometimes divergent conversations help clarify, and sometimes they lead you straight into the darkness again. Just like with anything good in this world, it requires balance. You have to know how much rope to give so you don’t run out. So let your team sparkle with new ideas and insight, and then ground them with a process that helps them anchor it into your original why. (Reference the press release and the process to keep things under control.)

But if you recently experienced a failure with a feature, an idea, a bad hire, don’t overcorrect. You’ll just risk repeating it and confusing everyone in the process. Go slow and be methodical about a decision that didn’t work out. And most of all, be honest — even if it as the expense of your pride.

As you can see, there isn’t a perfect formula. Every situation is going to be different and depending on the stage, the people on your team, and likely a hundred other factors — what works for you will look different. But sometimes just knowing this can help. Good founders take advice as something to consider, not assign.

So I’ll leave you with this — don’t take any of this so seriously. This will be your downfall (another life lesson I’ve learned). If you can admit when you’ve gone too far or that you’ve chased a bad rabbit idea into the ground, that is more than most can do. So build a process that helps pull you out when needed, trust that your colleagues may know more than you, and allow for curiosity (and fun) to guide you when it feels right as a team.

Be kind, stay open. And most of all, remember you chose this path so you might as well enjoy the ride. ✌️

“When you read biographies of people who've done great work, it's remarkable how much luck is involved. They discover what to work on as a result of a chance meeting, or by reading a book they happen to pick up. So you need to make yourself a big target for luck, and the way to do that is to be curious. Try lots of things, meet lots of people, read lots of books, ask lots of questions.” — Paul Graham, How to Do Great Work

It’s no secret that most startups fail. Just log into LinkedIn, and you’re likely to see dozens of entrepreneurs slinging statistics about how their idea beat all odds of success. And while those stories are inspiring, it’s hard to figure out how to act on them. How do you follow in their footsteps? What action can you take today?

There are a number of things that have to go right for a startup to be successful and the truth is most of it comes down to luck. In his essay How to Do Great Work, Paul Graham talks about how curiosity is what makes you a bigger target for this luck. If you keep asking questions, try different things, eventually, your field of luck will get bigger and bigger.

Another thing that makes you a bigger target for luck? Belief. You have to believe so aggressively in your vision that even on your worst day, you can still push forward through the mud and get the job done. It’s that grit that Angela Duckworth talks about in her TEDTalk.

Sometimes this belief, this grit, looks like walking around in the dark for weeks, maybe even months, in pursuit of what will work for your business. Other times it looks like taking action without the slightest clue if it will work. But what it doesn’t look like is leaning back because you’re afraid. What it doesn’t look like is perfection-induced procrastination. You must always be moving. Period.

When I was building WebMerge, I was working around the clock. I was building custom features for customers, writing blog posts, answering support tickets — it was non-stop. I barely spent time researching competitors because I was too busy focusing on what I believed would be the best solution for people paying me. I didn’t make a plan. I didn’t look 6-9 months in the future. I didn’t do a lot of things that other startups do. I just kept my head down, chipping away at the next task.

And one thing I asked myself at the end of each day, when I was just about to close things down was… what is one more thing I can do in less than 20 minutes?

This seems like a trivial thing, but pushing that extra bit at the end of the day can make all the difference. Developing that discipline to push for 20 more minutes could be enough to close a deal or unblock a teammate. And because I never knew what action would unlock that, if there was something to be done… I had to go for it.

Time-blocking it is key. While you’re bound to go over 20 minutes here and here, the limitation allows you to hyper-focus on something specific. It also prevents you from taking on a bulky strategic task that is better suited for a clear head the next day. It also makes it attainable and less prone to procrastinating.

Tasks that fall in this category can be:

• Answer one more support ticket
• Respond to a coworker’s message
• Review the next days tasks and prioritize them
• Review any unanswered emails and respond
• Review Notion notifications (where we manage our projects)
• Give props to a colleague in Slack (equally important to action in those early days is team morale!)
• Read an article you have bookmarked
• Write down ideas you have — uninterrupted 20-minute brainstorm

Now, this approach isn’t going to work for everyone. And that is precisely why you should do it. Your competitors who clock out at a certain time or who have a tendency to overthink their next move… they’re not going to be able to get in and get out like this. Plus, a lot of people assume small tasks like this won’t matter — they want to go big or go home, when they should go 20 more minutes and then go home.

