Anatomy of a Win-Win Acquisition: Synergy, Growth, AI, and the Future of SaaS | E2047

Spenser Skates of Amplitude & James Evans of CommandAI join Alex. (0s)

• Private equity firms make significant amounts of money and are great players in modern capitalism, but one should never be on the other side of a transaction with them as they have strategies to take away surplus during the transaction (10s).
• Private equity firms often use playbooks that involve consolidating market share to create monopolies or pseudo-monopolies and raising prices on consumers (32s).
• The US antitrust legislation tests for anti-competitive behavior by checking if prices go up or down for consumers, and private equity firms' playbooks often lead to price increases (42s).
• There is a suggestion that the FTC should regulate private equity firms more strictly, and the next administration should take action against them (53s).
• The discussion is sponsored by Squarespace, Gusto, and Dev Squad, which offer services such as website creation, payroll and HR management, and product development (58s).
• The host, Alex, welcomes everyone to the discussion (1m39s).

Startup M&A trends and Amplitude's acquisition of Command AI (1m40s)

• Startup M&A activity has decreased significantly since 2021, with overall exit volume for US startups collapsing, making notable deals more interesting to discuss (1m42s).
• Amplitude, a public unicorn, acquired Command AI, a startup that raised $24 million in known capital, including a $19 million Series A in mid-2022, valuing the company at $123 million post-money (2m33s).
• Command AI is a user assistance software company that aims to make the internet easier to use, and its founders, James Evans and Spencer Skates, were invited to discuss the acquisition (2m35s).
• The deal was done between Amplitude, a former startup that went public in 2021, and Command AI, which raised capital from investors, with the acquisition providing an opportunity to learn about the process and what founders can learn from it (2m38s).
• James Evans, CEO and co-founder of Command AI, has a background in private equity at Bain Capital, where he was exposed to poor software, leading him to start Command AI to address the issue (3m46s).
• The acquisition of Command AI by Amplitude is seen as an interesting deal, with the opportunity to discuss the process and what founders can learn from it, as well as the potential for growth and synergy between the two companies (2m31s).

Overview of Command AI's user assistance technology (4m30s)

• Command AI's user assistance technology aims to solve the problem of usability challenges in software, where users often struggle to find what they need to do and may have to read help center articles or deal with annoying pop-ups (4m31s).
• The company's technology is designed to provide a better user experience, unlike other software companies that offer nudges or user assistance that can be annoying and often closed by users (4m58s).
• Command AI's product is a no-code platform that allows marketers, product managers, and customer support teams to build user experiences without needing to bother engineering teams (6m20s).
• The platform includes a dashboard where customers can instrument experiences, such as nudges or chatbot interactions, and a user flow feature that allows users to reward users for completing certain actions (6m9s).
• The user flow feature can be used to show users a GIF and a "what else can I do" button after completing a milestone, providing a sense of accomplishment and suggesting a next best action (6m52s).
• The goal of Command AI's technology is to create a more seamless and user-friendly experience, and the company will demonstrate its product to showcase its capabilities (5m38s).

Integration and benefits of Command AI within Amplitude (7m5s)

• Amplitude recently launched "Amplitude Made Easy," aiming to make the platform more user-friendly for low-code and no-code individuals, but the company acknowledges that creating native-feeling interfaces is not their expertise, which is part of why they acquired Command AI (7m21s).
• Command AI's user interface is designed to be clean and well-defined, which is a crucial aspect of their product, as they help other companies create user-friendly software (7m50s).
• Command AI offers features beyond nudges and gifts, including a survey component, and their product can be integrated into various applications to provide a better user experience (8m11s).
• The company has developed a sample app, a calendar-to-do list app, to demonstrate Command AI's capabilities, showcasing how the product can help users navigate and find what they need (8m27s).
• One of Command AI's most popular features is the "nudge" system, which intercepts user confusion by tracking mouse movements and providing helpful messages to guide the user (9m3s).
• The nudge system is designed to present users with relevant options based on their behavior and interests, and it only appears when the user is likely to be lost or confused (9m17s).
• Command AI emphasizes the importance of timing when showing messages to users, avoiding interruptions and pop-ups at inopportune moments, and instead using triggers like confusion detection to provide a better user experience (10m7s).

