We’re excited to share a new 1st Team with Casey Rosengren: founder and executive coach. Casey is currently coaching through No Small Plans, an evidence-based coaching practice for founders & leaders in tech.

Prior to No Small Plans, Casey founded Hacker Paradise, worked at Xenon Partners (a SaaS-focused PE fund), and launched a number of community projects (ex. Recess Labs and Open Div).

Can you tell us a bit more about No Small Plans and what makes your practice unique?

No Small Plans is a coaching practice that uses evidence-based practices to help founders & execs manage their own psychology and become more effective in their work. 

Our approach is based on Acceptance and Commitment Therapy (ACT) — a modern framework that is backed by hundreds of randomly controlled trials. At a high-level, ACT helps people stay focused on their goals and connected to meaning, even when challenges arise. 

More concretely, when we undertake work that is important to us, we are likely to run into situations that bring up difficult thoughts and feelings. Over time, our work and lives can become more about avoiding pain & discomfort than about moving toward our values and our goals. 

Our coaching work is about helping leaders to stay aligned with what’s most important–even in stressful or challenging circumstances. 

For more about ACT and how we work, you can check out these pieces we wrote for Every:

• How to do Hard Things

• How to break the anxiety-fear-avoidance cycle

• Tactical Mindfulness

At what point does it generally make sense for a founder, executive, or individual to find a coach?

I’ve been skeptical about coaching since my time as a founder. That said, I think there are a few times when it clearly makes sense:

• When there is a specific skill you want to learn, it can make sense to hire an expert in that field to help get you up to speed (sales, growth, etc.)

• When you’ve got a lot on your plate, and could benefit from talking it through more frequently or more openly than you can with your friends / mentors

• When you’re falling into patterns that are below the level of performance you know you’re capable of – when you feel like you’re becoming the bottleneck in your business

There are many different types of coaches, and the value people derive from coaching ranges from accountability to working through emotional blockages to reconnecting with meaning after burnout. 

In general, I think folks become more effective with more support in their work and life. That said, it can be hard to find good support.

Do you have any recommendations on how one can go about finding a coach or framework that works best for them?

The first thing to get clear on is what you really want from coaching: if coaching were to succeed, what would be different in your life? 

Once you’re clear on that, there are three things I’d think about when meeting potential coaches:

1. Does this person speak my language?

2. Does this person know what they’re doing?

3. Do I enjoy talking to this person, and can I see us forming a meaningful helping relationship?

One of the big differences between coaching and therapy is that coaches come from industry. This shared context means that a lot can be left unsaid in-session. 

For example, as someone who has been in startups for over a decade, I tend to connect well with founders and VCs as clients. On the flipside, if someone comes to me looking for help in a more corporate environment, I’ll refer them to someone else. You want to find a coach who has walked a path similar to yours, or is at least familiar with the territory.

There also isn’t any real credentialing process for coaching, and many of the training programs out there for coaches are not that great. As a result, coaches vary widely in quality, and many work on intuition, with no real theoretical orientation to ground their work.

This isn’t necessarily a deal-breaker – there are some good intuitive coaches out there who are helpful, even if they can’t explain how or why. That said, I’d look for folks who have a deeper theoretical basis to their work and who are on top of the modern psychology and performance literature. 

A coach can be effective without these mental models, but in my experience, the best ones have both good intuition and a solid grasp of the research.

Finally, one of the biggest correlates of success in coaching is the quality of the relationship between client and coach. Thus, it’s important to find someone you trust and who you feel good about sharing vulnerably with on a regular basis.

What led you to start No Small Plans?

After college, I bootstrapped a company to an exit. While we had a good outcome, I was stressed out and unhappy a lot of the time while running the company. I couldn't see myself doing anything other than entrepreneurship with my life, and yet I didn’t know how I could be happy starting another company.