So today, when you’re shutting it down and thinking you’ve done all you can for the day… ask yourself this one question, What is one more thing I can do right now?

There are a LOT of tools out there that sales teams use to speed up their day and close deals. And if you must know one thing about me (at least in the realm of tools I use) it'll have to be that I'm Calendly's #1 Fan Boy.

Out of all the things I use, my team is no stranger to my love for Calendly... I talk about it constantly. But, I'm always curious about new sales and partnership tools out there, so if you want to send me a better one, do it - I dare ya!

And if you need to be convinced, here’s an unsolicited list of why I love it…

1. Saves me time
The number of hours Calendly has saved me in my career is hundreds, if not thousands, at this point. The amount of pointless time I spent going back in forth with prospects, customers and internal stakeholders to find a time to work for everyone was mind-numbing before I started using Calendly. Now, being able to send my calendar to someone or even multiple people to schedule is an absolutely game changer.

2. Super easy to use
Calendly is wildly simple to set up. All you have to do is connect your email address, choose the meeting duration, set the schedule, turn the meeting “on” and then start sharing your Calendly link for people to schedule. So easy!

3. Integration and automation
This is for the Calendly pros. The next level is when you start automating tasks after someone schedules time with you on your Calendly link. The sky is the limit using their internal integrations or a tool like Zapier. At PSV, we have setup automations to send out follow up emails/texts, create new leads in our CRM in Notion, add people to marketing campaigns or send a notification in slack to alert team members.

Got a better calendar tool out there we should know about? Send us a message and let’s nerd out!

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This post is a part of our Deep Dive series where we give a behind the scenes look at what it’s really like building a great product with a small, passionate team. I’m Jason, Head of Design at Plain Sight Ventures, and resident design nerd. Feel free to reach out to me at jason@plainsightventures.co if you want to connect about design things or coffee or running or really just anything!

We know that our product Pano is incredibly powerful. Having a tailored snapshot of your customer in seconds empowers anyone and everyone within the organization — customer-facing or otherwise — to understand a customer’s needs in a flash, without having to dig across multiple apps. But in testing with our users, we found that not everyone in an org agrees on the relevancy of certain data. For customer success, important metrics might be NPS or CSAT scores, while an account manager may be more concerned with recent payments and subscription status. Relevant data for one role isn’t always relevant for the next.

So how do we ensure that the right data is being surfaced for the right roles? The answer lies in personalization. In this deep dive, we delve into why personalization matters, the challenges it presents, and the journey we undertook to create a personalized customer view experience for Pano that truly empowers users to get to know their customers in a matter of seconds.

Why a personalized dashboard?

Personalization isn't just a buzzword; it's a necessity in getting the right information as quickly as possible. Highly technical or not, we all appreciate tailored experiences from apps and services that resonate with our unique preferences and needs. However, achieving personalization at scale presents its own set of challenges. It requires striking a delicate balance between automation and customization, ensuring that users can easily navigate and interact with the customer view in Pano while enjoying a personalized experience and not experiencing doom…or as we call it, data overload.

Never start from scratch

There are great examples of incredible personalization design everywhere. And big teams at big companies have spent millions (billions?) building, testing, and iterating to discover what works best for customization settings. So when setting out to design Pano's personalized dashboard, we drew inspiration from some of the industry's finest: Apple, Asana, Notion, and others who use a modular approach in shaping their vision of a personalized experience. We aimed to capture the seamless navigation and user-centric design that these products are known for.

Stepping into our user's shoes

To truly understand what Pano users needed, we took a step back and put ourselves in their shoes. What's the simplest path to success for someone using Pano for the first time? Is the customization the most valuable feature, or is our assumption of relevant customer data a better quick-start? These questions guided our design process, ensuring that every element added served a purpose, removing complexity and confusion along the way.

We knew that alerts should remain at the top of the customer view — these highlights give our users immediate insight to any possible “need-to-know” items on their customer. Developing and maintaining this hierarchy lended itself to rapid iteration on the layout of the customer view, and helped us lay the foundation for easily moving, resizing, and swapping data points.