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• Every startup needs a professional-looking website, but creating one can be time-consuming, which is why Squarespace is a great option as it saves time and effort (10m27s).
• Squarespace has a new AI-powered design intelligence tool that helps users build unique and fast websites (10m49s).
• The platform also features an e-commerce engine with built-in payment technology, making it easy to start selling products online and generating revenue (10m55s).
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• Squarespace is a highly endorsed product that has been a long-running supporter of This Week in Startups (11m37s).

Enhancements in user surveys and feedback with Command AI (11m45s)

• A micro survey approach is encouraged, where short surveys are constantly shown to users to get their pulse and feelings about what they're seeing, and this information can be used for targeting purposes (12m10s).
• Using a rating input, such as a star rating, can be an effective way to get user feedback and can be used to personalize the user experience (12m30s).
• Intercepting users at the right time and context with personalized messages can be five to 10 times more engaging than spamming them with generic messages (12m55s).
• Personalized messages can turn a negative experience into a positive one, rather than just going from zero to five, it's going from negative five to five (13m23s).
• Measuring the rate at which users close popups, also known as "rage close," is important, as it can indicate if the message is annoying or not personalized (13m45s).
• If a user rage closes three popups in a row, they may develop "popup blindness" and never engage with the product again (14m17s).
• Differentiating between users who didn't engage with a message and those who actively hated it is crucial to avoid losing them forever (14m27s).
• A product called "Nudges" focuses on proactive messaging, getting in front of the user before they know what they're trying to do (14m37s).
• Another product called "Co-pilot" is an AI-powered user assistant that utilizes information about the product to assist users (14m43s).
• Co-pilot can be used to create a personalized experience for users, such as providing help center information (15m4s).
• A unique approach to chat interfaces is being implemented, where instead of treating them as a fallback, they are used as a query-first way of helping users, and often teaching them how to use the underlying product. (15m5s)
• This approach involves guiding users through the interface, pointing out where they can perform tasks, and taking them to the next step in a multi-step flow, making the chatbot form factor more useful. (15m39s)
• The goal is to avoid sending users to help center articles that they don't need to read, only to have to relog back into the application, and instead provide a more seamless and guided experience. (16m0s)
• The use of AI in this approach is not just about providing a wall of text, but about providing a guided and interactive experience that feels authentic and valuable to the user. (16m40s)
• The vision for this approach, led by James and Ben, is what excited Amplitude to work with them, and is seen as a magical use of AI for end users. (16m50s)
• The approach is also seen as a way to banish the common experience of being sent to FAQs that may not answer the user's question, and instead provide a more personalized and helpful experience. (16m9s)
• The use of AI in this way is not about replacing human interaction, but about providing a more efficient and effective way of helping users, while still maintaining the authenticity and value of human interaction. (16m29s)

Amplitude's strategic vision behind acquiring Command AI (16m58s)

• Amplitude is primarily known for its digital analytics with a product focus, which is a fair description of the company (17m2s).
• Amplitude's customers are looking for consolidated solutions, indicating that point solutions are becoming harder to sell, which is why the company decided to acquire Command AI instead of building a similar product in-house (17m17s).
• The founders of Command AI, James and Vannan, have an incredible amount of expertise in their field, having worked on the problem for four years, which is beyond the expertise of anyone at Amplitude (17m39s).
• Amplitude decided to acquire Command AI to partner with the team and bring their combined expertise to market quicker, with an aggressive internal goal to release the product to customers within 90 days of the transaction closing (18m8s).
• The acquisition was announced on October 15, and Amplitude aims to release the product to its customer base shortly after, leveraging the combined expertise of both companies (18m22s).
• The approach to building modern enterprise software is shifting, with a greater emphasis on user experience and crafting products that are simple, usable, and provide amazing end-to-end experiences (18m55s).
• Companies like Data Dog and GitLab have successfully prioritized user experience, winning in the market due to their ability to make complex software simpler and more usable (19m13s).
• Amplitude has been intentional about prioritizing user experience, with a strategic pillar called "Win Simple" that aims to make analytics more accessible to non-technical users (19m46s).
• Amplitude has added features like session replay and Amplify to make analytics more accessible, and the acquisition of Command AI is part of this effort to provide a more comprehensive and user-friendly product (20m13s).