So, I spent a lot of time digging through psychology research to try and understand my experience and figure out how to be an entrepreneur and also feel like I’m living damn well. When I found something that worked for me (ACT), I realized it could also help a lot of other people, so I began training with several psychologists in how to adapt this particular framework to startup life.

What sort of clients do you work with at No Small Plans?

I typically work with founders and executives of Seed and Series A companies who are looking to manage stress, improve their decision-making, and find more meaning in their work. I also coach a few VCs and university professors.

In particular, I like to work with folks who are exploring what it means to live well while running a company – or as one of my clients put it, “I want work to be a significant part of my life, but I also want LIFE to be a significant part of my life.”

What is the best way to inquire about working together?

Happy to offer a free intro session to VCs / founders from the SandHill.io network. You can find out more at nosmallplans.io, or shoot me an email at casey@nosmallplans.io.

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Led by a team of Stanford, Apple, and Paypal alumni, Tintash is a software development firm that offers clients managed remote engineering teams from around the globe. They design and build digital products from scratch and can also augment existing engineering teams

The company has grown to over 200 employees and has worked with a notable roster of clients across industries, including sports betting giant DraftKings, mobile game developer Stick Sports, blockchain company Stacks, Bed Bath and Beyond, and dozens of others. The firm’s clientele range from startups at the earliest stages to Unicorns and Fortune 500 companies.

In this post, Faizan Rasool, VP of Marketing & Sales at Tintash, shares tactical best practices for finding, vetting, and working with overseas development partners. A special thanks to Mannan Amin and Aiza Yasir for their assistance with this post.

Tintash is one of the firms that came highly recommended by founders through our 1st Team survey. If you’re looking for an engineering partner, fill out the form through the link below and let them know you heard about them from SandHill.io!

Get in touch with Tintash

1 – What materials or research would you recommend a startup pull before engaging with a development partner?

The answer will depend on what stage the startup is at. We see 5 stages during a startup's journey: Discovery, Investor MVP, Goto Market MVP, Improving Product-Market Fit, and Long Term Growth (also shown in the table below).

If you are a startup in the earlier stages then you should start by answering some questions to get started on early customer validation which will also help with the prioritization of your MVP feature set. These include:

1. Who is the customer of my product? Try to clearly define an ideal customer archetype here. 

2. What specific problem do I want the product to solve?

3. What is the core experience my customer needs to solve their problem?

4. Are there any competitors in the market that are already doing this? What are their most used features? Any pain points in those key features?

5. When do I want to release my product? Why is this timeline vital for me?

We’ve seen founders come to us to kick-start product development but they haven’t given thought to some of the above questions. This can lead to a delayed kick-off and can create roadblocks during product development. 

At the same time, it is important to understand that you can’t have complete clarity in the earlier stages. You will get there iteratively by building and testing MVPs. However, at least going over these questions and writing down assumptions saves time getting the design and engineering team on board toward the vision of your product.

We’d also recommend understanding what is important to potential investors. This will help guide the building of an investor MVP (what we like to call the MVP at this stage) to test early customer validation.

In later stages, it is more about understanding that improving product market fit is a journey. To begin with we recommend the superhuman product market fit approach to have a way to measure progress and to figure out which features you’re going to prioritize in the next iteration(s). 

For non-technical founders, it really helps to have a technical advisor or friend to help build trust with the engineering team you choose. For example, they can help validate at the ballpark level scope-time required, which helps build confidence / trust with the tech team. 

Usually closer to the growth stage the team has decided on tech stacks, project management tools, work times, and culture which help select the right engineers to augment the team with. 

In terms of books and materials we highly recommend:

• The quick talk on systems thinking TED talk by Tom Wujec, 

• The superhuman product market fit article. 

• The book, “Don’t Make Me Think” by Steve Krug

2 – What is your general recommendation to startups on whether to go with a fixed cost or flexible cost arrangement when working with an overseas development partner? Does it vary for startups vs. corporates?