Pair-designing, pair-programming, pair-winning

Collaboration is the heartbeat of innovation. In the case of Pano's personalized customer view, it was co-designed with input from both design and development (aka me and Jeremy Clarke), balancing user experience and technical feasibility. Doing so allowed us to work hand-in-hand (not literally, but virtually?), pushing through roadblocks and enlightening both sides with restrictions or opportunities for delight. This is where the magic often happens — when you join forces and set aside the afternoon to push ahead.

When you’re building a solution with a small team and a “speed over perfection” mentality, iteration is key. We embraced this philosophy, designing screens and building same-day to gauge how the dashboard felt in practice. These quick iterations helped us identify pain points and opportunities for improvement. With each iteration, we inched closer to a customer view that seamlessly blended personalization, usability, and innovation, and allowed us to create a personalized experience for Pano that adapts and evolves as users engage with it, ensuring that the insights delivered are always relevant and insightful.

A Personalized Future Awaits

The journey of designing and building a personalized customer dashboard for Pano was a labor of love, guided by a commitment to enhancing the snapshot experience for our users and working towards a truly tailored customer view. Through user research, drawing inspiration from industry leaders, understanding user perspectives, and collaborative design, we've paved the way for a truly personalized future for Pano - where insights meet innovation, and customers' journeys are more enlightening than ever before.

To learn more about Pano, check out gopano.io. And stay tuned for more deep dives with the PSV team!

This post is a part of our Keep Your Head High series where we share advice on how to stay motivated through the inevitable ups and downs of startup life. I’m Gabe, head of partnerships and sales at Plain Sight Ventures, and your MC for this rodeo. Feel free to reach out to me at gabe@plainsightventures.co if you want to connect or need advice on how to keep pushing forward when things get tough.

Every day, I wake up and have to be the front-facing person for Plain Sight Ventures and our portfolio of projects. With that comes quite a bit of pressure to maintain a certain level of energy — not unlike most founders. And while it’s tempting to run from the moment your eyes open, I’ve learned this will really get you in the end. So that’s why each day I follow a super simple routine that helps keep my mind clear and my energy high.

And after having hundreds of conversations with successful entrepreneurs, founders, and salespeople, it seems I’m not alone in this. No matter what the business, the ones who sustain success know how to take care of themselves. They know that in order to stay sharp every day, they have to maintain their own wellbeing.

Now there is quite a lot that goes into my morning routine, but for today I wanted to share a few things that anyone can do:

1. Make my bed.

‍I snagged this one from Navy Seal Admiral William McRaven. I’m pretty sure 99% of what any Navy Seal does each day is a pipe dream for me, but this one… this one we can all do. While it may seem small, completing this one intentional act in the morning has a way of setting the course for the rest of my day. Plus there’s just no excuse not to…

”If you make your bed every morning, you will have accomplished the first task of the day. It will give you a small sense of pride, and it will encourage you to do another task and another and another. By the end of the day, that one task completed will have turned into many tasks completed. Making your bed will also reinforce that the little things in life matter. If you can’t do the little things right, you’ll never be able to do the big things right.

If by chance you have a miserable day, you’ll come home to a bed that is made - that you made - and a made bed gives you encouragement that tomorrow will be better. If you want to change the world, start off by making your bed.” — from Admiral McRaven’s University of Texas commencement speech

2. 10-minute meditation

‍Every morning, I do this 10 minutes to thrive meditation by Tony Robbins. It’s short and sweet. It’s easily achievable. Bookmark the YouTube video linked and have your headphones nearby to make it as easy as possible to do. This meditation has three steps that help me throughout the day:

- Pick three things that you are grateful for and focus on them for one minute each.

- Pick three things that you want to accomplish in your day & focus on them for one minute each.

- Focus on the abundance that you have in your life and then pick three people and imagine sharing your abundance with them.

3. Morning fuel‍

I start my metabolism as soon as I wake up in the morning by eating a high protein and fiber breakfast. This includes a protein shake, eggs, avocado and almonds. Much like the previous two activities, they’re quick and simple yet profoundly helpful in making sure I can stay focused throughout the day.

4. Sauna and cold plunge

‍This one may not be something you can do easily, but it has been life-changing in how I stay clear-headed every day. Every morning, I jump into a cold plunge (38 degrees) for one minute, then jump into an infrared sauna for 20 mins and then finish with a 3-minute cold plunge. This process is known to reduce inflammation, increase circulation , and provide numerous mental benefits.