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• Over 300,000 businesses trust Gusto today, and it can grow with a startup as it scales (20m37s).
• Gusto handles state and federal taxes for staff across the country (20m46s).
• The company also offers 401k plans for teams (20m52s).
• Gusto helps employers with compliance, with three out of four saying it aids in government compliance (21m0s).
• Gusto is simple and easy to use, allowing businesses to focus on building their startup (21m7s).
• Gusto offers its services with no hidden fees, and new users can get three months free by visiting gusto.com/twist (21m20s).

Product-led growth and enhancing user experience at Amplitude (21m28s)

• Product-led growth is a concept that has lost favor in the market, but companies like GitLab, Datadog, and Upspot have successfully driven growth through this approach, making it easier for users to sign up and expand their footprint (21m33s).
• The digital analytics world is in the middle of a transition from Generation 1.0 of SaaS, where sales teams were more important than product experience, to Generation 2.0, where product experience matters a lot (22m16s).
• In Generation 2.0 of SaaS, companies need to combine a great user experience with a high-quality sales team, rather than relying solely on one approach (23m30s).
• The idea that a big sales team is the only way to succeed in SaaS is no longer true, and companies need to adopt a blended approach that includes product-led growth and high-quality software (23m37s).
• SaaS has become harder in the last couple of years due to increased expectations and pricing pressures, making it more challenging for companies to succeed (23m49s).
• The decision to sell a company should be based on value and what is best for the team and investors, rather than the idea that selling out is a sign of weakness (24m44s).
• Command AI was not out of cash or struggling when it considered selling, but rather looked at the value and potential benefits of being part of another company (25m7s).
• The company's decision to sell was based on the potential to achieve its goals more quickly and effectively as part of another company, rather than as a standalone entity (25m39s).
• The founder's existential concern was that building a standalone company might not be the best way to achieve the company's goals and create value for customers (25m46s).

Amplitude's approach to scaling through strategic acquisitions (26m8s)

• Amplitude's approach to scaling through strategic acquisitions involves finding a natural strategic fit, such as their acquisition of Command AI, which allows them to sell to their 3,500 paying customers and future customers, aligning with the physics of their business (26m8s).
• The acquisition of Command AI helps Amplitude crack distribution and get their product into the hands of more customers, as building a great product is not enough without effective distribution (26m29s).
• The physics of Amplitude's business aligns naturally with Command AI, as customers use Amplitude to figure out what's not working in their product or customer base, and then use Command AI to fix those issues (26m51s).
• Command AI helps finish the feedback loop started in Amplitude by allowing customers to immediately fix issues they've discovered, creating a natural tieout between the two companies (27m28s).
• Amplitude's customers use their product to track what people do and how they do it, and then use Command AI to apply tools to help unstick people or provide more value, creating a more liquid layer for experimentation and personalization (27m39s).
• Amplitude focused on being the best in-class in digital analytics and only recently branched out to experimentation and session replay, making the acquisition of Command AI a strategic decision to partner with a talented team rather than trying to build a similar product themselves (28m32s).
• The acquisition was a strategic decision to stay focused on Amplitude's core business and partner with a team that had expertise in areas they didn't, such as creating natural and in-context interfaces for nudges and guides (28m50s).
• Acquisitions are incredibly risky, with 90% of them failing, but the acquisition of Command AI felt relatively natural due to the alignment of the two companies and the demand from Amplitude's customers for a more comprehensive platform (29m37s).
• Amplitude's customers were asking for a solution like Command AI, and the acquisition provided a natural fit for their business, allowing them to offer a more comprehensive platform to their customers (29m55s).