We feel the overseas part should not change the best approach required to set up your startup for success. Fixed cost is generally not the way to go since it implies fixed scope/features which hurts because the nature of a startup requires evolution on what is to be built the minute you have a better understanding of it with market interaction. Additionally, startups have engineering unknowns on the product roadmap. If these unknowns aren’t there then a fixed cost model may work. However, with any unknowns, the development team will be taking a risk with a fixed cost commitment. 

However, we do understand that funds are always limited. The approach we recommend is to have a clear set of priorities for what is to be built/improved and tested in the next iteration(s). Then see if the partner team can commit to building it all within the given funds. If not, then you must further reduce the scope. Often engineers may be solving things in certain detail which is not required for the early validation phases a founding team is looking for to get the next round of funding. 

Even for larger companies, budgets for projects have limits and hence should follow a similar line of thinking. Else you risk building something that may not be a requirement of the next stage of market interaction/testing. 

Thus, overall our recommendation is to think about what are the biggest (un)knowns that can have the biggest impact on the success of the product and build those to test out the market.. 

Another way to think about fixed vs flexible is what risk you are trying to reduce. Do you only want something built within a certain budget or do you want the right set of incremental features to be tested in iterations given your runway. A team working with fixed costs for a scope will be stressed to complete your project and move on to the next one. They will not be motivated to spend the time with you to understand what are the most important elements to build or tweak to test next.   

3 – What are some common challenges that arise when working with startup clients? Any advice on how to manage these challenges?

There are many challenges that arise. I’ll share the three main ones:

The biggest challenge is managing expectations with founders. The reason is planning fallacies that somehow become an inherent part of founder expectations. We’ve learned the hard way that we need to help founders plan for not only the best case and worst case scenario but also to expect that the initial iterations will land you somewhere in between.

The reality is that turning a startup into a success requires several pivots and iterations before a product-market fit is achieved, and even after product-market fit is achieved, the journey towards a growing business requires making numerous other adjustments. 

Planning fallacies are best described by the Nobel Prize winning author Daniel Kahneman in his book “Thinking Fast and Slow”. He talks about how those who are executing an idea can indulge in delusional optimism and assume that only the best case scenarios will play out in the execution of their project, rely too much on their own calculations of how much time and effort it can take to execute something, and can ignore the outside view of experts on the time, effort and cost other similar projects have incurred in the past.

The second one is not having a clear understanding of the product vision, its core functionality, and what problem they’re trying to solve for their customer. This requires spending time in discovery where we can help unravel different use cases, create visual references, get an idea about technical unknowns, and overall lock the initial scope of the product. 

Third, not considering the product/development team, their team. You know the popular saying that “culture eats strategy for breakfast”. Startups need a highly engaged team culture. 

Founders must take time to not only share their big vision with the development team but also explain why and how the next iteration/problem they are going to solve will have a big impact. The team will usually respond by taking a lot of ownership and everyone is surprised by the magic that happens.

4 – It sounds like, in addition to development, Tintash often helps clients with other aspects of product strategy as well. What do some of these other processes, such as Discovery, look like?

The goal always is to enable our client to be successful in evolving to the next stage in their product evolution and overall startup journey.

As mentioned earlier, if a customer is very early in their journey, then we start the engagement with a Product Discovery stage. This helps define product goals, understand the customer archetype(s), map out user journeys, create low-fidelity wireframes, define a brand language and incorporate that into polished mockups. Additionally, we are able to run tech due diligence, identify unknowns, and figure out an engineering scope plus ballpark estimates. 

In the scenario where a customer comes to us at a stage where they already have the development requirements sorted out, we still do a due diligence exercise with them. This helps to ensure that we as a development partner have a strong sense of who the end-users are for our customers, what value proposition our customer wants to bring to the customers through the product they’d like us to build, and how the requirements they’ve already gathered will enable their product to deliver intended value to their customers once developed. We do this exercise to enable the assigned team to understand the why behind what needs to be built. In almost all cases, this due diligence exercise helps in further refining the requirements, which helps ensure that we use the precious runway available in the best possible way.