5. Find your why

‍It would be so easy for me to wake up and not do any of these things. To put them off until the next day when I am feeling sluggish and tired. We’re all going to have those moments. But what cements all of this is tying it to a deeper vision of where I want to be and who I want to be. Thinking about my team at PSV and the people I care about helps — knowing that when I’m in a better headspace, the more I can support them. So don’t skip this one, it’s the most important.

We all have our own ways of getting motivated for the day — and these are surely nothing new — so tell me… what keeps you chugging along each day?

This post is a part of our Unexpected Sources of Inspiration series where we share how inspiration sometimes comes from the unlikeliest of places. I’m Jason, Head of Design at Plain Sight Ventures, and your friend in the design-nerd world. Feel free to reach out to me at jason@plainsightventures.co if you want to connect about design things or coffee or running or really just anything!

Design inspiration can, and often does, come from anywhere. It could be a magazine in a waiting room or a random consumer site or even a memorable meal. In a world of recycled Dribbble x Pinterest x AI shots, it’s refreshing when the inspiration somehow makes its way to you, rather than you going out and finding it. You cannot always force creativity — sometimes you just need to let it in. In this series, we will explore unexpected sources of inspiration through just getting out there and living.

You cannot always force creativity — sometimes you just need to let it in.

Travel is and has always been a major source of inspiration for me. Different colors, intriguing shapes, and unique characters become design muses that leave an indelible mark on your spirit and soul. By breaking away from your routine and exploring the unknown, you open yourself up to inspiration from afar and let the source right in. And as if by chance, a recent creative block aligned with a trip to one of my favorite places in the world: Japan.

Japan is not just a country…it’s a feeling, a sensibility, a vision of how things could operate, a glimpse into a world seemingly detached from the riggers and patterns of the West. It’s this sensory escape that leads to a creative awakening. The colors, shapes, textures, and lines you encounter are like nothing you've seen before. They spark a whole new level of design thinking that goes beyond the ordinary and piques your curiosity.

Colors in Japan often represent emotions and stories. Think of the striking red Torii gates against the calm backdrop of an emerald green rock garden. These bold and muted colors together tell tales of energy and serenity. Drawing from these hues, designers can add a touch of both modern energy and timeless elegance to their work, while grounding themselves in the basics of color complements.

Japan really has shapes figured out. They seem to blend nature's curves with precise geometry in just the most effortless ways. It’s the graceful lines of traditional woodblock prints alongside the sleek angles of Tokyo's modern architecture and the fusion of these organic and structured shapes that spark fresh design ideas.

Then there's the "wabi-sabi" philosophy that celebrates imperfection. Embracing this, designers can introduce asymmetrical shapes that add authenticity and a sense of life's fleeting beauty to their creations.

Written English characters might not always steal the show in western design, but Japan's calligraphy gives the written word new meaning. The intricate strokes of "kanji" characters and the fluidity of "hiragana" and "katakana" scripts are like a playground for typography lovers. Just like brushstrokes in calligraphy, each character choice carries its own meaning. The dance between bold and delicate, intricate and simple, creates a visual rhythm that speaks volumes. So, when you pick a stroke in Japan, you're not just picking letters – you're picking an emotion and a cultural connection.

Japan's design inspiration isn't just about individual elements. It's about bringing opposites together in harmony. With these elements in unison, a doorway opens to a world where tradition dances with modernity, and simplicity holds hands with sophistication.

In Japan, “ma” is the art of embracing the space between objects, leaving room for imagination. This principle encourages designers to be intentional with their compositions, creating a sense of balance. So maybe that’s the secret to all things…just making space for the unexpected.

By soaking in the unexpected beauty of Japan's design landscape, designers can reshape their creative approach. They can add that touch of balance, that dash of authenticity, and that spark of cultural connection that makes their work truly stand out – much like the captivating spirit of Japan itself.

Currently reading “Contagious: Why Things Catch On" by Jonah Berger which outlines six key principles, known as the STEPPS framework, that contribute to making information and ideas go viral.