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Managing acquisition risks, integration, and cultural alignment (31m30s)

• The acquisition of Command AI by Amplitude was not seen as extremely risky due to the alignment of their visions and the potential benefits of combining their expertise and products (31m30s).
• The main risks associated with the acquisition include overpaying and lack of integration, which can result in significant overhead costs and effort required for change on both sides (31m47s).
• Amplitude strongly believes in creating a world where products are no longer frustrating and technology adapts to the user's brain, and they wanted to partner with Command AI, who shared this vision (32m9s).
• The acquisition was not just about acquiring a fantastic product and expertise, but also about aligning with a team that shared the same view of how great software should be built (32m45s).
• One of the biggest mistakes companies make in acquisitions is not being clear about the end state they are working towards, and Amplitude was clear from the start that they wanted to create one platform together (33m0s).
• Leaving a company to run standalone while integrating it can be the worst of all worlds, and Amplitude was deliberate in communicating that they wanted to rebuild Command AI as part of one platform (33m16s).
• James, the founder of Command AI, knew that joining Amplitude's company and culture was a risk, but he got comfortable with the decision after spending time with Spencer and finding alignment in product and strategy perspectives, as well as cultural values (33m51s).
• Amplitude and Command AI shared overlapping values, including ownership and growth mindset, which made the integration easier (35m1s).
• The idea of going from a partnership to a transaction was not explicitly stated as being initiated by one person, but it was a mutual decision that arose from their discussions (35m14s).

Acquisition discussions and deal negotiation (35m19s)

• The acquisition discussions between Amplitude and Command AI started with a LinkedIn DM from Spencer, and the initial signal for a potential acquisition was the respect from Amplitude's product side for Command AI's work and the overlap of customers (35m20s).
• Command AI was growing rapidly, with a 3x year-on-year growth rate in the first half of 2024, which is considered fast even for a Series A startup (35m58s).
• The founders of Command AI had to get their investors comfortable with the transaction terms and taking an exit, which was a challenging and high-stakes conversation, but ultimately, the investors were supportive and helped reason through the decision (36m13s).
• The investors' vibe was to help the founders make the decision, and they trusted the founders' judgment, making the conversation well-reasoned and non-emotional (37m27s).
• Command AI was in the middle of a fundraising process and was in good shape to build a successful standalone SaaS business, but the founders saw the vision of what could be combined with Amplitude (38m3s).
• The negotiation process took quite a bit of back and forth to figure out how to create a construct that would make the equity of the two companies combined more valuable than separately (38m21s).
• James, the founder of Command AI, is credited with navigating and handling the conversation well, and the approach was to have a clear and open conversation about what they cared about and what would make the deal interesting (38m57s).
• The timeline from the first LinkedIn DM to the deal being closed is not explicitly stated, but the first conversation was mentioned, and the process involved multiple negotiations and discussions (39m30s).

Acquisition deal structure and stakeholder conviction (39m48s)

• Acquisition discussions between Amplitude and Command started in late spring or early summer, around April or May, initially as an exploratory conversation about a potential partnership or deeper product integration, but didn't focus on making an acquisition happen until the middle of the summer (39m49s).
• Amplitude's new CFO stated that the company is not a "growth at all cost" company, instead investing to drive accelerating growth while generating positive free cash flow, and making decisions on leverage (40m15s).
• The acquisition of Command was likely not cheap due to its fast growth, but Amplitude needed to make it worthwhile for Command to do the deal (40m36s).
• Amplitude's board of directors, who had experience with transactions, provided guidance and were supportive of the acquisition due to the conviction of the team that the combination was valuable for Amplitude and its customers (41m2s).
• The team put together a case for the acquisition, highlighting its potential value and the demand from customers, which helped gain the board's support (41m30s).
• Regulatory concerns and antitrust issues were not a major concern in the acquisition discussions, despite being a public company (42m3s).