5 – Startups are often under pressure with the limited runway. Any recommendations on how best to work with a development partner, especially in a flexible arrangement, when your runway is constrained?

It is imperative to ensure that every bit of runway is used in the most effective way possible. This requires that everyone involved in the project should consider themselves to be a part of the same team. When it comes to delivering a product with limited runway, there is no space for an ‘us vs them’ mentality. Our leadership team is regularly working with our customers and their teams at Tintash (we refer to them by the customer name) to make sure that this cohesion exists on all of our projects.

Coming together as a single unit enables everyone to get onboard and have a common understanding on the overall product goals, the available timelines and budget in which they need to be delivered, the milestones/work increments that need to be achieved, and the quality at which they need to be delivered. This of course requires transparent and consistent communication on the above mentioned aspects. 

We’ve been able to effectively use a modified version of the scrum model to ensure that the work process retains the agility a startup needs to respond to quickly changing scenarios while making sure that there is a tight handle on scope and budget. There are two main aspects to this model that we follow. Firstly, there should be a defined work cycle/sprint, and then second, the milestone/work increment should be delivered. The scope of the work increment is decided at the start of the work cycle through a sprint planning meeting, and then the work increment is delivered at the end of the cycle through a sprint end meeting. Sometimes the two meetings are combined into one. The goal is to ensure that usable software is tested and delivered regularly. The teams also meet on a daily basis to regularly review progress across the work cycle. 

Additionally, the leadership within the team needs to come together every two weeks or four weeks, to evaluate what product goals have been achieved and what budget has been spent to keep a tight handle on budget and scope.

6 – Do you have any advice or tips for how a startup should go about finding and evaluating an overseas development partner?

There are two parts to this: Finding the partner and Vetting them.

For finding, look for referrals from your network, and go through listings like Clutch.co (such listings are sometimes sponsored so sift through carefully). We recommend talking to a few companies to get a sense of the landscape.

For vetting, go through their sites, decks, and where possible try out some of the applications they have worked on recently. 

Next, talk to the team that will be assigned to your project. All teams are not equal in any company (we believe!). If you're not technical, have a tech expert friend talk to them and rate them on the required skill sets. 

And lastly, we actually recommend prototyping the relationship with the development team. Carve out something small and work with them. See if they can prove the tech abilities needed and are a good work-culture match for you. No team will be a complete match in the beginning but each early sprint should get better in terms of communication and delivery. 

7 – What is the best way for a potential client to inquire about working together?

What a great question! Ping us on our contact us page on our website and do mention that you read about us in this article. It’s a simple, short form that takes a minute to fill out. Our customer success team will follow up shortly!

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When I was in VC, one of the resources that we built for our portfolio was a list of agencies & service providers that came highly recommended from other operators & investors. The intention was to have a list of providers that our portfolio founders could leverage as they built and scaled their companies.

A few months back, I asked our subscribers who the top vendors are that they have worked with, receiving close to 50 responses from founders and VCs. The result is an incredible list of providers from across the globe ranging in offerings from SEO, PR, and growth to recruiting, development, and more. In the coming months, we’ll be highlighting many of these providers and sharing insights they’ve learned working with early-stage companies.

We’re kicking off this new 1st Team series today with Tintash. Led by a team of Stanford, Apple, and Paypal alumni, Tintash is a software development firm that offers managed remote engineering teams from around the globe. They design and build digital products from scratch and can also augment existing engineering teams.

We dove in with Tintash on best practices for finding and vetting an overseas dev partner, how to structure contracts to align incentives, and the best ways to manage these engagements to get the results startups need. Check it out here:

The Tactical Guide on Finding & Working with
Development Partners Overseas →

If you’re a VC-backed founder or investor that has worked with an agency or service provider that you would highly recommend, please let us know (team@sandhill.io)