1. Social Currency: People share things that make them look good, smart, or in-the-know to their peers. They use sharing as a way to enhance their own image or reputation. To make something contagious, it should provide social value and make sharers feel like insiders.
2. Triggers: Certain things trigger people to think about a product or idea. These triggers can be everyday occurrences or cultural references that make the concept top-of-mind. Making a product or idea connect with frequent triggers increases its chances of being shared.
3. Emotion: Emotions drive people to share. Content that elicits strong emotions like awe, excitement, anger, or joy tends to be more shareable. The more intense the emotion, the more likely people are to share it.
4. Public: People are more likely to imitate actions that are observable to others. Public visibility influences behavior, as people tend to imitate what they see others doing. Making the product or idea more public and visible can increase its contagiousness.
5. Practical Value: People share things that have practical value or help others solve problems. Information that is useful, informative, and can make a difference in people's lives is more likely to be shared.
6. Stories: People share stories because they're easy to remember and retell. Creating a narrative around the product or idea makes it more relatable and memorable, which increases the likelihood of it being shared.

What do you think? How are you using these principles to share your gift/product/service with the world?

Every couple days I go to the climbing gym. I like the solo nature of the sport. I like that I can just walk in and head straight for the wall. And at this point, I’ve gotten very clear about which routes I can do easily and the ones I need to work at. While there’s some critical thinking involved, most days I can just zone out and hop into a sort of flow state. That was until last Tuesday.

I went in like any other day, except it seemed like every single route I normally found to be a cakewalk, this time was such a struggle. I couldn’t get my feet in the right position. My hands were weak, and I couldn’t hold on as long. I got gassed more quickly. My entire rhythm was thrown.

Then two days later, it was like a switch went off, and I was back to my normal speed, my normal flow. The first try of the day — I climbed to the top with no problem. I wasn’t injured. I was sleeping well. Physically, even mentally, everything seemed the same.

While this is just one day at a rock climbing gym (aka low stakes, who cares), this sort of unpredictable nature is baked into every founder’s experience, including my own. One day you may feel like you’re able to grind like you always do, and then conceivably out of nowhere, the tank runs dry and you’re aching just to get to lunch.

It’s easy to get sucked in to these moments and over-analyze what was different. To spiral a bit about why one day wasn’t as strong as the next. Or to make some sort of deeper conclusion about your ability to do the work at all. But in the case of the rock wall, instead of quitting — or honestly worst, feeling defeated — I just pivoted. I went upstairs and worked on the training area to strengthen my hands. I did some cardio. I worked on small fundamental things that kept me in the flow.

Staying in the Flow

Me and my team at PSV are constantly talking about ways we can can stay in that flow. With all of us being in different cities, it’s much harder to find a rhythm together, but It’s one of our core tenants for a reason. Finding our flow keeps us in lockstep with each other and enables us to do great work together. It keeps us aligned and clear about the rhythm of our business and what we are building so that everyone is free to run at warp speed when they can, and pivot to those “training exercises” when they need to. And not everyone is going to be at the same level every day, so you have to make sure you have strategies that account for that.

This could look like co-working on a Zoom call together. It can look like splitting up a bigger project, or stripping it down to the nuts and bolts of what’s required. It can look like taking an evening off to rock climb and starting fresh early the next morning. Sometimes it’s about pivoting to a new task and other times it requires a complete reboot. As our team has gotten to know each other better, we’ve also learned who needs what and when. And we’ve seen the results of what it means to give someone permission to simplify or let go of the thing entirely.

My point is, staying in the flow successfully requires the clarity of mind to know when to redirect that river of work and when to shut it down. This is more of an intuitive call, so while I can’t tell you how to do that, I can share some things to keep in mind that help.

Here’s how to stay in the flow:

1. Split up your work into categories of tasks that range from tasks that don’t involve much thinking (but likely are more tedious) and tasks that require a bit more mental dexterity. Always have a list of things you can do in either and when one isn’t working, switch over to the other.
2. Pay attention to the nuances of your energy and your team’s. Not everyone is going to operate at full speed at the same times of day. Find when you work best and optimize for that. It may mean a bit of choreography to get things done as a team, but we’ve learned not everyone is going to have the same energy time blocks.
3. Somewhat related to #2 — create blocks of time in your day when you can 100% focus on getting things done. Close down the Slack notifications, don’t respond to emails. Just get things done.
4. Just start somewhere. If there is a bulky task that you keep putting off, find something in it that you can do in less than 30 minutes. Once you get the ball rolling, you’ll find the rest is much easier to tackle.

Staying in the flow is not always going to be easy. But having those training exercises you can fall back on is going to mean the difference between getting through and going home.