Addressing regulatory concerns and valuation mismatches in acquisitions (42m8s)

• The acquisition of smaller companies may not be on the radar of regulatory bodies like the FTC, but they are cracking down on larger companies and transactions (42m9s).
• Not all companies building software will go public, and some may be acquired, but the complaint about regulatory concerns does not match the reality of the transaction discussed (42m30s).
• The market for digital analytics, nudges, and assistance is still early, and it will be many years before regulatory concerns arise (43m1s).
• The reason acquisitions like this don't happen often is due to a mismatch in valuations between public and private companies (43m12s).
• Public companies or recently public companies have lower valuation multiples, such as 2-4x ARR, compared to private markets, which can have multiples of 10-20x ARR or more (43m22s).
• This valuation mismatch creates a higher hurdle for larger companies to acquire private companies, as they need to have conviction that the combined value will be significantly higher (43m59s).
• To clear this hurdle, the combined value of the companies needs to be significantly higher, such as 5-10 times more valuable together than separately (44m14s).

Decision-making: Raising funds vs. selling a company (44m20s)

• Command AI could have raised more funds due to the excitement surrounding AI companies, but the decision to sell the company was not solely based on valuation, as the comparison between raising funds and selling is not always straightforward (44m21s).
• Founders often simplify the decision between raising funds at a higher valuation and selling the company for less, but this comparison does not account for various factors, such as growth rate and path to IPO (44m40s).
• In some cases, selling the company for less than its valuation might be a better option, especially if the combined entity can increase its value threefold, providing more upside for the founders and existing team (45m20s).
• The deal between Command AI and Amplitude was done mostly in Amplitude equity, with a small amount in cash for some existing investors, allowing James and the existing team to share in the combined upside (45m41s).
• The decision to use equity instead of cash was made to ensure that the existing team participates in the combined upside, aligning their interests with those of the new entity (45m51s).

Post-acquisition: Integrating Command AI's technology (46m0s)

• There seems to be a tension between the importance of offering a platform with multiple products and the success of point solutions, such as Command AI, which was growing at a rate of 3x independently (46m1s).
• The reason for integrating Command AI into Amplitude's platform is that the growth rate can be accelerated by leveraging Amplitude's large customer base, potentially growing 20x or 30x instead of 3x (47m12s).
• The goal is to get Command AI's software into Amplitude's customer base, with an estimated 10% adoption rate in the first year, and eventually reaching 50% or 100% (47m55s).
• The idea is that the bundled products make sense collectively due to platform, single buyer, and discounted pricing, and that Command AI's product is not being made worse to fit into a bundle (48m24s).
• The product remains the same but is now more easily accessible and integrated within Amplitude, making it more competitive (48m45s).
• The acquisition of Command AI makes sense because it brings standalone differentiation, and this is one of the reasons why buying can be more attractive than building (49m5s).
• Amplitude's CEO is open to doing more acquisitions in the future, but the attractiveness of doing so depends on various factors, including the market and prices (49m21s).

Amplitude's future growth strategy and leadership (49m37s)

• Amplitude's future growth strategy involves both partnering with other companies and building more internally, as the company believes that great companies can do both. (49m37s)
• The company is still in the early days of innovation in its space, and there are many adjacent spaces that make sense with digital analytics and the platform, making it likely that Amplitude will be doing more acquisitions in the future. (49m56s)
• One of the things that made the acquisition of Command AI exciting was the opportunity to work with great leaders, James and Benet, who are not just founders but also great product and engineering leaders. (50m57s)
• Amplitude is always behind on great leadership as it grows in scale, and the ability to work with leaders like James and Benet is important for the company's future growth. (50m38s)
• The company's CEO is comfortable with having distributed leadership and is looking for fantastic leaders who can partner with him in critical path details, rather than just delegating tasks or micromanaging. (51m42s)
• The CEO's approach is to be in the details of what is critical path for the company, such as product experience and sales, and to partner with leaders who can help achieve great outcomes in those areas. (52m44s)
• The CEO's goal is to have leaders at Amplitude who can have a peer-to-peer interaction with him, discussing and debating ideas to achieve great outcomes, rather than just following orders. (53m15s)
• The CEO's approach is not about delegation or micromanagement, but about partnering with leaders to achieve great outcomes, and he believes that this approach is critical for the company's success. (53m37s)

Transition from founder mode to distributed leadership (54m0s)

• Founder mode involves being heavily involved in the details of the company, working closely with peers, and not delegating important tasks, which is different from abstract leadership that can disempower employees (54m1s).
• Abstract leadership, as seen in companies like Boeing, can lead to disempowerment of engineers and employees, whereas founder mode encourages collaboration and empowerment (54m20s).
• Private equity firms make significant amounts of money but have a reputation for taking away surplus value during transactions, making it essential to be cautious when dealing with them (54m38s).
• One of the rules is to never be on the other side of a transaction with private equity, as they have a spreadsheet to maximize their gains and minimize the surplus value for the other party (54m45s).
• Private equity firms often follow a playbook that involves consolidating market share, creating monopolies, and raising prices for consumers, which can be considered anti-competitive (55m26s).
• The US antitrust legislation tests for anti-competitive behavior by looking at whether prices go up or down for consumers, and private equity firms often fail this test (55m35s).
• There is a need for regulation of private equity firms, and the FTC should take action to prevent anti-competitive behavior (55m18s).
• The discussion took a detour but aimed to bring the focus back to Spencer and his near-term goals and focus at Amplitude (56m7s).

Role of AI in Amplitude's product development (56m15s)

• Amplitude is currently working on two main projects: automated insights, which proactively surface information to customers without human intervention, and automated actions, where Amplitude recommends and takes actions to improve the end customer experience (56m15s).
• Automated insights seem to be related to digital analytics, while automated actions resemble AI agents, which have been gaining attention in the industry (56m35s).
• The goal is to create a future where software can automatically create custom guides for each user, providing a personalized experience (57m15s).
• This vision goes beyond just guides, aiming to enable AI to recommend and take actions that improve the end experience, such as suggesting different text or images on a website to increase conversion rates or resonate with users (57m41s).
• Amplitude is excited about the potential of AI to recommend changes to website layouts, break down functionality, and create new features (58m5s).
• The ultimate vision is to create a world where products are self-improving, always adapting to user behavior and preferences (58m13s).
• Amplitude's enormous repository of customer behavior data, one of the largest in the world, will play a crucial role in achieving this vision (58m25s).
• Amplitude plans to leverage existing AI models, rather than building their own, and focus on applying these models to their specific use case (59m8s).
• The company will use off-the-shelf AI technology, choosing between closed-source models (e.g., Open AI) and open-source models (e.g., Meta LLaMA) (59m34s).

AI model considerations and financial sustainability in B2B software (59m44s)

• Amplitude is using open AI models but is agnostic and can use open source models as well (59m45s).
• Open AI is currently losing money on every transaction, which is unusual for a business (1h0m0s).
• The gross margin is negative for Open AI, making it a challenging spot for the company (1h0m21s).
• Many AI businesses have poor retention characteristics, making their current model unsustainable (1h0m31s).
• The SaaS business model is still considered the best, despite taking a hit, due to its long-term potential (1h0m52s).
• The statement that SaaS is the best business model is contrarian in late 2024, but it remains a viable option (1h1m3s).
• The macro environment for B2B software is still choppy, with high buyer scrutiny, but the state of the B2B software buyer is improving (1h1m25s).
• The majority of overbought optimization contracts have gone through, but the market is still adjusting (1h1m15s).
• Sam Altman, the CEO of Open AI, is mentioned as someone who is losing money on every transaction, but the speaker has only met him once (59m57s).

Market position and growth of Command AI (1h1m34s)

• The software buying landscape has changed, with companies now seeking a return on investment (ROI) for their software purchases and wanting to ensure that the software addresses their top priorities (1h1m34s).
• As a result, companies are more scrutinizing in their software buying decisions, which makes Command AI's growth during this time more impressive (1h2m27s).
• Data analytics and understanding the user journey are top priorities for almost every company, which will continue to drive demand for Command AI's services (1h2m8s).
• Command AI was the number one rated company on G2, surpassing much larger companies, due to its unique experience and offerings (1h2m43s).
• This achievement is particularly notable given the increased scrutiny in software buying decisions, making Command AI's growth and success more impressive (1h2m31s).
• Amplitude's acquisition of Command AI is expected to be a successful partnership, with both companies excited to work together (1h3m0s).
• Spencer Skates, from Amplitude, can be found on Twitter, although the Twitter search function can be unreliable (1h3m26s).